WO2023107965A1

WO2023107965A1 - Salt and solid forms of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (dom), 2,5-dimethoxy-4-iodoamphetamine (doi), 2,5-dimethoxy-4-bromoamphetamine (dob), and 2,5-dimethoxy-4-chloroamphetamine (doc)

Info

Publication number: WO2023107965A1
Application number: PCT/US2022/081040
Authority: WO
Inventors: Matthew Duncton; Samuel CLARK
Original assignee: Terran Biosciences Inc
Current assignee: Terran Biosciences Inc
Priority date: 2021-12-06
Filing date: 2022-12-06
Publication date: 2023-06-15
Anticipated expiration: 2024-06-06

Abstract

Disclosed herein are salts and solid forms of DOM, DOI, DOB, and DOC. The solid form may be a salt and/or a crystalline form of the DOM, DOI, DOB, or DOC, such as a polymorph of DOM, DOI, DOB, or DOC, or a salt thereof. Also disclosed are methods for making the solid forms and methods for administering the solid forms. The disclosed solid forms of DOM, DOI, DOB, and DOC are useful for treating neurological disease and/or a psychiatric disorder in a subject.

Description

SALT AND SOLID FORMS OF 1-(2,5-DIMETHOXY-4-METHYLPHENYL)-2- AMINOPROPANE (DOM), 2,5-DIMETHOXY-4-IODOAMPHETAMINE (DOI), 2,5- DIMETHOXY-4-BROMOAMPHETAMINE (DOB), AND 2,5-DIMETHOXY-4- CHLOROAMPHETAMINE (DOC) CROSS REFERENCE TO RELATED APPLICATIONS This application claims priority to and the benefit of U.S. Provisional Application Nos. 63/286,405, filed on December 6, 2021, 63/286,415, filed on December 6, 2021, 63/286,419, filed on December 6, 2021, 63/286,491, filed on December 6, 2021, 63/326,753, filed on April 1, 2022, and 63/367,450, filed on June 30, 2022, all of which are incorporated by reference herein in their entirety for all purposes. SUMMARY Disclosed herein are solid forms of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), 2,5-dimethoxy-4-iodoamphetamine (DOI), 2,5-dimethoxy-4-bromoamphetamine (DOB), and 2,5-dimethoxy-4-chloroamphetamine (DOC), including salts, solid forms of the compound and salts thereof, as well as polymorphs of solid forms. Also disclosed are methods for making the solid forms and methods for using the solid forms of DOM, DOI, DOB, or DOC. In some embodiments, the solid form of DOM, DOI, DOB, or DOC is a polymorph of the free base form of the compound. In other embodiments, the solid form of DOM, DOI, DOB, or DOC is a salt, and maybe a polymorph of the salt. The salt may be formed from an acid selected from hydrochloric acid, fumaric acid, galactaric (mucic) acid, naphthalene-1,5-disulfonic acid, citric acid, sulfuric acid, d-glucuronic acid, ethane-1,2- disulfonic acid, lactobionic acid, p-toluenesulfonic acid, D-glucoheptonic acid, thiocyanic acid, (-)-L-pyroglutamic acid, methanesulfonic acid, L-malic acid, dodecylsulfuric acid, hippuric acid, naphthalene-2-sulfonic acid, D-gluconic acid, benzenesulfonic acid, D,L-lactic acid, oxalic acid, oleic acid, glycerophosphoric acid, succinic acid, ethanesulfonic acid 2-hydroxy, glutaric acid, L- aspartic acid, cinnamic acid, maleic acid, adipic acid, phosphoric acid, sebacic acid, ethanesulfonic acid, (+)-camphoric acid, glutamic acid, acetic acid, xinafoic acid, or a combination thereof. In any embodiments, a stoichiometric ratio of acid to DOM, DOI, DOB, or DOC is from about 0.4 to about 2.2, such as from about 0.5 to about 2, or from about 0.5, 1 or 2. In any embodiments, the solid form may be a crystalline solid, a hydrate, or a combination thereof. The crystalline solid may be substantially a single form, such as a polymorph form. And the polymorph may be selected to have one or more desired properties, particularly improved properties, such as physical properties, chemical properties, pharmacokinetic properties, or a combination thereof. The one or more desired properties may comprise melting point, glass transition temperature, flowability, thermal stability, mechanical stability, shelf life, stability against polymorphic transition, hygroscopic properties, solubility in water and/or organic solvents, reactivity, compatibility with excipients and/or delivery vehicles, bioavailability, absorption, distribution, metabolism, excretion, toxicity including cytotoxicity, dissolution rate, half-life, or a combination thereof. Also disclosed herein are embodiments of a pharmaceutical composition, comprising a solid form of a disclosed compound, and a pharmaceutically acceptable excipient. A method for administering the solid form of DOM, DOI, DOB, or DOC also is disclosed herein. In some embodiments, the method comprises administering to a subject an effective amount of a solid form of DOM, DOI, DOB, or DOC, or a pharmaceutical composition thereof. In some embodiments, the subject is suffering from a neurological disease or a psychiatric disorder, or both, such as a neurodegenerative disorder. The neurological disorder or psychiatric disorder, or both, may comprise depression, addiction, anxiety, or a post-traumatic stress disorder, and/or the neurological disorder or psychiatric disorder, or both, may comprise treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, or substance use disorder. In some embodiments, the neurological disorder or psychiatric disorder, or both, comprises stroke, traumatic brain injury, or a combination thereof. The method may comprise further comprising administering an effective amount of an empathogenic agent and/or a 5-HT_2A antagonist to the subject. The 5-HT_2A antagonist may be selected from MDL-11,939, eplivanserin (SR-46,349), ketanserin, ritanserin, altanserin, acepromazine, mianserin, mirtazapine, quetiapine, SB204741, SB206553, SB242084, LY272015, SB243213, blonanserin, SB200646, RS102221, nefazodone, MDL-100,907, pimavanserin, nelotanserin and lorcaserin. In any embodiments, administering the solid form of the compound comprises oral, parenteral, or topical administration. In certain embodiments, oral administration is used, but in other particular embodiments, administration is by injection, inhalation, intraocular, intravaginal, intrarectal or transdermal routes. The foregoing and other objects and features of the present disclosure will become more apparent from the following detailed description, which proceeds with reference to the accompanying figures. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 provides an XRPD diffractogram of DOM L-aspartate salt. FIG. 2 provides an XRPD diffractogram of DOM adipate salt. FIG. 3 provides an XRPD diffractogram of DOM benzenesulfonate (besylate) salt. FIG. 4 provides an XRPD diffractogram of DOM fumarate salt Form 1. FIG.5 provides an XRPD diffractogram of DOM gentisate salt. FIG. 6 provides an XRPD diffractogram of DOM glutamate salt. FIG. 7 provides an XRPD diffractogram of DOM glutarate salt Form 1. FIG. 8 provides an XRPD diffractogram of DOM glycolate salt Form 1. FIG. 9 provides an XRPD diffractogram of DOM hydrochloride salt. FIG.10 provides an XRPD diffractogram of DOM 1-hydroxy-2-napthoate (xinafoate) salt. FIG. 11 provides an XRPD diffractogram of DOM L-malate salt Form 1. FIG. 12 provides an XRPD diffractogram of a mixture of DOM maleate salt Forms 1 and 2. FIG. 13 provides an XRPD diffractogram of DOM malonate salt Form 1. FIG. 14 provides an XRPD diffractogram of DOM mesylate salt. FIG. 15 provides an XRPD diffractogram of a mixture of DOM mucate salt and mucic acid. FIG. 16 provides an XRPD diffractogram of DOM phosphate salt. FIG. 17 provides an XRPD diffractogram of DOM sulfate salt. FIG. 18 provides an XRPD diffractogram of DOM succinate salt. FIG. 19 provides an XRPD diffractogram of DOM L-tartrate salt Form 1. FIG. 20 provides an XRPD diffractogram of DOM tosylate salt Form 1. FIG. 21 provides an XRPD diffractogram of DOM mucate salt. FIG. 22 provides an XRPD diffractogram of DOM ethanesulfonate (esylate) salt. FIG. 23 provides an XRPD diffractogram of DOM lactate salt. FIG.24 provides a ¹H NMR spectrum for DOM adipate. FIG.25 provides TGA and DSC profiles for DOM adipate. FIG.26 provides a ¹H NMR spectrum for DOM benzenesulfonate. FIG. 27 provides TGA and DSC profiles for DOM benzenesulfonate. FIG.28 provides a ¹H NMR spectrum for DOM ethanesulfonate (esylate). FIG. 29 provides TGA and DSC profiles for DOM ethanesulfonate (esylate). FIG.30 provides a ¹H NMR spectrum for DOM glutamate. FIG.31 provides TGA and DSC profiles for DOM glutamate. FIG.32 provides a ¹H NMR spectrum for DOM glutarate Form 1. FIG.33 provides TGA and DSC profiles for DOM glutarate Form 1. FIG.34 provides a ¹H NMR spectrum for DOM glutarate Form 2. FIG.35 provides TGA and DSC profiles for DOM glutarate Form 2. FIG.36 provides a ¹H NMR spectrum for DOM glycolate Form 1. FIG.37 provides TGA and DSC profiles for DOM glycolate Form 1. FIG.38 provides a ¹H NMR spectrum for DOM hydrochloride. FIG. 39 provides TGA and DSC profiles for DOM hydrochloride. FIG.40 provides a ¹H NMR spectrum for DOM lactate. FIG.41 provides TGA and DSC profiles for DOM lactate. FIG.42 provides a ¹H NMR spectrum for DOM L-malate Form 1. FIG. 43 provides TGA and DSC profiles for DOM L-malate Form 1. FIG.44 provides a ¹H NMR spectrum for DOM maleate Form 1. FIG.45 provides TGA and DSC profiles for DOM maleate Form 1. FIG.46 provides a ¹H NMR spectrum for DOM malonate Form 1. FIG. 47 provides TGA and DSC profiles for DOM malonate Form 1. FIG.48 provides a ¹H NMR spectrum for DOM mucate. FIG.49 provides TGA and DSC profiles for DOM mucate. FIG.50 provides a ¹H NMR spectrum for DOM phosphate. FIG.51 provides TGA and DSC profiles for DOM phosphate. FIG.52 provides a ¹H NMR spectrum for DOM succinate. FIG.53 provides TGA and DSC profiles for DOM succinate. FIG.54 provides a ¹H NMR spectrum for DOM sulfate. FIG.55 provides TGA and DSC profiles for DOM sulfate. FIG.56 provides a ¹H NMR spectrum for DOM L-tartrate Form 1. FIG. 57 provides TGA and DSC profiles for DOM L-tartrate Form 1. FIG.58 provides a ¹H NMR spectrum for DOM tosylate Form 1. FIG.59 provides TGA and DSC profiles for DOM tosylate Form 1. FIG.60 provides a ¹H NMR spectrum for DOM 1-hydroxy-2-naphthoate (xinafoate). FIG.61 provides TGA and DSC profiles for DOM 1-hydroxy-2-naphthoate (xinafoate). FIG. 62 provides an XRPD diffractogram of DOM benzenesulfonate. FIG. 63 provides an XRPD diffractogram of DOM fumarate Form 2. FIG. 64 provides an XRPD diffractogram of DOM glutarate Form 2. FIG. 65 provides an XRPD diffractogram of DOM maleate Form 1. FIG. 66 provides an XRPD diffractogram of DOM malonate Form 1. FIG. 67 provides an XRPD diffractogram of DOM malonate Form 2. FIG. 68 provides an XRPD diffractogram of DOM phosphate. FIG. 69 provides an XRPD diffractogram of DOM sulfate. FIG. 70 provides an XRPD diffractogram of DOM L-tartrate Form 1. FIG. 71 provides an XRPD diffractogram of DOM tosylate Form 2.FIG. 72 provides an XRPD diffractogram of DOM Form A.FIG.73 provides an XRPD diffractogram of DOM Form A post-DVS analysis. FIG.74 provides a ¹

NMR spectrum for DOM Form A. FIG.75 provides TGA and DSC profiles for DOM Form A. FIG.76 provides an FT-IR spectrum for DOM Form A. FIG. 77 provides an XRPD diffractogram of a mixture of DOM L-malate Forms 1 and 2. FIG. 78 provides an XRPD diffractogram of DOM L-malate Form 3. FIG. 79 provides an XRPD diffractogram of DOI HCl. FIG. 80 provides an overlay of XRPD diffractograms of DOM L-malate Form 3 (top), DOM L-malate Forms 1 and 2 (middle), and DOM L-malate Form 1 (bottom). FIG.81 provides the DSC profile of the first heating cycle of DOM L-malate Form 1. FIG.82 provides the DSC profile of the second heating cycle of DOM L-malate Form 1. FIG.83 provides the DSC profile of the third heating cycle of DOM L-malate Form 1. FIG. 84 provides the modulated DSC profile of the non-crystalline L-malate salt. FIG.85 provides the DVS isotherm of DOM glycolate Form 1. FIG. 86 provides the DVS isotherm of DOM L-malate Form 1. FIG.87 provides the DVS isotherm of DOM hydrochloride. DETAILED DESCRIPTION I. Definitions The following explanations of terms and methods are provided to better describe the present disclosure and to guide those of ordinary skill in the art in the practice of the present disclosure. The singular forms “a,” “an,” and “the” refer to one or more than one, unless the context clearly dictates otherwise. The term “or” refers to a single element of stated alternative elements or a combination of two or more elements, unless the context clearly indicates otherwise. As used herein, “comprises” means “includes.” Thus, “comprising A or B,” means “including A, B, or A and B,” without excluding additional elements. All references, including patents and patent applications cited herein, are incorporated by reference in their entirety, unless otherwise specified. Unless otherwise indicated, all numbers expressing quantities of components, molecular weights, percentages, temperatures, times, and so forth, as used in the specification or claims, are to be understood as being modified by the term “about.” Accordingly, unless otherwise indicated, implicitly or explicitly, the numerical parameters set forth are approximations that may depend on the desired properties sought and/or limits of detection under standard test conditions/methods. When directly and explicitly distinguishing embodiments from discussed prior art, the embodiment numbers are not approximates unless the word “about” is expressly recited. Unless explained otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present disclosure, suitable methods and materials are described below. The materials, methods, and examples are illustrative only and not intended to be limiting. “Administering” refers to any suitable mode of administration, including, oral administration, administration as a suppository, topical contact, parenteral, intravenous, intraperitoneal, intramuscular, intralesional, intranasal or subcutaneous administration, intrathecal administration, or the implantation of a slow-release device e.g., a mini-osmotic pump, to the subject. “DOM” refers to the compound 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. The compound may also be referred to as 1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine, 2,5-dimethoxy-4-methylamphetamine, or 2,5-DOM.

“DOI” refers to the compound 2,5-dimethoxy-4-iodoamphetamine. The compound may also be referred to as 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine, 2-(4-iodo-2,5- dimethoxyphenyl)-1-methylethylamine, or 4-DOI.

“DOB” refers to the compound 2,5-dimethoxy-4-bromoamphetamine. The compound may also be referred to as 1-(4-bromo-2,5-dimethoxyphenyl)propan-2-amine, 4-bromo-2,5- dimethoxyamphetamine, or 4-Bromo-DMA.

DOB “DOC” refers to the compound 1-(4-chloro-2,5-dimethoxyphenyl)propan-2-amine. The compound may also be referred to as 2,5-dimethoxy-4-chloroamphetamine.

“Subject” refers to an animal, such as a mammal, including, but not limited to, primates (e.g., humans), cows, sheep, goats, horses, dogs, cats, rabbits, rats, mice and the like. In certain embodiments, the subject is a human subject. “Therapeutically effective amount” or “therapeutically sufficient amount” or “effective or sufficient amount” refers to a dose that produces therapeutic effects for which it is administered. The exact dose will depend on the purpose of the treatment, and will be ascertainable by one skilled in the art using known techniques (see, e.g., Lieberman, Pharmaceutical Dosage Forms (vols.1-3, 1992); Lloyd, The Art, Science and Technology of Pharmaceutical Compounding (1999); Pickar, Dosage Calculations (1999); and Remington: The Science and Practice of Pharmacy, 20th Edition, 2003, Gennaro, Ed., Lippincott, Williams & Wilkins). In sensitized cells, the therapeutically effective dose can often be lower than the conventional therapeutically effective dose for non-sensitized cells. “Neuronal plasticity” refers to the ability of the brain to change its structure and/or function continuously throughout a subject’s life. Examples of the changes to the brain include, but are not limited to, the ability to adapt or respond to internal and/or external stimuli, such as due to an injury, and the ability to produce new neurites, dendritic spines, and synapses. “Brain disorder” refers to a neurological disorder which affects the brain’s structure and function. Brain disorders can include, but are not limited to, Alzheimer’s, Parkinson’s disease, psychological disorder, depression, treatment resistant depression, addiction, anxiety, post- traumatic stress disorder, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, and substance use disorder. “Combination therapy” refers to a method of treating a disease or disorder, wherein two or more different pharmaceutical agents are administered in overlapping regimens so that the subject is simultaneously exposed to both agents. For example, the compounds of the present disclosure can be used in combination with other pharmaceutically active compounds. The compounds of the disclosure can be administered simultaneously (as a single preparation or separate preparation) or sequentially to the other drug therapy. In general, a combination therapy envisions administration of two or more drugs during a single cycle or course of therapy. “Neurotrophic factors” refers to a family of soluble peptides or proteins which support the survival, growth, and differentiation of developing and mature neurons. “Modulate” or “modulating” or “modulation” refers to an increase or decrease in the amount, quality, or effect of a particular activity, function or molecule. By way of illustration and not limitation, agonists, partial agonists, antagonists, and allosteric modulators (e.g., a positive allosteric modulator) of a G protein-coupled receptor (e.g., 5HT_2A) are modulators of the receptor. “Agonism” refers to the activation of a receptor or enzyme by a modulator, or agonist, to produce a biological response. “Agonist” refers to a modulator that binds to a receptor or enzyme and activates the receptor to produce a biological response. By way of example only, “5HT_2A agonist” can be used to refer to a compound that exhibits an EC50 with respect to 5HT_2A activity of no more than about 100 mM. In some embodiments, the term “agonist” includes full agonists or partial agonists. “Full agonist” refers to a modulator that binds to and activates a receptor with the maximum response that an agonist can elicit at the receptor. “Partial agonist” refers to a modulator that binds to and activates a given receptor, but has partial efficacy, that is, less than the maximal response, at the receptor relative to a full agonist. “Positive allosteric modulator” refers to a modulator that binds to a site distinct from the orthosteric binding site and enhances or amplifies the effect of an agonist. “Antagonism” refers to the inactivation of a receptor or enzyme by a modulator, or antagonist. Antagonism of a receptor, for example, is when a molecule binds to the receptor and does not allow activity to occur. “Antagonist” or “neutral antagonist” refers to a modulator that binds to a receptor or enzyme and blocks a biological response. An antagonist has no activity in the absence of an agonist or inverse agonist but can block the activity of either, causing no change in the biological response. “Composition” refers to a product comprising the specified ingredients in the specified amounts, as well as any product, which results, directly or indirectly, from combination of the specified ingredients in the specified amounts. By “pharmaceutically acceptable” it is meant the carrier, diluent or excipient must be compatible with the other ingredients of the formulation. “Pharmaceutically acceptable excipient” refers to a substance that aids the administration of an active agent to and absorption by a subject. Pharmaceutical excipients useful in the present disclosure include, but are not limited to, binders, fillers, disintegrants, lubricants, coatings, sweeteners, flavors and colors. One of skill in the art will recognize that other pharmaceutical excipients are useful in the present disclosure. II. Compounds Disclosed herein are solid forms of DOM, DOI, DOB, and DOC that are useful to treat various disorders, such as brain disorders. Also disclosed are methods for making the solid forms of DOM, DOI, DOB, or DOC and method of administering the solid forms of DOM, DOI, DOB, or DOC.

In some embodiments, the solid form of the compound is a crystalline form of DOM, DOI, DOB, or DOC. In some embodiments, the solid form of the compound is a salt of the compound. In some embodiments, the solid form of DOM is a polymorph of DOM, such as a polymorph of the free base compound or a polymorph of the salt. In some embodiments, the solid form of DOI is a polymorph of DOI, such as a polymorph of the free base compound or a polymorph of the salt. In some embodiments, the solid form of DOB is a polymorph of DOB, such as a polymorph of the free base compound or a polymorph of the salt. In some embodiments, the solid form of DOC is a polymorph of DOC, such as a polymorph of the free base compound or a polymorph of the salt. In some embodiments, the solid form of the compound is a crystalline salt form of the compound, such as an acid addition salt form. A) Salts In some embodiments, the solid form of DOM, DOI, DOB, or DOC comprises a salt of DOM, DOI, DOB, or DOC. Suitable salts include a pharmaceutically acceptable salt of DOM, DOI, DOB, or DOC. In some embodiments, the salt is not a hydrochloride salt of DOM, DOI, DOB, or DOC. In some embodiments, the salt of DOM, DOI, DOB, or DOC may be formed from a suitable pharmaceutically acceptable acid, including, without limitation, inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like, as well as organic acids such as formic acid, acetic acid, trifluoroacetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, maleic acid, malonic acid, succinic acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, benzene sulfonic acid, isethionic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicylic acid, xinafoic acid and the like. In other embodiments, the salt of DOM, DOI, DOB, or DOC may be formed from a suitable pharmaceutically acceptable base, including, without limitation, inorganic bases such as sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, aluminum salts and the like. Salts derived from pharmaceutically acceptable organic bases include, but are not limited to, salts of primary, secondary, and tertiary amines, substituted amines including naturally occurring substituted amines, cyclic amines and basic ion exchange resins, such as isopropylamine, trimethylamine, diethylamine, triethylamine, tripropylamine, tris(hydroxymethyl)aminomethane (Tris), ethanolamine, 2-dimethylaminoethanol, 2- diethylaminoethanol, dicyclohexylamine, lysine, arginine, histidine, caffeine, procaine, hydrabamine, choline, betaine, ethylenediamine, glucosamine, methylglucamine, theobromine, purines, piperazine, piperidine, N-ethylpiperidine, polyamine resins, and the like. Additional information concerning pharmaceutically acceptable salts can be found in, for example, S. M. Berge, et al., “Pharmaceutical Salts,” J. Pharm. Sci., 1977; 66:1-19 which is incorporated herein by reference. In some embodiments, the salt may be formed using an acid from Table 1.

In some embodiments, the acid is not hydrochloric acid. The acid salts of DOM, DOI, DOB, or DOC disclosed herein can have any suitable stoichiometric ratio of acid to DOM, DOI, DOB, or DOC. In one embodiment, the molar ratio of acid to DOM, DOI, DOB, or DOC is from about 0.4 to about 2.2, such as forms wherein the salt has a stoichiometric ratio of acid to DOM, DOI, DOB, or DOC of from about 0.5 to about 2, such as about 0.5, about 1 or about 2. B) Solid forms Embodiments of DOM, DOI, DOB, or DOC of the present disclosure are in a solid form. The solid form may be a crystalline form or an amorphous form. In some embodiments, the solid form is a crystalline form, such as a polymorph. In some embodiments, the solid form of DOM, DOI, DOB, or DOC is a salt. And in certain embodiments, the solid form is a crystalline salt form of the compound. A person of ordinary skill in the art understands that solid forms of DOM, DOI, DOB, or DOC such as crystalline forms including salt and non-salt crystalline forms of DOM, DOI, DOB, or DOC , may exist in more than one crystal form. Such different forms are referred to as polymorphs. In some embodiments, the disclosed compounds are particular polymorphs of DOM or DOM salts. In some embodiments, the disclosed compounds are particular polymorphs of DOI or DOI salts. In some embodiments, the disclosed compounds are particular polymorphs of DOB or DOB salts. In some embodiments, the disclosed compounds are particular polymorphs of DOC or DOC salts. In some embodiments, the solid form of DOM, DOI, DOB, or DOC disclosed herein is selected to be a crystalline form, such as a particular polymorph of a crystalline form of DOM, DOI, DOB, or DOC that provides one or more desired properties. In one embodiment, the crystalline form offers advantages over the amorphous form of the molecule. In another embodiment, the disclosed polymorph offers improved properties as compared to another polymorph of DOM, DOI, DOB, or DOC . The DOM, DOI, DOB, or DOC may be a salt or free base compound. The one or more desired properties may include, but are not limited to, physical properties, including but not limited to, melting point, glass transition temperature, flowability, and/or stability, such as thermal stability, mechanical stability, shelf life, stability against polymorphic transition, etc.; chemical properties, such as, but not limited to, hygroscopic properties, solubility in water and/or organic solvents, reactivity, compatibility with excipients and/or delivery vehicles; and/or pharmacokinetic properties, such as, but not limited to, bioavailability, absorption, distribution, metabolism, excretion, toxicity including cytotoxicity, dissolution rate, and/or half-life. The desired polymorph may be produced by techniques known to persons of ordinary skill in the art. Such techniques include, but are not limited to, crystallization in particular solvents and/or at particular temperatures, supersaturation, using a precipitation agent, such as a salt, glycol, alcohol, etc., co-crystallization, lyophilization, spray drying, freeze drying, and/or complexing with an inert agent. Techniques to identify a particular solid form of DOM, DOI, DOB, or DOC are known to persons of ordinary skill in the art, and include, but are not limited to, X-ray crystallography, X- ray diffraction, electron crystallography, powder diffraction, including X-ray, neutron, or electron diffraction, X-ray fiber diffraction, small-angle X-ray scattering, and/or melting point.

DOM, DOI, DOB, DOC, and salts and solid forms thereof

Solid forms of DOM L-aspartate

In some embodiments, the present disclosure provides solid forms of DOM L-aspartate, e.g., crystalline forms of DOM L-aspartate. In some embodiments, the DOM L-aspartate XRPD profile is substantially similar to that shown in FIG. 1.

In some embodiments, the solid form of DOM L-aspartate is crystalline DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.8 °2θ, 11.3 °2θ, and 12.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-aspartate is crystalline DOM L-aspartate characterized, by XRPD signals at 3.8 °2θ, 11.3 2θ. and 12.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-aspartate is crystalline DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.8 °2θ, 7.6 °2θ, 11.3 °2θ, 12.4 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-aspartate is crystalline DOM L- aspartate characterized by XRPD signals at 3.8 °2θ, 7.6 °2θ, 11.3 °2θ, 12.4 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-aspartate is crystalline DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.8 °2θ, 11.3 °2θ, and 21.4 °2θ (±0,2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-aspartate is crystalline DOM L-aspartate characterized by XRPD signals at 3.8 °2θ, 11.3 °2θ, and 21.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-aspartate is crystalline DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of‘3.8 °2θ, 11.3 °2θ, 11.8 °2θ, 21.4 °2θ, and 21.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-aspartate is DOM L-aspartate characterized by XRPD signals at 3.8 °2θ, 11.3 °2θ, 11.8 °2θ, 21.4 °2θ, and 21.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-aspartate is crystalline DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.8 °2θ, 11.3 °2θ, 21.4 °2θ, 21.6 °2θ, 1 1.8 °2θ, 23.8 °2θ, and 12.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-aspartate is DOM L-aspartate characterized by XRPD signals at 3.8 °2θ, 11.3 °2θ, 21.4 °2θ, 21.6 °2θ, 11.8 °2θ, 23.8 °2θ, and 12.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-aspartate is cry stalline DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.8 °2θ, 11.3 °2θ, 21.4 °2θ, 21.6 °2θ, 11.8 °2θ, 23.8 °2θ, 12.4 °2θ, 24.3 °2θ, 26.4 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-aspartate is DOM L-aspartate characterized by XRPD signals at 3.8 °2θ, 11.3 °2θ, 21.4 °2θ, 21.6 °2θ, 11.8 °2θ, 23.8 °2θ, 12.4 °2θ, 24.3 °2θ, 26.4 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 20; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM L-aspartate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, or twenty-nine XRPD signals selected from those set forth in Table 2.

Table 2. XRPD Signals for DOM L-aspartate

Solid forms of DOM adipate

In some embodiments, the present disclosure provides solid forms of DOM adipate, e.g., crystalline forms of DOM adipate. In some embodiments, the DOM adipate XRPD profile is substantially similar to that shown in FIG. 2. In some embodiments, the DOM adipate ¹H NMR spectrum is substantially similar to that shown in FIG. 24. In some embodiments, the DOM adipate TGA profile is substantially similar to that shown in FIG. 25. In some embodiments, the DOM adipate DSC profile is substantially similar to that shown in FIG. 25.

In some embodiments, the solid form of DOM adipate is crystalline DOM adipate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.4 °2θ, .12.8 °2θ, and .15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM adipate is crystalline DOM adipate characterized by XRPD signals at 9.4 °2θ, 12,8 °2θ, and 1.5.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM adipate is crystalline DOM adipate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.4 °2θ, 12.8 °2θ, 15.1 °2θ, 16.5 °2θ, and 17.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM adipate is crystalline DOM adipate characterized by XRPD signals at 9.4 °2θ, 12.8 °2θ, 15.1 °2θ, 16.5 °2θ, and 17.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM adipate is crystalline DOM adipate characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2θ, 22.5 °2θ, and 23.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±O.O °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM adipate is crystalline DOM adipate characterized by XRPD signals at 15.1 °2θ, 22.5 °2θ, and 23.0 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±O.O °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM adipate is crystalline DOM adipate characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2θ, 16.5 °2θ, 22.0 °2θ. 22.5 °2θ, and 23.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or .0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM adipate is DOM adipate characterized by XRPD signals at 15.1 °2θ, 16.5 °2θ, 22.0 °2θ, 22.5 °2θ, and 23.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM adipate is crystalline DOM adipate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 15.1 °2θ, 23.0 °2θ, 22.5 °2θ, 22.0 °2θ, 16.5 °2θ, 9.4 °2θ, and 15.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM adipate is DOM adipate characterized by XRPD signals at 15.1 °2θ, 23.0 °2θ, 22.5 °2θ, 22.0 °2θ, 16.5 °2θ, 9.4 °2θ, and. 15.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM adipate is crystalline DOM adipate characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2θ, 23.0 °2θ, 22.5 °2θ, 22.0 °2θ, 16.5 °2θ, 9.4 °2θ, 15.3 °2θ, 21.6 °2θ, 25.2 °2θ, and 18.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM adipate is DOM adipate characterized by XRPD signals at 15.1 °2θ, 23.0 °2θ, 22,5 °2θ, 22.0 °2θ, 16.5 °2θ, 9.4 °2θ, 15.3 °2θ, 21.6 °2θ, 25.2 °2θ, and 18.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM adipate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, or fifty XRPD signals selected from those set forth in Table 3.

Table 3, XRPD Signals for DOM adipate

Solid forms of DOM benzenesulfonate (besylate)

In some embodiments, the present disclosure provides solid, forms of DOM benzenesulfonate (besylate), e.g., crystalline forms of DOM benzenesulfonate. In some embodiments, the DOM benzenesulfonate XRPD profile is substantially similar to that shown in FIGs. 3 or 62. In some embodiments, the DOM benzenesulfonate ' H NMR spectrum is substantially similar to that shown in FIG. 26. In some embodiments, the DOM benzenesulfonate TGA profile is substantially similar to that shown in FIG. 27. In some embodiments, the DOM benzenesulfonate DSC profile is substantially similar to that shown in FIG. 27,

In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.5 °2θ, 9.1 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by XRPD signals at. 5.5 °2θ, 9.1 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.5 °2θ, 9.1 °2θ, 10.6 °2θ, l l.O °2θ, and 17.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by XRPD signals at 5.5 °2θ, 9.1 °2θ, 10.6 °2θ, 11.0 °2θ, and 17.7 °2θ (±0.2 °2θ. ±0.1 °2θ: or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.0 °2θ, 18.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by XRPD signals at 11.0 °2θ, 18.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.1 °2θ, 11.0 °2θ, 16.2 °2θ, 18.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM benzenesulfonate is DOM benzenesulfonate characterized by XRPD signals at 9.1 °2θ, 11.0 °2θ, 16.2 °2θ, 18.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

In some embodiments, the solid form of DOM benzenesulfonate is cry stalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.3 °2θ, 18.2 °2θ, 11.0 °2θ, 9.1 °2θ, 16.2 °2θ, 19.2 °2θ, and 5.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM benzenesulfonate is DOM benzenesulfonate characterized by XRPD signals at 20.3 °2θ, 18.2 °2θ, 11.0 °2θ, 9.1 °2θ, 16.2 °2θ, 19.2 °2θ, and 5.5 29 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.3 °2θ, 18.2 °2θ, 11.0 °2θ, 9.1 °2θ, 16.2 °2θ, 19.2 °2θ, 5.5 °2θ, 17.7 °2θ, 21.8 °2θ, and 24,6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM benzenesulfonate is DOM benzenesulfonate characterized by XRPD signals at 20.3 °2θ, 18.2 °2θ, 11.0 °2θ, 9.1 °2θ, 16.2 °2θ, 19.2 °2θ, 5.5 °2θ, 17.7 °2θ, 21.8 °2θ, and 24.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM benzenesulfonate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, thirty-six, thirty-seven, or thirty-eight XRPD signals selected from those set forth in Table 4.

Table 4. XRPD Signals for DOM benzenesulfonate (besylate)

In some embodiments, the solid form of DOM benzenesulfonate (besylate) is crystalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.1 °2θ, 19.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kai radiation). In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by XRPD signals at 9. 1 °2θ, 19.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.1 °2θ, 11.0 °2θ, 18.2 °2θ, 19.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM benzenesulfonate is DOM benzenesulfonate characterized by XRPD signals at 9.1 °2θ, 11.0 °2θ, 18.2 °2θ, 19.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM benzenesulfonate is cry stalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.1 °2θ, 20.3 °2θ, 19.2 °2θ, 18.2 °2θ, 11.0 °2θ, 24.9 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM benzenesulfonate is DOM benzenesulfonate characterized by XRPD signals at 9.1 °2θ, 20.3 °2θ,

19.2 °2θ, 18.2 °2θ, 11.0 °2θ, 24.9 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 20: Cu Kα1 radiation).

In some embodiments, the solid form of DOM benzenesulfonate is crystalline DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.1 °2θ, 20.3 °2θ, 19.2 °2θ, 18.2 °2θ, 11.0 °2θ, 24.9 °2θ, 10.6 °2θ, 21.8 °2θ,

16.2 °2θ, and 5.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM benzenesulfonate is DOM benzenesulfonate characteri zed by XRPD signals at 9.1 °2θ, 20.3 °2θ, 19.2 °2θ, 18.2 °2θ, 1 1.0 °2θ, 24.9 °2θ, 10.6 °2θ, 21.8 °2θ, 16.2 °2θ, and 5.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM benzenesulfonate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, fifty-one, fifty-two, or fifty -three XRPD signals selected from those set forth in Table 5.

Table 5. XRPD Signals for DOM benzenesulfonate (besyiate)

Solid forms of DOM fumarate Form 1

In some embodiments, the present disclosure provides solid forms of DOM fumarate Form 1 , e.g., crystalline forms of DOM fumarate. In some embodiments, the DOM fumarate Form 1 XRPD profile is substantially similar to that shown in FIG. 4.

In some embodiments, the solid form of DOM fumarate Form 1 is crystalline DOM fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2θ. 9.8 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 1 is crystalline DOM fumarate Form 1 characterized by XRPD signals at 4.9 °2θ, 9.8 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM fumarate Form 1 is crystalline DOM fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2θ, 9.8 °2θ, 10.6 °2θ, 14.6 °2θ, and 21.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 1 is crystalline DOM fumarate Form 1 characterized by XRPD signals at 4.9 °2θ, 9.8 °2θ, 10.6 °2θ, 14.6 °2θ, and. 21.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM fumarate Form 1 is crystalline DOM fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2θ, 9.8 °2θ, and 25.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 1 is crystalline DOM fumarate Form 1 characterized by XRPD signals at 4,9 °2θ, 9.8 °2θ, and 25.0 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 1 is crystalline DOM fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2θ, 9.8 °2θ, 14.6 °2θ, 21.6 °2θ, and 25.0 °2θ (±0.2 °2θ. ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 1 is DOM fumarate Form 1 characterized by XRPD signals at 4.9 °2θ, 9.8 °2θ, 14.6 °2θ, 21.6 °2θ, and 25.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM fumarate Form 1 is crystalline DOM fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.8 °2θ, 4.9 °2θ, 25.0 °2θ, 21.6 °2θ, 14.6 °2θ, 10.6 °2θ, and 19.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 1 is DOM fumarate Form 1 characterized by XRPD signals at 9.8 °2θ, 4.9 °2θ, 25.0 °2θ, 21.6 °2θ, 14.6 °2θ, 10.6 °2θ, and 19.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM fumarate Form 1 is crystalline DOM fumarate Form 1 characterized, by two or more, or three or more XRPD signals selected from the group consisting of 9.8 °2θ, 4.9 °2θ, 25.0 °2θ, 21.6 °2θ, 14.6 °2θ, 10.6 °2θ, 19.3 °2θ, 19.5 °2θ, 23.9 °2θ, and 19.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 1 is DOM fumarate Form 1 characterized by XRPD signals at 9.8 °2θ, 4.9 °2θ, 25.0 °2θ, 21.6 °2θ, 14.6 °2θ, 10.6 °2θ, 19.3 °2θ, 19.5 °2θ, 23.9 °2θ, and 19.0 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM fumarate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, or thirty XRPD signals selected from those set forth in Table 6.

Table 6. XRPD Signals for DOM fumarate Form 1

Solid forms of DOM fumarate Form 2

In some embodiments, the present disclosure provides solid forms of DOM fumarate Form 2, e.g., crystalline forms of DOM fumarate Form 2. In some embodiments, the DOM fumarate Form 2 XRPD profile is substantially similar to that shown in FIG. 63.

In some embodiments, the solid form of DOM fumarate Form 2 is crystalline DOM fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.2 °2θ. 4.7 °2θ, and 10.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 2 is crystalline DOM fumarate Form 2 characterized by XRPD signals at 4.2 °2θ, 4.7 °2θ, and 10.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM fumarate Form 2 is crystalline DOM fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.2 °2θ, 4.7 °2θ, 10.3 °2θ, 12.7 °2θ, and 15.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 2 is crystalline DOM fumarate Form 2 characterized by XRPD signals at 4.2 °2θ, 4.7 °2θ, 10.3 °2θ,

12.7 °2θ, and 15.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM fumarate Form 2 is crystalline DOM fumarate Form 2 characterized by two or more, or three or more XR PD signals selected from the group consisting of 4.7 °2θ. 12.7 °2θ, and 15.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 2 is crystalline DOM fumarate Form 2 characterized by XRPD signals at 4.7 °2θ, 12.7 °2θ, and 15.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM fumarate Form 2 is ciystalline DOM fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.7 °2θ, 12.7 29. 15.8 °2θ, 25.5 26. and 4.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 2 is DOM fumarate Form 2 characterized by XRPD signals at 4.7 °2θ, 12.7 °2θ, 15.8 °2θ, 25.5 °2θ, and. 4.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM fumarate Form 2 is ciystalline DOM fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.7 °2θ, 12.7 °2θ, 15.8 °2θ, 25.5 °2θ, 4.2 °2θ, 25.1 °2θ, and 19.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 2 is DOM fumarate Form 2 characterized by XRPD signals at 4.7 °2θ, 12.7 °2θ,

15.8 °2θ, 25.5 °2θ, 4.2 °2θ, 25.1 °2θ, and 19.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM fumarate Form 2 is crystalline DOM fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.7 °2θ, 12.7 °2θ, 15.8 °2θ, 25.5 °2θ, 4.2 °2θ, 25.1 °2θ, 19.1 °2θ, 20.8 °2θ,

22.8 °2θ, and 14.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ. Cu Kα1 radiation). In some embodiments, the solid form of DOM fumarate Form 2 is DOM fumarate Form 2 characterized by XRPD signals at 4.7 °2θ, 12.7 °2θ, 15.8 °2θ, 25.5 °2θ, 4.2 °2θ, 25.1 °2θ, 19.1 °2θ, 20.8 °2θ, 22.8 °2θ, and 14.2 °2θ (.±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the crystalline DOM fumarate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, or thirty-nine XRPD signals selected from those set forth in Table 7.

Table 7. XRPD Signals for DOM fumarate Form 2

Solid forms oj DOM gentisate

In some embodiments, the present disclosure provides solid forms of DOM gentisate, e.g., crystalline forms of DOM gentisate. In some embodiments, the DOM gentisate XRPD profile is substantially similar to that shown in FIG. 5.

In some embodiments, the solid form of DOM gentisate is crystalline DOM gentisate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 13.2 °2θ, 13.9 °2θ, and 17.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM gentisate is crystalline DOM gentisate characterized by XRPD signals at 13.2 °2θ, 13.9 20. and 17.6 20 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM gentisate is crystalline DOM gentisate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 13.2 °2θ, 13.9 °2θ, 15.5 °2θ, 17.6 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM gentisate is crystalline DOM gentisate characterized by XRPD signals at 13.2 °2θ, 13.9 °2θ, 15.5 °2θ, 17.6 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM gentisate is crystalline DOM gentisate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.6 °2θ, 26.5 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ, Cu Kα1 radiation). In some embodiments, the solid form of DOM gentisate is crystalline DOM gentisate characterized by XRPD signals at 17.6 °2θ, 26.5 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM gentisate is crystalline DOM gentisate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.6 °2θ, 26.5 °2θ, 22.0 °2θ, 23.5 °2θ, and 15.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM gentisate is DOM gentisate characterized by XRPD signals at 17.6 °2θ, 26.5 °2θ, 22.0 °2θ, 23.5 °2θ, and 15.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM gentisate is crystalline DOM gentisate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.6 °2θ, 26.5 °2θ, 22.0 °2θ, 23.5 °2θ, 15.5 °2θ, 18.4 °2θ, and 23.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM gentisate is DOM gentisate characterized by XRPD signals at 17.6 °2θ, 26.5 °2θ, 22.0 °2θ, 23.5 °2θ, 15.5 °2θ, 18.4 °2θ, and 23.9 °2θ (.±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM gentisate is crystalline DOM gentisate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.6 °2θ, 26.5 °2θ, 22.0 °2θ, 23.5 °2θ, 15.5 °2θ, 18.4 °2θ, 23.9 °2θ, 13.2 °2θ, 13.9 °2θ, and 22.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM gentisate is DOM gentisate characterized by XRPD signals at 17.6 °2θ, 26.5 °2θ, 22.0 °2θ, 23.5 29. 15.5 °2θ, 18.4 °2θ, 23.9 °2θ. 13.2 °2θ, 13.9 °2θ. and 22.3 °2θ (±0.2 29; ±0.1 29: or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM gentisate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, or fifteen XRPD signals selected from those set forth in Table 8.

Table 8, XRPD Signals for DOM gentisate

Solid forms of DOM glutamate

In some embodiments, the present disclosure provides solid forms of DOM glutamate, e.g., crystalline forms of DOM glutamate. In some embodiments, the DOM glutamate XRPD profile is substantially similar to that shown in FIG. 6. In some embodiments, the DOM glutamate ^]H NMR spectrum is substantially similar to that shown in FIG. 30. In some embodiments, the DOM glutamate TGA profile is substantially similar to that shown in FIG. 31. In some embodiments, the DOM glutamate DSC profile is substantially similar to that shown in FIG. 31.

In some embodiments, the solid form of DOM glutamate is crystalline DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 9.9 °2θ, and 13.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutamate is crystalline DOM glutamate characterized by XRPD signals at 3.4 °2θ, 9.9 °2θ, and 13.2 °2θ (±0,2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutamate is crystalline DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 9.9 °2θ, 13.2 °2θ, 16.6 °2θ, and 17.0 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutamate is crystalline DOM glutamate characterized by XRPD signals at 3.4 °2θ, 9.9 °2θ, 13.2 °2θ, 16.6 °2θ, and 17.0 °2θ (±0.2 °2θ;

±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutamate is crystalline DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 26.6 °2θ, and 17.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutamate is crystalline DOM glutamate characterized by XRPD signals at 3.4 °2θ, 26.6 °2θ, and 17.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutamate is crystalline DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 26.6 °2θ, 17.0 °2θ, 25.5 °2θ, and 13.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutamate is DOM glutamate characterized by XRPD signals at 3.4 °2θ, 26.6 °2θ, 17.0 °2θ, 25.5 °2θ, and 13.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutamate is crystalline DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 26.6 °2θ, 17.0 °2θ, 25.5 °2θ, 13.2 °2θ, 9.9 °2θ, and 33.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutamate is DOM glutamate characterized by XRPD signals at 3.4 °2θ, 26.6 °2θ, 17.0 °2θ, 25.5 °2θ, 13.2 °2θ, 9.9 °2θ, and 33.4 °2θ (.±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutamate is crystalline DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 26.6 °2θ, 17.0 °2θ, 25.5 °2θ, 13.2 °2θ, 9.9 °2θ, 33.4 °2θ, 25.2 °2θ, 30.0 °2θ, and 22.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutamate is DOM glutamate characterized, by XRPD signals at 3.4 °2θ, 26.6 °2θ, 17.0 °2θ, 25.5 °2θ, 13.2 °2θ, 9.9 °2θ, 33.4 °2θ, 25.2 °2θ, 30.0 °2θ, and 22.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM glutamate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, or thirty-nine XRPD signals selected from those set forth in Table 9.

Table 9. XRPD Signals for DOM glutamate

Solid forms of DOM glutarate Form 1

In some embodiments, the present disclosure provides solid forms of DOM glutarate Form 1 , e.g., crystalline forms of DOM glutarate Form 1. In some embodiments, the DOM glutarate Form 1 XRPD profile is substantially similar to that shown in FIG. 7. In some embodiments, the DOM glutarate Form 1 ^lH NMR spectrum is substantially similar to that shown in FIG. 32. In some embodiments, the DOM glutarate Form 1 TGA profile is substantially similar to that shown m FIG. 33. In some embodiments, the DOM glutarate Form 1 DSC profile is substantially similar to that shown in FIG. 33. In some embodiments, the solid form of DOM glutarate Form 1 is crystalline DOM glutarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 5.9 °2θ, and 8.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 1 is crystalline DOM glutarate Form 1 characterized by XRPD signals at 4.1 °2θ, 5.9 °2θ, and 8.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutarate Form 1 is crystalline DOM glutarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ. 5.9 °2θ, 8.1 °2θ, 9.0 °2θ, and 12.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 1 is crystalline DOM glutarate Form 1 characterized by XRPD signals at 4.1 °2θ, 5.9 °2θ, 8.1 °2θ, 9.0 °2θ, and 12.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutarate Form 1 is crystalline DOM glutarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2θ, 21.8 °2θ, and 5.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 1 is crystalline DOM glutarate Form 1 characterized by XRPD signals at 12.1 °2θ, 21.8 °2θ, and 5.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutarate Form 1 is crystalline DOM glutarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12. 1 °2θ, 21.8 °2θ, 5.9 °2θ, 18.6 °2θ, and 8,1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 1 is DOM glutarate Form 1 characterized by XRPD signals at 12.1 °2θ, 21.8 °2θ, 5.9 °2θ, 18.6 °2θ, and 8.1 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutarate Form 1 is crystalline DOM glutarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2θ, 21.8 °2θ, 5.9 °2θ, 18.6 °2θ, 8.1 °2θ, 22.5 °2θ, and 15.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 1 is DOM glutarate Form 1 characterized by XRPD signals at 12.1 °2θ, 21.8 °2θ, 5.9 °2θ, 18.6 °2θ, 8. 1 °2θ, 22.5 °2θ, and 15.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 1 is crystalline DOM glutarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2θ, 21.8 °2θ, 5.9 °2θ, 18.6 °2θ, 8.1 °2θ, 22.5 °2θ, 15.4 °2θ, 4.1 °2θ, 23.7 °2θ, and 14.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 1 is DOM glutarate Form 1 characterized by XR PD signals at 12.1 °2θ, 21.8 °2θ, 5.9 °2θ, 18.6 °2θ, 8.1 °2θ, 22.5 °2θ, 15.4 °2θ, 4.1 °2θ, 23.7 °2θ, and 14.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM glutarate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, or forty-eight XRPD signals selected from those set forth in Table 10.

Table 10. XRPD Signals for DOM glutarate Form 1

Solid forms of DOM glutarate Form 2

In some embodiments, the present disclosure provides solid, forms of DOM glutarate Form 2, e.g., crystalline forms of DOM glutarate Form 2. In some embodiments, the DOM glutarate Form 2 XRPD profile is substantially similar to that shown in FIG. 64. In some embodiments, the DOM glutarate Form 2 NMR spectrum is substantially similar to that shown in FIG. 34. In some embodiments, the DOM glutarate Form 2 TGA profile is substantially similar to that shown in FIG, 35. In some embodiments, the DOM glutarate Form 2 DSC profile is substantially similar to that shown in FIG. 35,

In some embodiments, the solid form of DOM glutarate Form 2 is crystalline DOM glutarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 8.5 °2θ, and 10.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 2 is crystalline DOM glutarate Form 2 characterized by XRPD signals at 6. 1 °2θ, 8.5 °2θ, and 10.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutarate Form 2 is crystalline DOM glutarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 8.5 °2θ. 10.5 °2θ, 12.1 °2θ, and 19.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 2 is crystalline DOM glutarate Form 2 characterized by XRPD signals at 6.1 °2θ, 8.5 °2θ, 10.5 °2θ, 12.1 °2θ, and 19.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutarate Form 2 is crystalline DOM glutarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 16.4 °2θ, and 19.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 2 is crystalline DOM glutarate Form 2 characterized, by XRPD signals at 6.1 °2θ, 16.4 °2θ, and. 19.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutarate Form 2 is crystalline DOM glutarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6, 1 °2θ, 16.4 °2θ, 19.8 °2θ, 15.6 °2θ, and 21.0 °2θ (±0,2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1. radiation). In some embodiments, the solid form of DOM glutarate Form 2 is DOM glutarate Form 2 characterized by XRPD signals at 6.1 °2θ, 16.4 °2θ, 19.8 °2θ, 1.5.6 °2θ, and 21.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1. radiation).

In some embodiments, the solid form of DOM glutarate Form 2 is crystalline DOM glutarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 16.4 °2θ, 19.8 °2θ, 15.6 °2θ, 21.0 °2θ, 8.5 °2θ, and 16.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 2 is DOM glutarate Form 2 characterized by XRPD signals at 6.1 °2θ, 16.4 °2θ, 19.8 °2θ, 15.6 °2θ, 21.0 °2θ, 8.5 °2θ, and 16.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glutarate Form 2 is crystalline DOM glutarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 16.4 °2θ, 19.8 °2θ, 15.6 °2θ, 21.0 °2θ, 8.5 °2θ, 16.0 °2θ, 12.1 °2θ, 23.2 °2θ, and 23.8 °2θ (±0.2 °2θ. ±0.1 °2θ. or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glutarate Form 2 is DOM glutarate Form 2 characterized by XRPD signals at 6.1 °2θ, 16.4 °2θ, 19.8 °2θ, 15.6 °2θ, 21.0 °2θ, 8.5 °2θ, 16.0 °2θ, 12.1 °2θ, 23.2 °2θ, and 23.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM glutarate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, or fifty-six XRPD signals selected from those set forth in Table 11.

Table 11, XRPD Signals for DOM glutarate Form 2

Solid forms of DOM glycolate Form 1

In some embodiments, the present disclosure provides solid forms of DOM glycolate Form 1, e.g., crystalline forms of DOM glycolate Form 1. In some embodiments, the DOM glycolate Form 1 XRPD profile is substantially similar to that shown in FIG. 8. In some embodiments, the DOM glycolate Form 1 ^lH NMR spectrum is substantially similar to that shown in FIG. 36. In some embodiments, the DOM glycolate Form 1 TGA profile is substantially similar to that shown in FIG. 37. In some embodiments, the DOM glycolate Form 1 DSC profile is substantially similar to that shown in FIG. 37.

In some embodiments, the solid form of DOM glycolate Form 1 is crystalline DOM glycolate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ. 10.1 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glycolate Form 1 is crystalline DOM glycolate Form 1 characterized by XRPD signals at 5.1 °2θ, 10.1 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glycolate Form 1 is crystalline DOM glycolate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 10.1 29. 15.1 °2θ, 20.2 29. and 25.3 29 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glycolate Form 1 is crystalline DOM glycolate Form 1 characterized by XRPD signals at 5.1 °2θ, 10.1 °2θ, 15.1 °2θ, 20.2 °2θ, and. 25.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glycolate Form 1 is crystalline DOM glycolate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 15.1 °2θ, and 20.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glycolate Form 1 is crystalline DOM glycolate Form 1 characterized by XRPD signals at 5. 1 °2θ, 15.1 °2θ, and 20.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glycolate Form 1 is crystalline DOM glycolate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 15.1 °2θ, 20.2 °2θ, 25.3 °2θ, 10. 1 °2θ, 22.6 °2θ, and 14.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glycolate Form 1 is DOM glycolate Form 1 characterized by XRPD signals at 5.1 °2θ, 15.1 °2θ,

20.2 °2θ, 25.3 °2θ, 10.1 °2θ, 22.6 °2θ, and 14.2 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM glycolate Form 1 is crystalline DOM glycolate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ. 15.1 °2θ, 20.2 °2θ, 25.3 °2θ, 10.1 °2θ, 22.6 °2θ, 14.2 °2θ, 18.1 °2θ.

24.3 °2θ, and 17.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM glycolate Form 1 is DOM glycolate Form 1 characterized by XRPD signals at 5.1 °2θ, 15.1 °2θ, 20.2 °2θ, 25.3 °2θ, 10.1 °2θ, 22.6 °2θ, 14.2 °2θ, 18.1 °2θ, 24.3 °2θ, and 17.8 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM glycolate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, or twenty-five XRPD signals selected from those set forth in Table 12.

Table 12, XRPD Signals for DOM glycolate Form 1

Solid forms of DOM hydrochloride

In some embodiments, the present disclosure provides solid forms of DOM hydrochloride, e.g., crystalline forms of DOM hydrochloride. In some embodiments, the DOM hydrochloride XRPD profile is substantially similar to that shown in FIG. 9. In some embodiments, the DOM hydrochloride ¹H NMR spectrum is substantially similar to that shown in FIG. 38. In some embodiments, the DOM hydrochloride TGA profile is substantially similar to that shown in FIG. 39. In some embodiments, the DOM hydrochloride DSC profile is substantially similar to that shown in FIG. 39.

In some embodiments, the solid form of DOM hydrochloride is crystalline DOM hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2θ, 13.3 °2θ, and 14.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation). In some embodiments, the solid form of DOM hy drochloride is crystalline DOM hydrochloride characterized by XRPD signals at 8.9 °2θ, 13.3 °2θ, and 14.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM hydrochloride is crystalline DOM hydrochloride characterized by two or more, or three or more XRI’D signals selected from the group consisting of 8.9 °2θ, 13.3 °2θ, 14.4 °2θ, 15.9 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM hydrochloride is crystalline DOM hydrochloride characterized by XRPD signals at 8.9 °2θ, 13.3 °2θ, 14/4 °2θ, 15,9 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM hydrochloride is crystalline DOM hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 8,9 °2θ, 26.7 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM hydrochloride is crystalline DOM hydrochloride characterized by XRPD signals at 8.9 °2θ, 26.7 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM hydrochloride is crystalline DOM hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2θ, 26.7 °2θ, 15.9 °2θ, 22.8 °2θ, and 25.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM hydrochloride is DOM hydrochloride characterized by XRPD signals at 8.9 °2θ, 26.7 °2θ, 15.9 °2θ, 22.8 °2θ, and 25.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM hy drochloride is crystalline DOM hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2θ, 26.7 °2θ, 15.9 °2θ, 22.8 °2θ, 25.2 °2θ, 16.7 °2θ, and 17.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM hydrochloride is DOM hydrochloride characterized by XRPD signals at 8.9 °2θ, 26.7 °2θ, 15.9 °2θ, 22.8 °2θ, 25.2 °2θ, 16.7 °2θ, and 17.7 °2θ (±0.2 °2θ; ±0.1 °2θ: or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM hydrochloride is crystalline DOM hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2θ, 26.7 °2θ, 15.9 °2θ, 22.8 °2θ, 25.2 °2θ, 16.7 °2θ, 17.7 °2θ, 27.0 °2θ, 25.9 °2θ, and 30.9 °2θ (±0.2 °2θ. ±0.1 °2θ: or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM hydrochloride is DOM hydrochloride characterized by XRPD signals at 8.9 °2θ, 26.7 °2θ, 15.9 °2θ, 22.8 °2θ, 25.2 °2θ, 16.7 °2θ, 17.7 °2θ, 27.0 °2θ, 25.9 °2θ, and 30.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM hydrochloride is characterized, by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, thirty-six, or thirty-seven XRPD signals selected from those set forth in Table 13.

Table 13. XRPD Signals for DOM hydrochloride

Solid forms of DOM l-hydroxy-2-naphthoate (xinafoate)

In some embodiments, the present disclosure provides solid forms of DOM l -hydroxy-2- naphthoate (xinafoate), e.g., crystal line forms of DOM 1 -hydroxy-2-naphthoate. In some embodiments, the DOM 1 -hydroxy-2-naphthoate XRPD profile is substantially similar to that shown in FIG. 10. In some embodiments, the DOM 1 -hydroxy-2-naphthoate ¹H NMR spectrum is substantially similar to that shown in FIG. 60. In some embodiments, the DOM 1 -hydroxy-2- naphthoate TGA profile is substantially similar to that shown in FIG. 61 . In some embodiments, the DOM l-hydroxy-2-naphthoate DSC profile is substantially similar to that shown in FIG. 61 .

In some embodiments, the solid form of DOM l-hydroxy-2-naphthoate is crystalline DOM l-hydroxy-2-naphthoate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2θ, 10.0 °2θ, and 16.6 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kai radiation). In some embodiments, the solid form of DOM 1 -hydroxy-2-naphthoate is crystalline DOM 1 -hydroxy-2-naphthoate characterized by XRPD signals at 5.0 °2θ, 10.0 °2θ, and 16.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM 1 -hydroxy -2-naphthoate is crystalline DOM 1 -hydroxy -2-naphthoate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2θ, 10.0 °2θ, 16.6 °2θ, 18.1 °2θ, and 24.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM l-hydroxy-2- naphthoate is crystalline DOM 1 -hydroxy-2-naphthoate characterized by XRPD signals at 5.0 °2θ, 10.0 °2θ, 16.6 °2θ, 18.1 °2θ. and 24.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM 1 -hydroxy -2-naphthoate is crystalline DOM 1 -hydroxy -2-naphthoate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.0 °2θ, 16.6 °2θ, and 24.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kai radiation). In some embodiments, the solid form of DOM 1 -hydroxy-2-naphthoate is crystalline DOM l-hydroxy-2-naphthoate characterized by XRPD signals at 10.0 °2θ, 16.6 °2θ, and 24.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM 1 -hydroxy-2-naphthoate is crystalline DOM l-hydroxy-2-naphthoate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 10.0 °2θ, 16.6 °2θ, 24.4 °2θ, 18.1 °2θ, and 21.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM l-hydroxy-2- naphthoate is DOM l-hydroxy-2-naphthoate characterized by XRPD signals at 10.0 °2θ, 16.6 °2θ,

24.4 °2θ, 18.1 °2θ, and 21.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM l-hydroxy-2-naphthoate is crystalline DOM 1 -hydroxy -2-naphthoate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.0 °2θ, 16.6 °2θ, 24,4 °2θ, 18.1 °2θ, 21.5 °2θ, 5.0 °2θ, and 26.4- °2θ (±0,2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM l-hydroxy-2-naphthoate is DOM l-hydroxy-2-naphthoate characterized by XRPD signals at 10.0 °2θ, 16.6 °2θ, 24.4 °2θ, 18.1 °2θ, 21.5 °2θ, 5.0 °2θ, and 26.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM 1 -hydroxy -2-naphthoate is crystalline DOM 1 -hydroxy -2-naphthoate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.0 °2θ, 16.6 °2θ, 24.4 °2θ, 18.1 °2θ, 21.5 °2θ, 5.0 °2θ, 26.4 °2θ,

23.4 °2θ, 25. 1 °2θ, and 18.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM l-hydroxy-2-naphthoate is DOM l-hydroxy-2-naphthoate characterized by XRPD signals at 10.0 °2θ, 16.6 °2θ, 24.4 °2θ, 18.1 °2θ, 21.5 °2θ, 5.0 °2θ, 26.4 °2θ. 23.4 °2θ. 25.1 °2θ, and 18.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

In some embodiments, the crystalline DOM l-hydroxy-2-naphthoate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty- one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, or fifty-one XRPD signals selected from those set forth in Table 14.

Table 14. XRPD Signals for DOM l-hydroxy-2-naphthoate (xinafoate)

29 27.2 3.3 4.4

30 28.0 3.2 4.0

31 29.2 3.1 5.6

32 30.1 3.0 10.7

33 30.4 2.9 3.9

34 31.1 2.9 7.8

35 31.7 2.8 3.2

36 31.9 2.8 3.9

37 32.3 2.8 5.1

38 32.6 2.7 7.4

39 32.9 2.7 4.8

40 33.3 2.7 3.5

41 33.6 2.7 4.5

42 34.0 2.6 3.1

43 34.5 2.6 6.8

44 35.4 2.5 3.7

45 36.4 2.5 4.1

46 36.7 2.5 4.2

47 36.9 2.4 7.7

48 37.6 2.4 5.1

49 38.6 2.3 4.9

50 39.0 2.3 4.3

51 39.2 2.3 5.1

Solid forms of DOM maleate Form 1

In some embodiments, the present disclosure provides solid forms of DOM maleate Form

1 , e.g., crystalline forms of DOM maleate Form 1 . In some embodiments, the DOM maleate Form 1 XRPD profile is substantially similar to that shown in FIG. 65. In some embodiments, the DOM maleate Form 1 NMR spectrum is substantially similar to that shown in FIG. 44. In some embodiments, the DOM maleate Form 1 TGA profile is substantially similar to that shown in FIG. 45. In some embodiments, the DOM maleate Form 1 DSC profile is substantially similar to that shown in FIG. 45.

In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.7 °2θ, 11.5 °2θ, and 14.0 °2θ (+0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by XRPD signals at 4.7 °2θ, 11.5 °2θ, and 14.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.7 °2θ, 11.5 °2θ, 14.0 °2θ, 16.4 °2θ, and 18.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by XRPD signals at 4.7 °2θ, 11.5 °2θ, 14.0 °2θ, 16.4 °2θ, and 18.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by two or more, or three or more XR PD signals selected from the group consisting of 18.7 °2θ, 14.0 °2θ, and 22.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by XRPD signals at 18.7 °2θ, 14.0 °2θ, and 22.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.7 °2θ, 14.0 °2θ, 22.8 °2θ, 23.6 °2θ, and. 19.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by XRPD signals at 18.7 °2θ, 14.0 °2θ, 22.8 °2θ, 23.6 °2θ, and 19,9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.7 °2θ, 14.0 °2θ, 22.8 °2θ, 23.6 °2θ, 19.9 °2θ, 25.1 °2θ, and 18.3 °2θ (±0.2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 1 is DOM maleate Form 1 characterized by XRPD signals at 18.7 °2θ, 14.0 °2θ, 22.8 °2θ,

23.6 °2θ, 19.9 °2θ, 25.1 °2θ, and 18.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate Form 1 is crystalline DOM maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.7 °2θ, 14.0 °2θ, 22.8 °2θ, 23.6 °2θ, 19.9 °2θ, 25.1 °2θ, 18.3 °2θ, 16.4 °2θ, 20.4 °2θ, and 22.2 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 1 is DOM maleate Form 1 characterized by XRPD signals at

18.7 °2θ, 14.0 °2θ, 22.8 °2θ, 23.6 °2θ, 19.9 °2θ, 25.1 °2θ, 18.3 °2θ. 16.4 °2θ, 20.4 °2θ, and 22.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the crystalline DOM maleate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, or twenty-eight XRPD signals selected from those set forth in Table 15.

Table 15. XRPD Signals for DOM maleate Form 1

Solid forms of DOM maleate Forms 1 and 2

In some embodiments, the present disclosure provides solid forms of DOM maleate Forms

1 and 2, e.g., crystalline forms of DOM maleate Forms 1 and 2. In some embodiments, the XRPD profile of a mixture of DOM maleate Forms 1 and 2 is substantially similar to that shown in FIG. 12.

In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 11.5 °2θ, and 13.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kai radiation). In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized by XRPD signals at 4.6 °2θ, 11.5 °2θ, and 13.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized, by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 11.5 °2θ, 13.7 °2θ, 14.9 °2θ, and 16.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized, by XRPD signals at 4.6 °2θ,

11.5 °2θ, 13.7 °2θ, 14.9 °2θ, and 16.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.8 °2θ, 23.6 °2θ, and 25.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kai radiation). In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized by XRPD signals at 22.8 °2θ, 23.6 °2θ, and 25. 1 °2θ (±0,2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.8 °2θ, 23.6 °2θ, 25.1 °2θ, 16.4 °2θ, and 22.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate is a. mixture of crystalline DOM maleate Forms 1 and 2 characterized by XRPD signals at 22.8 °2θ,

23.6 °2θ, 25.1 °2θ, 16.4 °2θ, and 22.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.8 °2θ, 23.6 °2θ, 25.1 °2θ, 16.4 °2θ, 22.4 °2θ, 4.6 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized by XRPD signals at 22.8 °2θ, 23.6 °2θ, 25.1 °2θ, 16.4 °2θ, 22.4 °2θ, 4.6 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.8 °2θ, 23.6 °2θ, 25.1 °2θ, 16.4 °2θ, 22.4 °2θ, 4.6 °2θ, 16.7 °2θ, 18.3 °2θ, 26.7 °2θ, and 13.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM' maleate is a mixture of crystalline DOM maleate Forms 1 and 2 characterized by XRPD signals at 22.8 °2θ, 23.6 °2θ, 25.1 °2θ, 16.4 °2θ, 22.4 °2θ, 4.6 °2θ, 16.7 °2θ, 18.3 °2θ, 26.7 °2θ, and 13.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the mixture of crystalline DOM maleate Forms 1 and 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty -two, twenty- three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nme, thirty, thirty- one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, or forty-four XRPD signals selected from those set forth in Table 16,

Table 16. XRPD Signals for a mixture of DOM maleate Forms 1 and 2

Solid forms of DOM maleate Form 2

In some embodiments, the solid form of DOM maleate Form 2 is crystalline DOM maleate Form 2 characterized by two or more, or three or more XRPD signals selected, from the group consisting of 16.7 °2θ, 13.7 °2θ, and 14.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 2 is crystalline DOM maleate Form 2 characterized by XRPD signals at 16.7 °2θ, 13.7 °2θ, and 14.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate Form 2 is crystalline DOM maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7 °2θ, 13.7 °2θ, 14.9 °2θ, 17.1 °2θ, and 17.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 2 is crystalline DOM maleate Form 2 characterized by XRPD signals at 16.7 °2θ, 13.7 °2θ, 14.9 °2θ, 17.1 °2θ, and 17.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

In some embodiments, the solid form of DOM maleate Form 2 is crystalline DOM maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7 °2θ. 13.7 °2θ, 14.9 °2θ, 17.1 °2θ, 17.8 °2θ, and 28.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM maleate Form 2 is crystalline DOM maleate Form 2 characterized by XRPD signals at 16.7 °2θ, 13.7 °2θ, 14.9 °2θ, 17. 1 °2θ, 17.8 °2θ, and 28.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM maleate Form 2 is characterized by one, two, three, four, five, or six XRPD signals selected from those set forth in Table 16A.

Table 16A. XRPD Signals for DOM maleate Form 2

Solid forms of DOM malonate Form 1

In some embodiments, the present disclosure provides solid forms of DOM malonate Form 1, e.g., crystalline forms of DOM malonate Form 1 . In some embodiments, the DOM malonate Form 1 XRPD profile is substantially similar to that shown in FIGs. 13 or 66. In some embodiments, the DOM malonate Form 1 NMR spectrum is substantially similar to that shown in FIG. 46. In some embodiments, the DOM malonate Form 1 TGA profile is substantially similar to that shown in FIG. 47. In some embodiments, the DOM malonate Form 1 DSC profile is substantially similar to that shown in FIG. 47.

In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ. 16.3 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by XRPD signals at 12.6 °2θ, 16.3 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 1 is ay stall ine DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 15.7 °2θ, 16.3 °2θ, 17.2 °2θ, and 21.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by XRPD signals at 12.6 °2θ, 15.7 °2θ, 16.3 °2θ,

17.2 °2θ, and 21.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 25.5 °2θ, and 21.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by XRPD signals at 12.6 °2θ, 25.5 °2θ, and 21.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 25.5 °2θ, 21.2 °2θ, 26.1 °2θ, and 22.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is DOM malonate Form 1 characterized by XRPD signals at 12,6 °2θ, 25.5 °2θ, 21.2 °2θ, 26.1 °2θ, and 22,4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 25.5 °2θ, 21,2 °2θ, 26.1 °2θ, 22.4 °2θ, 16.3 °2θ, and 14.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is DOM malonate Form 1 characterized by XRPD signals at 12.6 °2θ, 25.5 °2θ,

21.2 °2θ, 26.1 °2θ, 22.4 °2θ, 16.3 °2θ, and 14.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 1 is ay stall ine DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 25.5 °2θ, 21.2 °2θ, 26.1 °2θ, 22.4 °2θ, 16.3 °2θ, 14.2 °2θ, 15.2 °2θ, 22.8 °2θ, and 24.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is DOM malonate Form 1 characterized by XRPD signals at 12.6 °2θ, 25.5 °2θ, 21.2 °2θ, 26.1 °2θ, 22.4 °2θ, 16.3 °2θ, 14.2 °2θ, 15.2 °2θ, 22.8 °2θ, and 24.4 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM malonate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, or twenty-one XRPD signals selected from those set forth in Table 17.

Table 17. XRPD Signals for DOM malonate Form 1

In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 15.6 °2θ, 16.3 °2θ, 17.2 °2θ, and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by XRPD signals at 12.6 °2θ, 15.6 °2θ, 16.3 °2θ, 17.2 °2θ, and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.4 °2θ, 16.3 °2θ, and 4.2 °2θ (±0.2 °2θ; ±0.1 °2θ, or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form I is crystalline DOM malonate Form 1 characterized by XRPD signals at 22.4 °2θ, 16.3 °2θ, and 4.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.4 °2θ, 16.3 °2θ, 4.2 °2θ, 26.1 °2θ, and 26.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is DOM malonate Form 1 characterized by XRPD signals at 22.4 °2θ, 16.3 °2θ, 4.2 °2θ, 26.1 °2θ, and 26.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.4 °2θ, 16.3 °2θ, 4.2 °2θ, 26.1 °2θ, 26.0 °2θ, 4.7 °2θ, and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is DOM malonate Form 1 characterized by XRPD signals at 22.4 °2θ, 16.3 °2θ, 4.2 °2θ, 26.1 °2θ, 26.0 °2θ, 4.7 °2θ, and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 1 is crystalline DOM malonate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.4 °2θ, 16.3 °2θ, 4.2 °2θ, 26.1 °2θ, 26.0 °2θ, 4.7 °2θ, 21.1 °2θ, 22,7 °2θ, 25.4 °2θ, and 15.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 1 is DOM malonate Form 1 characterized by XRPD signals at 22.4 °2θ, 16.3 °2θ, 4.2 °2θ, 26.1 °2θ, 26.0 °2θ, 4.7 °2θ, 21.1 °2θ, 22.7 °2θ, 25.4 °2θ, and 15.2 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM malonate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, or forty-four XRPD signals selected from those set forth in Table 18.

Table 18. XRPD Signals for DOM malonate Form 1 ”77™

33

34

35

36

37

Solid forms of DOM malonate Form 2

In some embodiments, the present disclosure provides solid forms of DOM malonate Form 2, e.g., crystalline forms of DOM malonate Form 2. In some embodiments, the DOM malonate Form 2 XRPD profile is substantially similar to that shown in FIG. 67.

In some embodiments, the solid form of DOM malonate Form 2 is crystalline DOM malonate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 11.8 °2θ, and 13.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 2 is crystalline DOM malonate Form 2 characterized by XRPD signals at 6.0 °2θ, 11.8 °2θ, and 13.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 2 is crystalline DOM malonate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6,0 °2θ, 1 1.8 °2θ, 13.4 °2θ, 15.8 °2θ, and 16.5 °2θ (±0,2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 2 is crystalline DOM malonate Form 2 characterized by XRPD signals at 6.0 °2θ, 11.8 °2θ, 13.4 °2θ, 15.8 °2θ, and 16,5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 2 is crystalline DOM malonate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 15.8 °2θ, and 18.8 °2θ (±0.2 °2θ; ±0.1 °2θ, or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 2 is crystalline DOM malonate Form 2 characterized by XRPD signals at 6.0 °2θ, 15.8 °2θ, and 18.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 2 is crystalline DOM malonate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 15.8 °2θ, 18.8 °2θ, 16.5 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 2 is DOM malonate Form 2 characterized by XRPD signals at 6.0 °2θ, 15.8 °2θ, 18.8 °2θ, 16.5 °2θ, and 22.0 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 2 is crystalline DOM malonate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 15.8 °2θ, 18.8 °2θ, 16.5 °2θ, 22.0 °2θ, 13.4 °2θ, and 22.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 2 is DOM malonate Form 2 characterized by XRPD signals at 6.0 °2θ, 15.8 °2θ, 18.8 °2θ, 16.5 °2θ, 22.0 °2θ, 13.4 °2θ, and 22.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or .0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM malonate Form 2 is crystalline DOM malonate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 15.8 °2θ, 18.8 °2θ, 16.5 °2θ, 22.0 °2θ, 13.4 °2θ, 22.7 °2θ, 24.7 °2θ, 20.1 °2θ, and. 23.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM malonate Form 2 is DOM malonate Form 2 characterized by XRPD signals at 6.0 °2θ, 15.8 °2θ, 18.8 °2θ, 16.5 °2θ, 22.0 °2θ, 13.4 °2θ, 22.7 °2θ, 24.7 °2θ, 20.1 °2θ, and 23.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM malonate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty⁷, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, or thirty-six XRPD signals selected from those set forth in Table 19.

Table 19. XRPD Signals for DOM malonate Form 2

Solid forms of DOM mesylate

In some embodiments, the present disclosure provides solid, forms of DOM mesylate, e.g., crystalline forms of DOM mesylate. In some embodiments, the DOM mesylate XRPD profile is substantially similar to that shown in FIG. 14.

In some embodiments, the solid form of DOM mesylate is crystalline DOM mesylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.9 °2θ, 16.3 °2θ, and 17.0 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mesylate is crystalline DOM mesylate characterized by XRPD signals at 12.9 °2θ, 16.3 °2θ, and 17.0 °2θ (±0,2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mesylate is crystalline DOM mesylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.9 20. 14.9 °2θ, 16.3 °2θ, 17.0 °2θ. and 22.6 °2θ (±0.2 20: ±0.1 20: or ±0.0 °2θ, Cu Kα1 radiation). In some embodiments, the solid form of DOM mesylate is crystalline DOM mesylate characterized by XRPD signals at 12.9 °2θ, 14.9 °2θ, 16.3 °2θ, 17.0 °2θ, and 22.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

In some embodiments, the solid form of DOM mesylate is crystalline DOM mesy late characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.0 °2θ, 16.3 °2θ, and 4. 1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mesylate is crystalline DOM mesylate characterized, by XRPD signals at 17.0 °2θ, 16.3 °2θ, and 4.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM mesylate is crystalline DOM mesylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.0 °2θ, 16.3 °2θ, 4.1 °2θ, 3.9 °2θ, and 24.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 29; Cu Kα1 radiation). In some embodiments, the solid form of DOM mesylate is DOM mesylate characterized by XRPD signals at 17.0 °2θ, 16.3 °2θ, 4.1 °2θ, 3.9 °2θ, and 24.0 °2θ (±0.2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM mesylate is crystalline DOM mesylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.0 °2θ, 16.3 °2θ, 4. 1 °2θ, 3.9 °2θ, 24,0 °2θ, 23/1 °2θ, and 25.5 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mesylate is DOM mesylate characterized by XRPD signals at 17.0 °2θ, 16.3 °2θ, 4.1 °2θ, 3.9 °2θ, 24.0 °2θ, 23.4 °2θ, and 25.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 ^: 29. Cu Kα1 radiation).

In some embodiments, the solid form of DOM mesylate is crystalline DOM mesylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.0 °2θ, 16.3 °2θ, 4.1 °2θ, 3.9 °2θ, 24.0 °2θ, 23.4 °2θ, 25.5 °2θ, 22.6 °2θ, 22.0 °2θ, and 21.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mesylate is DOM mesylate characterized by XRPD signals at 17.0 °2θ, 16.3 °2θ, 4.1 °2θ, 3.9 °2θ, 24.0 °2θ, 23.4 °2θ, 25.5 °2θ, 22.6 °2θ, 22.0 °2θ, and 21.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the crystalline DOM mesylate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, or forty-four XRPD signals selected from those set forth in Table 20.

Table 20, XRPD Signals for DOM mesylate

Solid forms of DOM mucate

In some embodiments, the present disclosure provides solid forms of DOM mucate, e.g., crystalline forms of DOM mucate. In some embodiments, the DOM mucate XRPD profile is substantially similar to that shown in FIG. 21. In some embodiments, the DOM mucate ¹H NMR spectrum is substantially similar to that shown in FIG. 48. In some embodiments, the DOM mucate TGA profile is substantially similar to that shown in FIG. 49. In some embodiments, the DOM mucate DSC profile is substantially similar to that shown in FIG. 49.

In some embodiments, the solid form of DOM mucate is crystalline DOM mucate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 9.2 °2θ, and 13.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mucate is crystalline DOM mucate characterized, by XRPD signals at 4.6 °2θ, 9.2 °2θ, and 13.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM mucate is crystalline DOM mucate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 9.2 °2θ, 13.2 °2θ, 13,8 °2θ, and 16.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mucate is crystalline DOM mucate characterized by XRPD signals at 4.6 °2θ, 9.2 °2θ, 13.2 °2θ, 13.8 °2θ, and 16. 1 °2θ (±0,2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM mucate is crystalline DOM mucate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 13.8 °2θ, 9.2 °2θ, 25.4 °2θ, and 16.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mucate is DOM mucate characterized by XRPD signals at 4.6 °2θ, 13.8 °2θ, 9.2 °2θ, 25.4 °2θ, and 16.6 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM mucate is crystalline DOM mucate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 13.8 °2θ, 9.2 °2θ, 25.4 °2θ, 16.6 °2θ, 18.1 °2θ, and 21.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mucate is DOM mucate characterized by XRPD signals at 4.6 °2θ, 13.8 °2θ, 9.2 °2θ, 25.4 °2θ, 16.6 °2θ, 18.1 °2θ, and 21.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM mucate is crystalline DOM mucate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 13.8 °2θ, 9.2 °2θ, 25.4 °2θ, 16.6 °2θ, 18.1 °2θ, 21.0 °2θ, 16.1 °2θ, 13.2 °2θ, and 23.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM mucate is DOM mucate characterized by XRPD signals at 4.6 °2θ, 13.8 °2θ, 9.2 °2θ, 25.4 °2θ, 16.6 °2θ, 18.1 °2θ, 21.0 °2θ, 16.1 °2θ, 13.2 °2θ, and 23.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM mucate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, or twenty-eight XRPD signals selected from those set forth in Table 21.

Table 21, XRPD Signals for DOM mucate

Solid forms of DOM phosphate

In some embodiments, the present disclosure provides solid forms of DOM phosphate, e.g., crystalline forms of DOM phosphate. In some embodiments, the DOM phosphate XRPD profile is substantially similar to that shown in FIGs. 16 or 68, In some embodiments, the DOM phosphate NMR spectrum is substantially similar to that shown in FIG. 50, In some embodiments, the DOM phosphate TGA profile is substantially similar to that shown in FIG. 51. In some embodiments, the DOM phosphate DSC profile is substantially similar to that shown in FIG. 51.

In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 8.1 °2θ, and 12.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by XRPD signals at 4.1 °2θ. 8.1 °2θ, and 12.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 8.1 °2θ. 12.2 °2θ, 16.7 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ. Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by XRPD signals at 4.1 °2θ, 8.1 °2θ, 12.2 °2θ, 16.7 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 12.2 °2θ, and 24.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by XRPD signals at 4.1 °2θ, 12.2 °2θ, and 24.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 12.2 °2θ, 24.5 °2θ, 16.7 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is DOM phosphate characterized by XRPD signals at 4.1 °2θ, 12.2 °2θ, 24.5 °2θ, 16.7 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 12.2 °2θ, 24.5 °2θ, 16.7 °2θ, 22.0 °2θ, 23.0 °2θ, and 25.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is DOM phosphate characterized by XRPD signals at 4.1 °2θ, 12,2 °2θ, 24.5 °2θ, 16.7 °2θ, 22,0 °2θ, 23.0 °2θ, and 25/4 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 12.2 °2θ, 24.5 °2θ, 16.7 °2θ, 22.0 °2θ, 23.0 °2θ, 25.4 °2θ, 21.5 °2θ, 8.1 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is DOM phosphate characterized by XRPD signals at 4.1 °2θ, 12.2 °2θ, 24.5 °2θ, 16.7 °2θ, 22.0 °2θ, 23.0 °2θ, 25.4 °2θ, 21.5 °2θ, 8.1 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM phosphate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, or twenty-seven XRPD signals selected from those set forth in Table 22. Table 22. XRPD Signals for DOM phosphate

Signal no. Position d-value Relative

1 4.1 21.4 100.0

2 8.1 10.9 11.1

3 12.2 7.2 34.7

4 13.7 6.5 1.9

5 15.1 5.9 4.5

6 15.4 5.8 2.9

7 15.9 5.6 3.6

8 16.7 5.3 19.9

9 20.8 4.3 4.5

10 21.5 4.1 11.2

11 22.0 4.0 19.3

12 23.0 3.9 12.3

13 23.5 3.8 3.0

14 24.5 3.6 24.5

15 25.4 3.5 11.8

16 26.3 3.4 4.0

17 26.9 3.3 2.6

18 27.6 3.2 2.5

19 29.8 3.0 1.8

20 30.8 2.9 2.5

21 32.1 2.8 1.6

22 32.8 2.7 3.3

23 33.7 2.7 1.2

24 34.6 2.6 1.2

25 35.7 2.5 2.6

26 37.1 2.4 1.9

27 38.6 2.3 2.1

In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 16.7 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by XRPD signals at 4.1 °2θ, 16.7 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM phosphate is cry stalline DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 16.7 °2θ, 22.0 °2θ, 24.6 °2θ, and 12.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is DOM phosphate characterized by XRPD signals at 4.1 °2θ, 16.7 °2θ, 22.0 °2θ, 24.6 °2θ, and 12.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM phosphate is cry stalline DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 16.7 °2θ, 22.0 °2θ, 24.6 °2θ, 12.2 °2θ, 23.0 °2θ, and 25.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is DOM phosphate characterized by XRPD signals at 4.1 °2θ, 16.7 °2θ, 22.0 °2θ, 24.6 °2θ, 12.2 °2θ, 23.0 °2θ, and 25.4 °2θ (.±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM phosphate is crystalline DOM phosphate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 4.1 °2θ, 16.7 °2θ, 22.0 °2θ, 24.6 °2θ, 12.2 °2θ, 23.0 °2θ, 25.4 °2θ, 21.5 °2θ, 20.8 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM phosphate is DOM phosphate characterized by XRPD signals at 4.1 °2θ, 16.7 °2θ, 22.0 °2θ, 24.6 °2θ, 12.2 °2θ, 23.0 °2θ, 25.4 °2θ, 21.5 °2θ, 20.8 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 26: or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM phosphate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, or forty XRPD signals selected from those set forth in Table 23.

Table 23. XRPD Signals for DOM phosphate

Solid forms of DOM sulfate

In some embodiments, the present disclosure provides solid forms of DOM sulfate, e.g., crystalline forms of DOM sulfate. In some embodiments, the DOM sulfate XRPD profile is substantially similar to that shown in FIGs. 17 or 69. In some embodiments, the DOM sulfate ¹H NMR spectrum is substantially similar to that shown in FIG. 54. In some embodiments, the DOM sulfate TGA profile is substantially similar to that shown in FIG. 55. In some embodiments, the DOM sulfate DSC profile is substantially similar to that shown in FIG. 55. In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.2 °2θ, 13.8 °2θ, and 20.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by XRPD signals at 11.2 °2θ, 13.8 °2θ, and 20.4 °2θ (.±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.2 °2θ, 13.8 °2θ, 17.3 °2θ, 20.4 °2θ, and 20.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is cry stalline DOM sulfate characterized by XRPD signals at 11.2 °2θ, 13.8 °2θ, 17.3 °2θ, 20.4 °2θ, and 20.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 20.4 °2θ, 13.8 °2θ, and 20.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by XRPD signals at 20,4 °2θ, 13.8 °2θ, and 20.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.4 °2θ, 13.8 °2θ, 20.8 °2θ, 24/4 °2θ, and 25.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is DOM sulfate characterized by XRPD signals at 20.4 °2θ, 13.8 °2θ, 20.8 °2θ, 24.4 °2θ, and 25. 1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.4 °2θ, 13.8 °2θ, 20.8 °2θ, 24.4 °2θ, 25.1 °2θ, 1 1.2 °2θ, and 24.1 °2θ (±0.2 °2θ, ±0.1 °2θ, or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is DOM sulfate characterized by XRPD signals at 20.4 °2θ, 13.8 °2θ, 20.8 °2θ, 24.4 °2θ, 25. 1 °2θ, 11.2 °2θ, and 24.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.4 °2θ, 13.8 °2θ, 20.8 °2θ, 24.4 °2θ, 25.1 °2θ, 11.2 °2θ, 24.1 °2θ, 20.2 °2θ, 17.3 °2θ, and 23.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is DOM sulfate characterized by XRPD signals at 20.4 °2θ, 13.8 °2θ, 20.8 °2θ, 24.4 °2θ, 25.1 °2θ, 11.2 °2θ, 24. 1 20. 20 2 ^;°2θ. 1'7.3 °2θ, and 23.3 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM sulfate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, or thirty-one XRPD signals selected from those set forth in Table 24.

Table 24, XRPD Signals for DOM sulfate

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 13.6 °2θ, and 14.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by XRPD signals at 5.1 °2θ, 13,6 °2θ, and 14.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 10.4 °2θ, 13.6 °2θ, 14.7 °2θ, and 20.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by XRPD signals at 5.1 °2θ, 10.4 °2θ, 13.6 °2θ, 14.7 °2θ, and 20.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.4 °2θ, 24.4 °2θ, and 14.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by XRPD signals at 20.4 °2θ, 24.4 °2θ, and 14.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.4 °2θ, 24.4 °2θ, 14.7 °2θ, 5.1 °2θ, and 13.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is DOM sulfate characterized by XRPD signals at 20.4 °2θ, 24.4 °2θ, 14.7 °2θ, 5.1 °2θ, and 13.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 20.4 °2θ, 24.4 °2θ, 14.7 °2θ, 5.1 °2θ, 13.6 °2θ, 25.1 °2θ, and 10.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is DOM sulfate characterized by XRPD signals at 20.4 °2θ, 24.4 °2θ, 14.7 °2θ, 5.1 °2θ, 13.6 °2θ, 25.1 °2θ, and. 10.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is crystalline DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.4 °2θ, 24.4 °2θ, 14.7 °2θ, 5.1 °2θ, 13.6 °2θ, 25.1 °2θ, 10.4 °2θ, 17.1 °2θ, 20.8 °2θ, and 23.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM sulfate is DOM sulfate characterized by XRPD signals at 20.4 °2θ, 24.4 °2θ, 14.7 °2θ, 5.1 °2θ, 13.6 °2θ, 25.1 °2θ, 10.4 °2θ, 17.1 °2θ, 20.8 °2θ, and 23.5 °2θ (±0.2 °2θ: ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM sulfate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, or forty XRPD signals selected from those set forth in Table 25.

Table 25. XRPD Signals for DOM sulfate

Solid forms of DOM succinate

In some embodiments, the present disclosure provides solid forms of DOM succinate, e.g., crystalline forms of DOM succinate. In some embodiments, the DOM succinate XRPD profile is substantially similar to that shown in FIG. 18. In some embodiments, the DOM succinate ¹H NMR spectrum is substantially similar to that shown in FIG. 52. In some embodiments, the DOM succinate TGA profile is substantially similar to that shown in FIG. 53. In some embodiments, the DOM succinate DSC profile is substantially similar to that shown in FIG. 53.

In some embodiments, the solid form of DOM succinate is crystalline DOM succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.8 °2θ, 9.6 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM succinate is crystalline DOM succinate characterized by XRPD signals at 4.8 °2θ, 9.6 26. and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

In some embodiments, the solid form of DOM succinate is crystalline DOM succinate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 4.8 °2θ, 9.6 °2θ, 10.6 °2θ, 14.4 °2θ, and 19.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM succinate is crystalline DOM succinate characterized by XRPD signals at 4.8 °2θ, 9.6 °2θ, 10.6 °2θ, 14.4 °2θ, and 19.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM succinate is crystalline DOM succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2θ, 4.8 °2θ, and 14.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM succinate is crystalline DOM succinate characterized by XRPD signals at 9.6 °2θ. 4.8 °2θ, and 14.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM succinate is crystalline DOM succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2θ, 4.8 °2θ, 14.4 °2θ, 19.2 °2θ, and 21.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM succinate is DOM succinate characterized by XRPD signals at 9.6 °2θ, 4.8 °2θ, 14.4 °2θ, 19.2 °2θ, and 21.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM succinate is crystalline DOM succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2θ, 4.8 °2θ, 14.4 °2θ, 19.2 °2θ, 21.4 °2θ, 25.0 °2θ, and 24.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM succinate is DOM succinate characterized by XRPD signals at 9.6 °2θ, 4.8 °2θ, 14.4 °2θ, 19.2 °2θ, 21,4 °2θ, 25.0 °2θ, and 24.0 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM succinate is crystalline DOM succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2θ, 4.8 °2θ, 14.4 °2θ, 19.2 °2θ, 21.4 °2θ, 25.0 °2θ, 24.0 °2θ, 10.6 °2θ, 27.7 °2θ, and 18.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM succinate is DOM succinate characterized by XRPD signals at 9.6 °2θ, 4.8 °2θ, 14.4 °2θ, 19.2 °2θ, 21.4 °2θ, 25.0 °2θ, 24.0 °2θ, 10.6 °2θ, 27.7 °2θ, and 18.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM succinate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, or twenty-five XRPD signals selected from those set forth in Table 26. Table 26. XRPD Signals for DOM succinate

Solid forms of DOM L-tartrate Form 1

In some embodiments, the present disclosure provides solid, forms of DOM L-tartrate, e.g., crystalline forms of DOM L-tartrate Form 1. In some embodiments, the DOM L-tartrate Form 1 XRPD profile is substantially similar to that shown in FIGs. 19 or 70, In some embodiments, the DOM L-tartrate Form 1 ¹H NMR spectrum is substantially similar to that shown in FIG. 56. In some embodiments, the DOM L-tartrate Form 1 TGA profile is substantially similar to that shown in FIG, 57. In some embodiments, the DOM L-tartrate DSC Form 1 profile is substantially similar to that shown in FIG. 57.

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 10.6 °2θ, and 12.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by XRPD signals at 6.1 °2θ, 10.6 °2θ, and 12.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 10.6 °2θ, 12.2 °2θ, 18.4 °2θ, and 20.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L-tartrate Form 1 characterized by XRPD signals at 6.1 °2θ, 10.6 °2θ, 12.2 °2θ, 18.4 °2θ, and. 20.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.2 °2θ, 18.4 °2θ, and 13.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L~ tartrate Form 1 characterized by XRPD signals at 12.2 °2θ, 18.4 °2θ, and 13.7 °2θ (±0.2. °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.2 °2θ, 18.4 °2θ, 13.7 °2θ, 21.0 °2θ, and 13.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is DOM L-tartrate Form 1 characterized by XRPD signals at 12.2 °2θ, 18.4 °2θ, .13.7 °2θ, 21.0 °2θ, and 13,5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- ta.rt.rate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.2 °2θ, 18.4 °2θ, 13.7 °2θ, 21.0 °2θ, 13.5 °2θ, 20.2 °2θ, and 23.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L- tartrate Form 1 is DOM L-tartrate Form 1 characterized by XRPD signals at 1.2.2 °2θ, 18.4 °2θ, 13.7 °2θ, 21.0 °2θ, 13.5 °2θ, 20.2 °2θ, and 23.9 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.2 °2θ, 18.4 °2θ, 13.7 °2θ, 21.0 °2θ, 13.5 °2θ, 20.2 °2θ, 23.9 °2θ, 6.1 °2θ, 27.2 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is DOM L-tartrate Form 1 characterized by XRPD signals at 12.2 °2θ, 18.4 °2θ, 13.7 °2θ, 21.0 °2θ, 13.5 °2θ, 20.2 °2θ, 23.9 °2θ, 6.1 °2θ, 27.2 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM L-tartrate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, or thirty-four XRPD signals selected from those set forth in Table 27.

Table 27. XRPD Signals for DOM L-tartrate Form 1

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 12.1 °2θ, and 18.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L~ tartrate Form 1 characterized by XRPD signals at 6.0 °2θ, 12.1 °2θ, and 18.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 12.1 °2θ, 13.6 °2θ, 18.2 °2θ, and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L-tartrate Form 1 characterized by XRPD signals at 6.0 °2θ, 12, 1 °2θ, 13.6 °2θ, 18.2 °2θ, and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- ta.rt.rate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12. 1 °2θ, 18.2 °2θ, and 13.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by XRPD signals at 12.1 °2θ, 18.2 °2θ, and 13.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12. 1 °2θ, 18.2 °2θ, 13.6 °2θ, 21.1 °2θ, and 20.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is DOM L-tartrate Form 1 characterized by XRPD signals at 12.1 °2θ. 18.2 °2θ, 13.6 °2θ, 21.1 °2θ, and 20.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2θ, 18.2 °2θ, 13.6 °2θ, 21.1 °2θ, 20.2 °2θ, 6.0 °2θ, and 23.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L- tartrate Form 1 is DOM L-tartrate Form 1 characterized by XRPD signals at 12.1 °2θ, 18.2 °2θ, 13.6 °2θ, 21. 1 °2θ, 20.2 °2θ, 6.0 °2θ, and 23.6 °2θ (±0.2 °2θ: ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-tartrate Form 1 is crystalline DOM L- tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2θ, 18.2 °2θ, 13.6 °2θ, 21.1 °2θ, 20.2 °2θ, 6.0 °2θ, 23.6 °2θ, 2.7.2 °2θ, 29.3 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-tartrate Form 1 is DOM L-tartrate Form 1 characterized by XRPD signals at 12.1 °2θ, 18.2 °2θ, 13.6 °2θ, 21.1 °2θ, 2.0.2 °2θ, 6.0 °2θ, 23.6 °2θ, 27.2 °2θ, 29.3 °2θ, and. 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM L-tartrate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty’, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, or twenty-eight XRPD signals selected from those set forth in Table 28.

Table 28. XRPD Signals for DOM L-tartrate Form 1

Solid forms of DOM tosylate Form 1

In some embodiments, the present disclosure provides solid, forms of DOM tosylate Form 1, e.g., crystalline forms of DOM tosylate Form 1. In some embodiments, the DOM tosylate Form 1 XRPD profile is substantially similar to that shown in FIG. 20. In some embodiments, the DOM tosylate Form 1 ^lH NMR spectrum is substantially similar to that shown in FIG. 58. In some embodiments, the DOM tosylate Form 1 TGA profile is substantially similar to that shown in FIG. 59. In some embodiments, the DOM tosylate Form 1 DSC profile is substantially similar to that shown in FIG, 59,

In some embodiments, the solid form of DOM tosylate Form 1 is crystalline DOM tosylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 7.7 °2θ, and 11.9 °2θ (±0.2 °2θ, ±0. 1 °2θ, or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM tosylate Form 1 is crystalline DOM tosylate Form 1 characterized by XRPD signals at 6.0 °2θ, 7.7 °2θ, and 11.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM tosylate Form 1 is crystalline DOM tosylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 7.7 °2θ, 8.4 °2θ, 10.3 °2θ, and 1 1.9 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±0.0 °2θ; Cu Kai radiation). In some embodiments, the solid form of DOM tosylate Form 1 is cry stalline DOM tosylate Form 1 characterized by XRPD signals at 6.0 °2θ, 7.7 °2θ, 8.4 °2θ, 10.3 °2θ, and 11.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM tosylate Form 1 is crystalline DOM tosylate Form 1 characterized by two or more, or three or more XR PD signals selected from the group consisting of 11.9 °2θ, 6.0 °2θ, 7.7 °2θ. 22.0 ^: 29. and 8.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kai radiation). In some embodiments, the solid form of DOM tosylate Form 1 is DOM tosylate Form 1 characterized by XRPD signals at 11.9 °2θ, 6.0 °2θ, 7.7 °2θ, 22.0 °2θ, and 8.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM tosylate Form 1 is crystalline DOM tosylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.9 °2θ, 6.0 °2θ, 7.7 °2θ, 22.0 °2θ, 8.4 °2θ, 24.7 °2θ, and. 23.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM tosylate Form 1 is DOM tosylate Form 1 characterized by XRPD signals at 11.9 °2θ, 6.0 °2θ, 7.7 °2θ, 22.0 °2θ, 8.4 °2θ, 24.7 °2θ, and 23.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM tosylate Form 1 is crystalline DOM tosylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.9 °2θ, 6.0 °2θ, 7.7 °2θ, 22.0 °2θ, 8.4 °2θ, 24.7 °2θ, 23.4 °2θ, 22.8 °2θ, 21.5 °2θ, and 19,7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM tosylate Form 1 is DOM tosylate Form 1 characterized by XRPD signals at 11,9 °2θ, 6.0 °2θ, 7.7 °2θ, 22.0 °2θ, 8.4 °2θ, 24.7 °2θ, 23.4 °2θ, 22.8 °2θ, 21.5 °2θ, and 19.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM tosylate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, or forty-eight XRPD signals selected from those set forth in Table 29.

Table 29. XRPD Signals for DOM tosyiate Form 1

Solid forms of DOM tosylate Form 2

In some embodiments, the present disclosure provides solid forms of DOM tosylate Form 2, e.g., crystalline forms of DOM tosylate Form 2. In some embodiments, the DOM tosylate Form 2 XRPD profile is substantially similar to that shown in FIG. 71.

In some embodiments, the solid form of DOM tosylate Form 2 is crystalline DOM tosylate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.8 °2θ, 7.9 °2θ, and 11.7 °2θ (±0.2 °2θ, ±0. 1 °2θ, or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM tosylate Form 2 is crystalline DOM tosylate Form 2 characterized by XRPD signals at 5.8 °2θ, 7.9 °2θ, and 11.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM tosylate Form 2 is crystalline DOM tosylate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.8 °2θ. 7.9 °2θ, 11.7 °2θ, 14.2 °2θ, and 22.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM tosylate Form 2 is crystalline DOM tosylate Form 2 characterized by XRPD signals at 5.8 °2θ, 7.9 °2θ, 11.7 °2θ, 14.2 °2θ, and 22.3 °2θ (±0.2 ^: 29: ±0.1 ^: 29: or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM tosylate Form 2 is crystalline DOM tosylate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7 °2θ, 22.3 °2θ, and 5.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM tosylate Form 2 is crystalline DOM tosylate Form 2 characterized by XRPD signals at 11.7 °2θ, 22.3 °2θ, and 5.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM tosylate Form 2 is crystalline DOM tosylate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7 °2θ, 22.3 °2θ, 5.8 °2θ, 7.9 °2θ, and 19.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM tosylate Form 2 is DOM tosylate Form 2 characterized by XRPD signals at 11.7 °2θ, 22.3 °2θ, 5.8 °2θ, 7.9 °2θ, and 19.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM tosylate Form 2 is crystalline DOM tosylate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 1 1.7 °2θ, 22.3 °2θ, 5.8 °2θ, 7.9 °2θ, 19.2 °2θ, 18.6 °2θ, and 23.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM tosylate Form 2 is DOM tosylate Form 2 characterized by XRPD signals at 11.7 °2θ, 22.3 °2θ, 5.8 °2θ, 7.9 °2θ,

19.2 °2θ, 18.6 °2θ, and 23.9 °2θ (±0.2 °2θ; ±0.1 °2θ: or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM tosylate Form 2 is crystalline DOM tosylate Form 2 characterized by two or more, or three or more XR PD signals selected from the group consisting of 11.7 °2θ, 22.3 °2θ, 5.8 °2θ, 7.9 °2θ, 19.2 °2θ, 18.6 °2θ, 23.9 °2θ, 23.6 °2θ, 21.8 °2θ, and 20.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM tosylate Form 2 is DOM tosylate Form 2 characterized by XRPD signals 11.7 °2θ,

22.3 °2θ, 5.8 °2θ, 7.9 °2θ, 19.2 °2θ, 18.6 °2θ, 23.9 °2θ, 23.6 °2θ, 21.8 °2θ, and. 20.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM tosylate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, or thirty-one XRPD signals selected from those set forth in Table 30.

Table 30. XRPD Signals for DOM tosylate Form 2

Solid forms of DOM ethanesulfonate (esylate)

In some embodiments, the present disclosure provides solid forms of DOM ethanesulfonate (esylate), e.g., crystalline forms of DOM ethanesulfonate. In some embodiments, the DOM ethanesulfonate XRPD profile is substantially similar to that shown in FIG. 22. In some embodiments, the DOM ethanesulfonate ¹H NMR spectrum is substantially similar to that shown in FIG, 28. In some embodiments, the DOM ethanesulfonate TGA profile is substantially similar to that shown in FIG. 29. In some embodiments, the DOM ethanesulfonate DSC profile is substantially similar to that shown in FIG. 29.

In some embodiments, the solid form of DOM ethanesulfonate is crystalline DOM ethanesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2θ, 13.0 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ. or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM ethanesulfonate is crystalline DOM ethanesulfonate characterized by XRPD signals at 7.6 °2θ, 13.0 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM ethanesulfonate is crystalline DOM ethanesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2θ, 13.0 °2θ, 15.1 °2θ, 20.0 °2θ, and 22.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM ethanesulfonate is crystalline DOM ethanesulfonate characterized by XRPD signals at 7.6 °2θ, 13.0 °2θ, 15.1 °2θ, 20.0 °2θ, and 22.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

In some embodiments, the solid form of DOM ethanesulfonate is crystalline DOM ethanesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2θ. 22.8 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM ethanesulfonate is crystalline DOM ethanesulfonate characterized by XRPD signals at 7.6 °2θ, 22.8 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM ethanesulfonate is crystalline DOM ethanesulfonate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 7.6 °2θ, 22.8 29. 15.1 °2θ, 13.0 26. 20.0 °2θ, 13.3 °2θ, and 22.0 26 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM ethanesulfonate is DOM ethanesulfonate characterized by XRPD signals at 7.6 °2θ, 22.8 °2θ, 15.1 °2θ, 13.0 °2θ, 20.0 °2θ, 13.3 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM ethanesulfonate is crystalline DOM ethanesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 7,6 °2θ, 22.8 °2θ, 15.1 °2θ, 13.0 °2θ, 20.0 °2θ, 13.3 °2θ, 22.0 °2θ, 19,8 °2θ, 17.1 °2θ, and 9.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM ethanesulfonate is DOM ethanesulfonate characterized by XRPD signals at 7.6 °2θ, 22.8 °2θ, 15.1. °2θ, 13.0 °2θ, 20.0 °2θ, 13.3 °2θ, 22.0 °2θ, 19.8 °2θ, 17.1 °2θ, and 9.9 °2θ (±0,2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM ethanesulfonate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, or twenty-eight XRPD signals selected from those set forth in Table 31 .

Table 31. XRPD Signals for DOM ethanesulfonate (esyiate)

Solid forms of DOM lactate

In some embodiments, the present disclosure provides solid forms of DOM lactate, e.g., crystalline forms of DOM lactate. In some embodiments, the DOM lactate XRPD profile is substantially similar to that shown in FIG. 23. In some embodiments, the DOM lactate *H NMR spectrum is substantially similar to that shown in FIG. 40. In some embodiments, the DOM lactate TGA profile is substantially similar to that shown in FIG. 41. In some embodiments, the DOM lactate DSC profile is substantially similar to that shown in FIG. 41.

In some embodiments, the solid form of DOM lactate is crystalline DOM lactate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.3 °2θ, 12.5 °2θ, and 13.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM lactate is crystalline DOM lactate characterized by XRPD signals at 10.3 °2θ, 12.5 °2θ, and 13.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM lacta te is crystalline DOM lactate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.3 °2θ, 12.5 °2θ, 13.1 °2θ, 14.6 °2θ, and 16.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM lactate is crystalline DOM lactate characterized by XRPD signals at 10.3 °2θ, 12.5 °2θ, 13.1 °2θ, 14.6 °2θ, and 16.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

In some embodiments, the solid form of DOM lactate is crystalline DOM lactate characterized by two or more, or three or more XRPD signals selected from the group consisting of 25.3 °2θ, 21.6 °2θ, and 16.2 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM lactate is crystalline DOM lactate characterized by XRPD signals at 25.3 °2θ, 21.6 °2θ, and 16.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM lactate is crystalline DOM lactate characterized by two or more, or three or more XRPD signals selected, from the group consisting of 25.3 °2θ, 21.6 °2θ, 16.2 °2θ, 13.1 °2θ, and 14.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM lactate is DOM lactate characterized by XRPD signals at 25.3 °2θ, 21.6 °2θ, 1.6.2 °2θ, .13.1 °2θ, and 14.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1. radiation).

In some embodiments, the solid form of DOM lactate is crystalline DOM lactate characterized by two or more, or three or more XRPD signals selected from the group consisting of 25.3 °2θ, 21.6 °2θ, 16.2 °2θ, 13.1 °2θ, 14.6 °2θ, 17.8 °2θ, and 17.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation). In some embodiments, the solid form of DOM lactate is DOM lactate characterized by XRPD signals at 25.3 °2θ, 21.6 °2θ, 16.2 °2θ, 13.1 °2θ, 14.6 °2θ, 17.8 ^: 29. and 17.7 °2θ (±0.2 20: ±0.1 °2θ; or ±0.0 °2θ, Cu Kα1 radiation).

In some embodiments, the solid form of DOM lacta te is crystalline DOM lactate characterized by two or more, or three or more XRPD signals selected from the group consisting of 25.3 °2θ, 21.6 °2θ, 16.2 °2θ, 13.1 °2θ, 14.6 °2θ, 17.8 °2θ, 17.7 °2θ, 12.5 °2θ, 26.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM lactate is DOM lactate characterized by XRPD signals at 25.3 °2θ, 21.6 °2θ, 16.2 °2θ, 13.1 °2θ, 14.6 °2θ, 17.8 °2θ, 17.7 °2θ, 12.5 °2θ, 26.2 °2θ, and 20.3 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM lactate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, or twenty-six XRPD signals selected from those set forth in Table 32,

Table 32. XRPD Signals for DOM lactate

Solid forms of DOM L-malate Form 1

In some embodiments, the present disclosure provides solid forms of DOM L-malate Form

1 , e.g., crystalline forms of DOM L-malate Form 1 . In some embodiments, the DOM L-malate Form 1 XRPD profile is substantially similar to that shown in FIG. 11. In some embodiments, the DOM L-malate Form 1 ¹H NMR spectrum is substantially similar to that shown in FIG. 42. In some embodiments, the DOM L-malate Form 1 TGA profile is substantially similar to that shown in FIG. 43. In some embodiments, the DOM L-malate Form 1 DSC profile is substantially similar to that shown in FIG. 43.

In some embodiments, the solid form of DOM L-malate Form 1 is crystalline DOM L- malate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.2 °2θ, 12.6 °2θ, and 15.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 1 is crystalline DOM L- malate Form 1 characterized, by XRPD signals at 4.2 °2θ, 12.6 °2θ, and. 15.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 1 is crystalline DOM L- malate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.2 °2θ, 12.6 °2θ, 15.2 °2θ, 16.6 °2θ, and 24.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 1 is crystalline DOM L-malate Form 1 characterized by XRPD signals at 4.2 °2θ, 12,6 °2θ, 15.2 °2θ, 16.6 °2θ, and 24.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 1 is crystalline DOM L- malate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 4.2 °2θ, and 16.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 1 is crystalline DOM L- malate Form 1 characterized by XRPD signals at 12.6 °2θ, 4.2 °2θ, and 16.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 1 is crystalline DOM L- malate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 4.2 °2θ, 16.6 °2θ, 24.7 °2θ, and 22.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 1 is DOM L-malate Form 1 characterized by XRPD signals at 12.6 °2θ, 4.2 °2θ, 16.6 °2θ, 24.7 °2θ, and 22.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 1 is cry stalline DOM L- malate Form I characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 4.2 °2θ, 16.6 °2θ, 24.7 °2θ, 22.8 °2θ, 21.5 °2θ, and 23.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L- malate Form 1 is DOM L-malate Form 1 characterized by XRPD signals at 12.6 °2θ, 4.2 °2θ, 16.6 °2θ, 24.7 °2θ, 22.8 °2θ, 21.5 °2θ, and 23.8 °2θ (±0.2 °2θ; ±0.1 °2θ: or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 1 is crystalline DOM L- malate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 4.2 °2θ, 16.6 °2θ, 24.7 °2θ, 22.8 °2θ, 21.5 °2θ, 23.8 °2θ, 15.2 °2θ, 25.9 °2θ, and 25.3 °2θ (±0.2 °2θ. ±0.1 °2θ: or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 1 is DOM L-malate Form 1 characterized by XRPD signals at 12.6 °2θ, 4.2 °2θ, 16.6 °2θ, 24.7 °2θ, 22.8 °2θ, 21.5 °2θ, 23.8 °2θ, 15.2 °2θ, 25.9 °2θ, and 25.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM L-malate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty -two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, or thirty XRPD signals selected from those set forth in Table 33.

Table 33. XRPD Signals for DOM L-malate Form 1

Solid forms of DOM L-malate Forms 1 and 2

In some embodiments, the present disclosure provides solid, forms of DOM L-malate Forms 1 and 2, e.g., crystalline forms of DOM L-malate Forms 1 and 2. In some embodiments, the XRPD profile of a mixture of DOM L-malate Forms 1 and 2 is substantially similar to that shown in FIG. 77.

In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and. 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kai radiation). In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by XRPD signals at 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 13.2 °2θ, 14.4 °2θ, 14,9 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by XRPD signals at 3.9 °2θ, 13.2 °2θ, 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, and 24.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kai radiation). In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by XRPD signals at 3.9 °2θ, 15.9 °2θ, and 24.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 16.6 °2θ, and 21.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by XRPD signals at 3.9 °2θ, 15.9 °2θ, 24.5 20. 16.6 °2θ, and 21.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized, by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 16.6 °2θ, 21.4 °2θ, 22.8 °2θ, and. 4.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by XRPD signals at 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 16.6 °2θ, 21.4 °2θ, 22.8 °2θ, and 4.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 16,6 °2θ, 21 .4 °2θ, 22.8 °2θ, 4. 1 °2θ, 25.8 °2θ, 25.0 °2θ, and 26.1 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate is a mixture of crystalline DOM L-malate Forms 1 and 2 characterized by XRPD signals at 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 16.6 °2θ, 21.4 °2θ, 22.8 °2θ, 4.1 °2θ, 25.8 °2θ, 25.0 °2θ, and 26.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ, Cu Kα1 radiation).

In some embodiments, the mixture of crystalline DOM L-malate Forms 1 and 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty- three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty- one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, or fifty XRPD signals selected from those set forth in Table 34. Table 34. XRPD Signals for a mixture of DOM L-malate Forms 1 and 2

Solid forms of DOM L- malate Form 2

In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L- malate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ. ±0.1 °2θ. or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L-malate Form 2 characterized by XRPD signals at 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ, ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L- malate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 13.2 °2θ, 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L-malate Form 2 characterized by XRPD signals at 3.9 °2θ, 13.2 °2θ, 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L- malate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, and 24.5 °2θ (±0.2 °2θ; ±0.1 °2θ. or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L-malate Form 2 characterized by XRPD signals at 3.9 °2θ, 15.9 °2θ, and 24.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L- malate Form 2 characterized, by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 25.0 °2θ, and 26.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0,0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L-malate Form 2 characterized by XRPD signals at 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 25.0 °2θ, and 26.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L- malate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 25.0 °2θ, 26.1 °2θ, 14.9 °2θ, and 23.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L- malate Form 2 is crystalline DOM L-malate Form 2 characterized by XRPD signals at 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 25.0 °2θ, 26.1 °2θ, 14.9 °2θ, and 23.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L- maiate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 25.0 °2θ, 26.1 °2θ, 14.9 °2θ, 23.3 °2θ, 20.6 °2θ, 15.4 °2θ, and 2O.1°2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 2 is crystalline DOM L-malate Form 2 characterized by XRPD signals at 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 25.0 °2θ, 26.1 °2θ, 14.9 °2θ, 23.3 °2θ, 20.6 °2θ, 15.4 °2θ, and 20.1°2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM L-malate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, or twenty-one XRPD signals selected from those set forth in Table 34A.

Table 34A. XRPD Signals for DOM L-malate Form 2

Solid forms of DOM L-malate Form 3

In some embodiments, the present disclosure provides solid forms of DOM L-malate Form 3, e.g., crystalline forms of DOM L-malate Form 3. In some embodiments, the DOM L-malate Form 3 XRPD profile is substantially similar to that shown in FIG. 78.

In some embodiments, the solid form of DOM L-malate Form 3 is crystalline DOM L- malate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5,9 °2θ, 1 1.8 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 3 is crystalline DOM L- malate Form 3 characterized by XRPD signals at 5.9 °2θ, 1 1.8 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 3 is crystalline DOM L- malate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 4.3 °2θ, 5.9 °2θ, 11.8 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 3 is crystalline DOM L-malate Form 3 characterized by XRPD signals at 3.9 °2θ, 4.3 °2θ, 5.9 °2θ, 11.8 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 3 is cry stalline DOM L- malate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.9 °2θ, 23.7 °2θ, and 11.8 °2θ (±0.2 °2θ; ±0.1 °2θ. or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 3 is crystalline DOM L- malate Form 3 characterized by XRPD signals at 5.9 °2θ, 23.7 °2θ, and 11.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 3 is crystalline DOM L- malate Form 3 characterized, by two or more, or three or more XR PD signals selected from the group consisting of 5.9 °2θ, 23.7 °2θ, 11.8 °2θ, 13.8 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L-malate Form 3 is DOM L-malate Form 3 characterized by XRPD signals at 5.9 °2θ, 23.7 °2θ, 11.8 °2θ, 13.8 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 3 is crystalline DOM L- malate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.9 °2θ, 23.7 °2θ, 11.8 °2θ, 13.8 °2θ, 16.7 °2θ, 24.6 °2θ, and 13.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L- malate Form 3 is DOM L-malate Form 3 characterized by XRPD signals at 5.9 °2θ, 23.7 °2θ, 11.8 °2θ, 13.8 °2θ, 16.7 °2θ, 24.6 °2θ, and 13.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM L-malate Form 3 is crystalline DOM L- malate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.9 °2θ, 23.7 °2θ, 11.8 °2θ, 13.8 °2θ, 16.7 °2θ, 24.6 °2θ, 13.6 °2θ, 4.3 °2θ, 14.2 °2θ, and 3.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM L, -malate Form 3 is DOM L, -malate Form 3 characterized by XRPD signals at 5.9 °2θ, 23.7 °2θ, 11.8 °2θ, 13.8 °2θ, 16.7 °2θ, 24.6 °2θ, 13.6 °2θ, 4.3 °2θ, 14.2 °2θ, and 3.9 °2θ (±0.2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM L, -malate Form 3 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty- three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, or forty-five XRPD signals selected from those set forth in Table 35.

Table 35. XRPD Signals for DOM L-maiate Form 3

Solid forms of DOM Form A.

In some embodiments, the present disclosure provides solid forms of DOM Form A, e.g., crystalline forms of DOM Form A. In some embodiments, the DOM Form A XRPD profile is substantially similar to that shown in FIG. 72. In some embodiments, the DOM Form A ¹H NMR spectrum is substantially similar to that shown in FIG. 74. In some embodiments, the DOM Form .A TGA profile is substantially similar to that shown in FIG. 75. In some embodiments, the DOM Form A DSC profile is substantially similar to that shown in FIG. 75. In some embodiments, the DOM Form A FT-IR spectrum is substantially similar to that shown in FIG. 76.

In some embodiments, the solid form of DOM Form .A is crystalline DOM Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.0 °2θ, 12.5 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 20; Cu Kα1 radiation). In some embodiments, the solid form of DOM Form A is crystalline DOM Form A characterized by XRPD signals at 12.0 °2θ, 12.5 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM Form A is crystalline DOM Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.8 °2θ, 11.5 °2θ, 12.0 °2θ, 12.5 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 20; Cu Kα1 radiation). In some embodiments, the solid form of DOM Form A is crystalline DOM Form A. characterized by XRPD signals at 5.8 °2θ, 11.5 °2θ, 12.0 °2θ, 12.5 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM Form A. is crystalline DOM Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.5 °2θ, 12.0 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM Form A is crystalline DOM Form A characterized by XRPD signals at 11.5 °2θ, 12.0 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM Form A is crystalline DOM Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.5 °2θ, 12.0 °2θ, 17.2 °2θ, 17.4 °2θ, and 24.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM Form A is DOM Form A characterized by XRPD signals at 11.5 °2θ, 12.0 °2θ, 17.2 °2θ, 17.4 °2θ, and 24.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM Form A is crystalline DOM Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.5 °2θ, 12.0 °2θ, 17.2 °2θ, 17.4 °2θ, 24.9 °2θ, 20.1 °2θ. and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM Form A is DOM Form A characterized by XRPD signals at 11.5 °2θ, 12.0 °2θ, 17.2 °2θ, 17.4 °2θ, 24.9 °2θ, 20.1 °2θ, and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOM Form .A is crystalline DOM Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.5 °2θ, 12.0 °2θ, 17.2 °2θ, 17.4 °2θ, 24.9 °2θ, 20.1 °2θ, 21.1 °2θ, 12.5 °2θ, 24.2 °2θ, and 23.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOM Form A is DOM Form A characterized by XRPD signals at 11.5 °2θ, 12.0 °2θ, 17.2 °2θ, 17.4 °2θ, 24.9 °2θ, 20.1 °2θ, 21.1 °2θ, 12.5 °2θ, 24.2 °2θ, and 23.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOM Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, or thirty XRPD signals selected from those set forth in Table 36.

Table 36. XRPD Signals for DOM Form A

Solid forms of DOI HCI

In some embodiments, the present disclosure provides solid forms of DOI HCI, e.g., crystalline forms of DOI HCI. In some embodiments, the DOI HCI XRPD profile is substantially similar to that, shown in FIG. 79.

In some embodiments, the solid form of DOI HCI is crystalline DOI HCI characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.8 °2θ, 8.2 °2θ, and 10.2 °2θ (.±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOI HCI is crystalline DOI HCI characterized by XRPD signals at 7.8 °2θ, 8.2 °2θ, and 10.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOI HCI is cry stalline DOI HCI characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.8 °2θ, 8.2 °2θ, 10.2 °2θ, 19.4 °2θ, and. 23.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOI HCI is crystalline DOI HCI characterized by XRPD signals at 7.8 °2θ, 8.2 29. 10.2 °2θ, 19.4 20, and 23.5 29 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOI HCI is crystalline DOI HCI characterized by two or more, or three or more XRPD signals selected from the group consisting of 23.5 °2θ, 7.8 °2θ, and 16.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOI HCI is crystalline DOI HCI characterized by XRPD signals at 23.5 °2θ, 7.8 °2θ, and 16.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOI HCI is cry stalline DOI HCI characterized by two or more, or three or more XRPD signals selected from the group consisting of 23.5 °2θ, 7.8 °2θ, 16.5 °2θ, 22.7 °2θ, and 16.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOI HCI is DOI HCI characterized by XRPD signals at of 23.5 °2θ, 7.8 °2θ. 16.5 °2θ, 22.7 °2θ. and 16.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOI HCI is crystalline DOI HCI characterized by two or more, or three or more XRPD signals selected from the group consisting of 23.5 °2θ, 7.8 °2θ, 16.5 °2θ, 22.7 °2θ, 16.3 °2θ, 26.8 °2θ, and 24.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOI HCI is DOI HCI characterized by XRPD signals at 23.5 °2θ, 7.8 °2θ, 16.5 °2θ, 22.7 °2θ, 16.3 °2θ, 26.8 °2θ, and 24.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the solid form of DOI HCI is crystalline DOI HCI characterized by two or more, or three or more XRPD signals selected from the group consisting of 23.5 °2θ, 7.8 °2θ, 16.5 °2θ, 22.7 °2θ, 16.3 °2θ, 26.8 °2θ, 24.2 °2θ, 19.4 °2θ, 16.1 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0,1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). In some embodiments, the solid form of DOI HCI is DOI HCI characterized by XRPD signals at 23.5 °2θ, 7.8 °2θ, 16.5 °2θ, 22.7 °2θ, 16.3 °2θ, 26.8 °2θ, 24.2 °2θ, 19.4 °2θ, 16.1 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

In some embodiments, the crystalline DOI HCI is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, or fifty-five XRPD signals selected from those set forth in Table 37.

Table 37. XRPD Signals for DOI HCI

III. Pharmaceutical Compositions and Formulations In some embodiments, the present disclosure provides a pharmaceutical composition comprising one or more of the solid forms of DOM, DOI, DOB, or DOC, illustrated above, and a pharmaceutically acceptable excipient. Such compositions are suitable for administration to a subject, such as a human subject. The presently disclosed pharmaceutical compositions can be prepared in a wide variety of oral, parenteral and topical dosage forms. Oral preparations include tablets, pills, powder, capsules, lozenges, cachets, slurries, suspensions, etc., suitable for ingestion by the patient. The compositions of the present disclosure can also be administered by injection, that is, intravenously, intramuscularly, intracutaneously, subcutaneously, intraduodenally, or intraperitoneally. Also, the compositions described herein can be administered by inhalation, for example, intranasally. Additionally, the compositions of the present disclosure can be administered transdermally. The compositions of this disclosure can also be administered by intraocular, intravaginal, and intrarectal routes including suppositories, insufflation, powders and aerosol formulations (for examples of steroid inhalants, see Rohatagi, J. Clin. Pharmacol. 35:1187-1193, 1995; Tjwa, Ann. Allergy Asthma Immunol. 75:107-111, 1995). Accordingly, the present disclosure also provides pharmaceutical compositions including a pharmaceutically acceptable carrier or excipient and the solid form of DOM, DOI, DOB, or DOC of the present disclosure. For preparing pharmaceutical compositions from the compounds disclosed herein, pharmaceutically acceptable carriers can be either solid or liquid. Solid form preparations include powders, tablets, pills, capsules, cachets, suppositories, and dispersible granules. A solid carrier can be one or more substances, which may also act as diluents, flavoring agents, binders, preservatives, tablet disintegrating agents, or an encapsulating material. Details on techniques for formulation and administration are well described in the scientific and patent literature, see, e.g., the latest edition of Remington's Pharmaceutical Sciences, Mack Publishing Co, Easton PA ("Remington's"). In powders, the carrier is a finely divided solid, which is in a mixture with the finely divided active component. In tablets, the active component is mixed with the carrier having the necessary binding properties in suitable proportions and compacted in the shape and size desired. The powders and tablets preferably contain from 5% to 70% or 10% to 70% of the compounds of the present disclosure. Suitable solid excipients include, but are not limited to, magnesium carbonate; magnesium stearate; talc; pectin; dextrin; starch; tragacanth; a low melting wax; cocoa butter; carbohydrates; sugars including, but not limited to, lactose, sucrose, mannitol, or sorbitol, starch from com, wheat, rice, potato, or other plants; cellulose such as methyl cellulose, hydroxypropylmethyl-cellulose, or sodium carboxymethylcellulose; and gums including arabic and tragacanth; as well as proteins including, but not limited to, gelatin and collagen. If desired, disintegrating or solubilizing agents may be added, such as the cross-linked polyvinyl pyrrolidone, agar, alginic acid, or a salt thereof, such as sodium alginate. For preparing suppositories, a low melting wax, such as a mixture of fatty acid glycerides or cocoa butter, is first melted and the compounds of the present disclosure are dispersed homogeneously therein, as by stirring. The molten homogeneous mixture is then poured into convenient sized molds, allowed to cool, and thereby to solidify. Liquid form preparations include suspensions, for example, water or water/propylene glycol suspensions. Aqueous suspensions suitable for oral use can be made by dispersing the finely divided active component in water with viscous material, such as natural or synthetic gums, resins, methylcellulose, sodium carboxymethylcellulose, hydroxypropylmethylcellulose, sodium alginate, polyvinylpyrrolidone, gum tragacanth and gum acacia, and dispersing or wetting agents such as a naturally occurring phosphatide (e.g., lecithin), a condensation product of an alkylene oxide with a fatty acid (e.g., polyoxyethylene stearate), a condensation product of ethylene oxide with a long chain aliphatic alcohol (e.g., heptadecaethylene oxycetanol), a condensation product of ethylene oxide with a partial ester derived from a fatty acid and a hexitol (e.g., polyoxyethylene sorbitol mono-oleate), or a condensation product of ethylene oxide with a partial ester derived from fatty acid and a hexitol anhydride (e.g., polyoxyethylene sorbitan mono-oleate). The aqueous suspension can also contain one or more preservatives such as ethyl or n-propyl p-hydroxybenzoate, one or more coloring agents, one or more flavoring agents and one or more sweetening agents, such as sucrose, aspartame or saccharin. Formulations can be adjusted for osmolarity. Also included are solid form preparations, which are intended to be converted, shortly before use, to liquid form preparations for oral administration. Such liquid forms include suspensions. These preparations may contain, in addition to the active component, colorants, flavors, stabilizers, buffers, artificial and natural sweeteners, dispersants, thickeners, solubilizing agents, and the like. Oil suspensions can be formulated by suspending the compound of the present disclosure in a vegetable oil, such as arachis oil, olive oil, sesame oil or coconut oil, or in a mineral oil such as liquid paraffin; or a mixture of these. The oil suspensions can contain a thickening agent, such as beeswax, hard paraffin or cetyl alcohol. Sweetening agents can be added to provide a palatable oral preparation, such as glycerol, sorbitol or sucrose. These formulations can be preserved by the addition of an antioxidant such as ascorbic acid. As an example of an injectable oil vehicle, see Minto, J. Pharmacol. Exp. Ther.281:93-102, 1997. The pharmaceutical formulations of the disclosure can also be in the form of oil-in-water emulsions. The oily phase can be a vegetable oil or a mineral oil, described above, or a mixture of these. Suitable emulsifying agents include naturally-occurring gums, such as gum acacia and gum tragacanth, naturally occurring phosphatides, such as soybean lecithin, esters or partial esters derived from fatty acids and hexitol anhydrides, such as sorbitan mono-oleate, and condensation products of these partial esters with ethylene oxide, such as polyoxyethylene sorbitan mono-oleate. The emulsion can also contain sweetening agents and flavoring agents, as in the formulation of syrups and elixirs. Such formulations can also contain a demulcent, a preservative, or a coloring agent. The compositions of the present disclosure can also be delivered as microspheres for slow release in the body. For example, microspheres can be formulated for administration via intradermal injection of drug- containing microspheres, which slowly release subcutaneously (see Rao, J. Biomater Sci. Polym. Ed.7:623-645, 1995; as biodegradable and injectable gel formulations (see, e.g., Gao Pharm. Res.12:857-863, 1995); or, as microspheres for oral administration (see, e.g., Eyles, J. Pharm. Pharmacol.49:669-674, 1997). Both transdermal and intradermal routes afford constant delivery for weeks or months. In some embodiments, the pharmaceutical compositions of the present disclosure can be formulated for parenteral administration, such as intravenous (IV) administration or administration into a body cavity or lumen of an organ. The formulations for administration will commonly comprise a solution or suspension of the compositions of the present disclosure dissolved or suspended in a pharmaceutically acceptable carrier. Among the acceptable vehicles and solvents that can be employed are water and Ringer's solution, an isotonic sodium chloride. In addition, sterile fixed oils can conventionally be employed as a solvent or suspending medium. For this purpose, any bland fixed oil can be employed including synthetic mono- or diglycerides. In addition, fatty acids such as oleic acid can likewise be used in the preparation of injectables. These solutions or suspensions are sterile and generally free of undesirable matter. These formulations may be sterilized by conventional, well known sterilization techniques. The formulations may contain pharmaceutically acceptable auxiliary substances as required to approximate physiological conditions such as pH adjusting and buffering agents, toxicity adjusting agents, e.g., sodium acetate, sodium chloride, potassium chloride, calcium chloride, sodium lactate and the like. The concentration of the compositions of the present disclosure in these formulations can vary widely, and will be selected primarily based on fluid volumes, viscosities, body weight, and the like, in accordance with the particular mode of administration selected and the patient's needs. For IV administration, the formulation can be a sterile injectable preparation, such as a sterile injectable aqueous or oleaginous suspension. This suspension can be formulated according to the known art using those suitable dispersing or wetting agents and suspending agents. The sterile injectable preparation can also be a sterile injectable solution or suspension in a nontoxic parenterally-acceptable diluent or solvent, such as a solution of 1,3- butanediol. In some embodiments, the formulations of the compositions of the present disclosure can be delivered by the use of liposomes which fuse with the cellular membrane or are endocytosed, for example, by employing ligands attached to the liposome, or attached directly to the oligonucleotide, that bind to surface membrane protein receptors of the cell resulting in endocytosis. By using liposomes, particularly where the liposome surface carries ligands specific for target cells, or are otherwise preferentially directed to a specific organ, one can focus the delivery of the compositions of the present disclosure into the target cells in vivo. (See, e.g., Al-Muhammed, J. Microencapsul.13:293-306, 1996; Chonn, Curr. Opin. Biotechnol.6:698-708, 1995; Ostro, Am. J. Hosp. Pharm.46:1576-1587, 1989). IV. Administration The compositions of the present disclosure can be administered by any suitable means, including oral, parenteral and topical methods. Transdermal administration methods, by a topical route, can be formulated as applicator sticks, suspensions, creams, ointments, pastes, jellies, paints, powders, and aerosols. The pharmaceutical preparation is preferably in unit dosage form. In such form the preparation is subdivided into unit doses containing appropriate quantities of the compounds of the present disclosure. The unit dosage form can be a packaged preparation, the package containing discrete quantities of preparation, such as packeted tablets, capsules, and powders in vials or ampoules. Also, the unit dosage form can be a capsule, tablet, cachet, or lozenge itself, or it can be the appropriate number of any of these in packaged form. The compound of the present disclosure can be present in any suitable amount, and can depend on various factors including, but not limited to, weight and age of the subject, state of the disease, and the like as is known to those of ordinary skill in the art. The DOM, DOI, DOB, or DOC forms administered herein typically are administered to provide from between about 0.5 mg and about 35 mg, or about 1mg, or about 2mg, or about 3mg, or about 4mg, or about 5 mg, or about 6mg, or about 7mg, or about 8mg, or about 9mg, or about 10mg, or about 11mg, or about 12mg, or about 13mg, or about 14mg, or about 15mg 20mg, or about 25mg, or about 30mg, or about 35 mg. Suitable dosage ranges for the compounds disclosed herein include from about 0.1 mg to about 10,000 mg, or about 1 mg to about 1000 mg, or about 10 mg to about 750 mg, or about 25 mg to about 500 mg, or about 50 mg to about 250 mg. Suitable dosages for the compound of the present invention include about 1 mg, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400, 500, 600, 700, 800, 900 or 1000 mg. The compounds disclosed herein can be administered at any suitable frequency, interval and duration. For example, the compounds can be administered once an hour, or two, three or more times an hour, once a day, or two, three, or more times per day, or once every 2, 3, 4, 5, 6, or 7 days, so as to provide the preferred dosage level. When the compound of the present invention is administered more than once a day, representative intervals include 5, 10, 15, 20, 30, 45 and 60 minutes, as well as 1, 2, 4, 6, 8, 10, 12, 16, 20, and 24 hours. The compound of the present invention can be administered once, twice, or three or more times, for an hour, for 1 to 6 hours, for 1 to 12 hours, for 1 to 24 hours, for 6 to 12 hours, for 12 to 24 hours, for a single day, for 1 to 7 days, for a single week, for 1 to 4 weeks, for a month, for 1 to 12 months, for a year or more, or even indefinitely. The composition can also contain other compatible therapeutic agents. The compounds described herein can be used in combination with one another, with other active agents known to be useful in modulating a glucocorticoid receptor, or with adjunctive agents that may not be effective alone, but may contribute to the efficacy of the active agent. The compounds of the present disclosure can be co-administered with a second active agent. Co-administration includes administering the compound of the present disclosure and active agent within 0.5, 1, 2, 4, 6, 8, 10, 12, 16, 20, or 24 hours of each other. Co-administration also includes administering the compound of the present disclosure and active agent simultaneously, approximately simultaneously (e.g., within about 1, 5, 10, 15, 20, or 30 minutes of each other), or sequentially in any order. Moreover, the compound of the present disclosure and the active agent can each be administered once a day, or two, three, or more times per day so as to provide the preferred dosage level per day. In some embodiments, co-administration can be accomplished by co-formulation, such as by preparing a single pharmaceutical composition including both the compound of the present disclosure and a second active agent. In other embodiments, the compound of the present disclosure and the second active agent can be formulated separately. The disclosed compounds and the second active agent can be present in the compositions of the present disclosure in any suitable weight ratio, such as from about 1:100 to about 100: 1 (w/w), or about 1 :50 to about 50: 1, or about 1 :25 to about 25: 1, or about 1:10 to about 10:1, or about 1:5 to about 5:1 (w/w). The compound of the present disclosure and the second active agent can be present in any suitable weight ratio, such as about 1: 100 (w/w), 1:50, 1:25, 1:10, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 10:1, 25:1, 50:1 or 100:1 (w/w). Other dosages and dosage ratios of the compound of the present disclosure and the active agent are suitable in the compositions and methods disclosed herein. V. Methods of Treatment The solid forms of DOM, DOI, DOB, or DOC of the present disclosure can be used for increasing neuronal plasticity. The compounds of the present disclosure can also be used to treat any brain disease. The compounds of the present disclosure can also be used for increasing at least one of translation, transcription or secretion of neurotrophic factors. In some embodiments, the methods described herein are for treating a disease or disorder that is a brain disease or disorder. In some embodiments, the methods described herein are for increasing at least one of translation, transcription or secretion of neurotrophic factors. In some embodiments, the compositions provided herein have, for example, anti- addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof. In some embodiments, the brain disorder is a neuropsychiatric disease. In some embodiments, the methods described herein are for treating a disease or disorder that is a neuropsychiatric disease. In some embodiments, the neuropsychiatric disease is a mood or anxiety disorder. In some embodiments, brain disorders include, for example, migraine, cluster headache, post-traumatic stress disorder (PTSD), anxiety, depression, panic disorder, suicidality, schizophrenia, and addiction (e.g., substance abuse disorder). In some embodiments, brain disorders include, for example, migraines, addiction (e.g., substance use disorder for example alcohol abuse, opiate addition, or abuse), depression, and anxiety. In some embodiments, the brain disease or disorder is a neurodegenerative disorder, Alzheimer’s disease or Parkinson’s disease. In some embodiments, the brain disease or disorder is psychological disorder, depression, addiction, anxiety, or a post-traumatic stress disorder. In some embodiments, the brain disorder is depression. In some embodiments, the brain disorder is addiction. In some embodiments, the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury or substance use disorder. In some embodiments, the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, or substance use disorder. In some embodiments, the brain disorder is stroke or traumatic brain injury. In some embodiments, the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, or substance use disorder. In some embodiments, the brain disorder is schizophrenia. In some embodiments, the brain disorder is alcohol use disorder. In some embodiments, a compound of the present disclosure is used to treat neurological diseases. In some embodiments, the methods described herein are for treating a disease or disorder that is a neurological disease. For example, a compound provided herein can exhibit, anti-addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof. In some embodiments, the neurological disease is a neuropsychiatric disease. In some embodiments, the neuropsychiatric disease is a mood or anxiety disorder. In some embodiments, the neurological disease is a migraine, headaches (e.g., cluster headache), post-traumatic stress disorder (PTSD), anxiety, depression, neurodegenerative disorder, Alzheimer’s disease, Parkinson’s disease, psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, hypoxic brain injury, Chronic traumatic encephalopathy (CTE), traumatic brain injury, dementia, and addiction (e.g., substance use disorder). In some embodiments, the neurological disease is a migraine or cluster headache. In some embodiments, the neurological disease is a neurodegenerative disorder, dementia, Alzheimer’s disease, or Parkinson’s disease. In some embodiments, the neurological disease is dementia. In some embodiments, the neurological disease is a psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, post-traumatic stress disorder (PTSD), addiction (e.g., substance use disorder), depression, or anxiety. In some embodiments, the neuropsychiatric disease is a psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, post-traumatic stress disorder (PTSD), addiction (e.g., substance use disorder), depression, or anxiety. In some embodiments, the neuropsychiatric disease or neurological disease is post- traumatic stress disorder (PTSD), addiction (e.g., substance use disorder), schizophrenia, depression, or anxiety. In some embodiments, the neuropsychiatric disease or neurological disease is addiction (e.g., substance use disorder). In some embodiments, the neuropsychiatric disease or neurological disease is depression. In some embodiments, the neuropsychiatric disease or neurological disease is anxiety. In some embodiments, the neuropsychiatric disease or neurological disease is post-traumatic stress disorder (PTSD). In some embodiments, the neurological disease is stroke or traumatic brain injury. In some embodiments, the neuropsychiatric disease or neurological disease is schizophrenia. In some embodiments, the methods described herein are for increasing neuronal plasticity and has, for example, anti-addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof. In some embodiments, decreased neuronal plasticity is associated with a neuropsychiatric disease. In some embodiments, a compound of the present disclosure is used for increasing neuronal plasticity. In some embodiments, the compounds described herein are used for treating a brain disorder. In some embodiments, the compounds described herein are used for increasing at least one of translation, transcription, or secretion of neurotrophic factors. In some embodiments, the present disclosure provides a method of treating a disease, including administering to a subject in need thereof, a therapeutically effective amount of a compound of the present disclosure. In some embodiments, the disease is a musculoskeletal pain disorder including fibromyalgia, muscle pain, joint stiffness, osteoarthritis, rheumatoid arthritis, and muscle cramps. In some embodiments, the present disclosure provides a method of treating a disease of women’s reproductive health including premenstrual dysphoric disorder (PMDD), premenstrual syndrome (PMS), post-partum depression, and menopause. Diseases of particular interest include depression and related conditions. Accordingly, in some embodiments, the disease or disorder treated herein is depression or a disease or disorder related to depression. In some embodiments, the depression is major depressive disorder, persistent depressive disorder, bipolar disorder, treatment resistant depression (TRD), postpartum depression, premenstrual dysphoric disorder, or seasonal affective disorder. In some embodiments, the disease or disorder related to depression is anxiety. In some embodiments, methods of treating depression or a disease or disorder related to depression comprise treating the symptoms associated with the depression or the disease or disorder related to depression. Described herein are methods of treating depression or a disease or disorder related to depression in a subject in need thereof, the method comprising administering to the subject a psychedelic and a serotonin receptor modulator, wherein the serotonin receptor modulator is administered at most about 3 hours prior to the release of the psychedelic. In some embodiments, the depression is major depressive disorder, persistent depressive disorder, bipolar disorder, treatment resistant depression (TRD), postpartum depression, premenstrual dysphoric disorder, or seasonal affective disorder. In some embodiments, the disease or disorder related to depression is anxiety. In some embodiments, methods of treating depression or a disease or disorder related to depression comprise treating the symptoms associated with the depression or the disease or disorder related to depression. In some embodiments, the DOM, DOI, DOB, or DOC solid forms of the present disclosure have activity as 5-HT_2A modulators. In some embodiments, the compounds of the present disclosure elicit a biological response by activating the 5-HT_2A receptor (e.g., allosteric modulation or modulation of a biological target that activates the 5-HT_2A receptor). 5-HT_2A agonism has been correlated with the promotion of neural plasticity (Ly et al., 2018). 5-HT_2A antagonists abrogate the neuritogenesis and spinogenesis effects of hallucinogenic compounds with 5-HT_2A agonist activity, for example., DMT or LSD. In some embodiments, the compounds of the present disclosure are 5-HT_2A modulators and promote neural plasticity (e.g., cortical structural plasticity). In some embodiments, the compounds of the present disclosure are selective 5-HT_2A modulators and promote neural plasticity (e.g., cortical structural plasticity). In some embodiments, promotion of neural plasticity includes, for example, increased dendritic spine growth, increased synthesis of synaptic proteins, strengthened synaptic responses, increased dendritic arbor complexity, increased dendritic branch content, increased spinogenesis, increased neuritogenesis, or any combination thereof. In some embodiments, increased neural plasticity includes, for example, increased cortical structural plasticity in the anterior parts of the brain. In some embodiments, the 5-HT_2A modulators (e.g., 5-HT_2A agonists) are non- hallucinogenic. In some embodiments, non-hallucinogenic 5-HT_2A modulators (e.g., 5-HT_2A agonists) are used to treat neurological diseases, which modulators do not elicit dissociative side- effects. In some embodiments, the hallucinogenic potential of the compounds described herein is assessed in vitro. In some embodiments, the hallucinogenic potential assessed in vitro of the compounds described herein is compared to the hallucinogenic potential assessed in vitro of hallucinogenic homologs. In some embodiments, the compounds described herein elicit less hallucinogenic potential in vitro than the hallucinogenic homologs. In some embodiments, serotonin receptor modulators, such as modulators of serotonin receptor 2A (5-HT_2A modulators, e.g., 5-HT_2A agonists), are used to treat a brain disorder. The presently disclosed compounds can function as 5-HT_2A agonists alone, or in combination with a second therapeutic agent that also is a 5-HT_2A modulator. In such cases the second therapeutic agent can be an agonist or an antagonist. In some instances, it may be helpful administer a 5- HT_2A antagonist in combination with a. compound of the present disclosure to mitigate undesirable effects of 5-HT_2A agonism, such as potential hallucinogenic effects. Serotonin receptor modulators useful as second therapeutic agents for combination therapy as described herein are known to those of skill in the art and include, without limitation, ketanserin, volinanserin (MDL-100907), eplivanserin (SR-46349), pimavanserin (ACP-103), glemanserin (MDL-11939), ritanserin, flibanserin, nelotanserin, blonanserin, mianserin, mirtazapine, roluperiodone (CYR-101, MIN-101), quetiapine, olanzapine, altansenn, acepromazine, nefazodone, risperidone, pruvansenn, AC-90179, AC-279, adatansenn, fananserin, HY10275, benanserin, butanserin, manserin, iferanserin, lidanserin, pelanserin, segansenn, tropanserin, lorcaserin, ICI-169369, methysergide, trazodone, cinitapride, cyproheptadine, brexpiprazole, cariprazine, agomelatine, setoperone, 1-(1-Naphthyl)piperazine, LY-367265, pirenperone, metergoline, deramciclane, amperozide, cinanserin, LY-86057, GSK-215083, cyamemazine, mesulergine, BF-1, LY-215840, sergolexole, spiramide, LY-53857, amesergide, LY-108742, pipamperone, LY-314228, 5-I-R91150, 5-MeO-NBpBrT, 9-Aminomethyl-9,10- dihydroanthracene, maprazme, SB-215505, SB-204741 , SB-206553, SB-242084, LY-272015, SB-243213, SB-200646, RS-102221, zotepine, clozapine, chlorpromazine, sertindole, iloperidone, paliperidone, asenapine, amisulpride, aripiprazole, lurasidone, ziprasidone, lumateperone, perospirone, mosapramine, AMD A (9-Aminomethyl-9,10-dihydroanthracene), methiothepin, buspirone, an extended-release form of olanzapine (e.g., ZYPREXA RELPREW), an extended-release form of quetiapine, an extended-release form of risperidone (e.g., Risperdal Consta), an extended-release form of paliperidone (e.g., Invega Sustenna and Invega Trinza), an extended-release form of fluphenazine decanoate including Prolixin Decanoate, an extended-release form of aripiprazole lauroxil including Aristada, an extended- release form of aripiprazole including Abilify Maintena, 3-(2-(4-(4-Fluorobenzoyl)piperazin-l- yl)ethyl)-5-methyl-5-phenyhmidazolidme-2,4-dione, 3-(2-(4-Benzhydrylpiperazin-l-yl)ethyl)-5-methyl-5-phe- nylimidazolidine-2, 4-dione, 3-(3-(4-(2-Fluorophenyl)piperazin-l-yl)propyI)-5-me- thyl-5-phenylimidazolidme-2,4-dione, 3-(3-(4-(3-Fluorophenyl)piperazin-l-yl)propyl)-5-me- thyl-5-phenylimidazolidine-2, 4-dione, 3-(3-(4-(4-Fluorophenyl)piperazin-l-yl)propyl)-5-me- thy l-5-phenylimidazohdine-2, 4-dione, 3-(3-(4-(4-Fluorobenzoyl)piperazin-1 -yl)propyl)-5- methy l-5-phenylimidazolidine-2, 4-dione, 3 -(2-(4-(4-Fluorobenzoy l)piperazin- 1 -yl)ethyl)-8- phenyl-l,3-diazaspiro[4.5]decane-2, 4-dione, 3-(2-(4-Benzhydrylpiperazin-1 -yl)ethyl)-8-phenyl- l,3-diazaspiro[4.5]decane-2, 4-dione, 3-(3-(4-(2-Fluorophenyl)piperazin-l-yl)propyl)-8-phe- nyl-1 ,3-diazaspiro[4.5]decane-2, 4-dione, 3-(3-(4-(3-Fluorophenyl)piperazin-l -yl)propyl)-8-phe- nyl-l,3-diazaspiro[4.5]decane-2, 4-dione, 3-(3-(4-(4-Fluorophenyl)piperazin-l-yl)propyl)-8-phe- nyl-l,3-diazaspiro[4.5]decane-2, 4-dione, and 3-(3-(4-(4-Fluorobenzoyl)piperazin-l-yl)propyl)-8- phenyl-l,3-diazaspiro[4.5]decane-2, 4-dione, or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analogue, derivative, prodrug, or combinations thereof. In some embodiments, the serotonin receptor modulator is ketanserin or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analogue, derivative, or prodrug thereof. In some embodiments, the serotonin receptor modulator is pimavanserin or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analogue, derivative, or prodrug thereof. In some embodiments, the serotonin receptor modulator is eplivanserin or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analogue, derivative, or prodrug thereof. In some embodiments, the serotonin receptor modulator is flibanserin or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analogue, derivative, or prodrug thereof. In some embodiments, the serotonin receptor modulator is roluperiodone or a. pharmaceutically acceptable salt, solvate, metabolite, deuterated analogue, derivative, or prodrug thereof. In some embodiments, the serotonin receptor modulator is administered prior to a compound disclosed herein, such as about one or about three hours prior to administration of a compound disclosed herein. In some embodiments, the serotonin receptor modulator is administered at most about one hour prior to the presently disclosed compound. Thus, in some embodiments of combination therapy with the presently disclosed compounds, the second therapeutic agent is a serotonin receptor modulator.

In some embodiments the second therapeutic agent serotonin receptor modulator is provided at a. dose of from about 10 mg to about 350 mg. In some embodiments, the serotonin receptor modulator is provided at a. dose of from about 20 mg to about 200 mg. In some embodiments, the serotonin receptor modulator is provided at a dose of from about 10 mg to about 100 mg. In certain such embodiments, the compound of the present disclosure is provided at a dose of from about 10 mg to about 100 mg, or from about 20 to about 200 mg, or from about 15 to about 300 mg, and the serotonin receptor modulator is provided at a dose of about 10 mg to about 100 mg. In some embodiments, non-hallucinogenic 5-HT2_A modulators (e.g., 5-HT2_A agonists) are used to treat neurological diseases. In some embodiments, the neurological diseases comprise decreased neural plasticity, decreased cortical structural plasticity, decreased 5-HT_2A receptor content, decreased dendritic arbor complexity, loss of dendritic spines, decreased dendritic branch content, decreased spinogenesis, decreased neuritogenesis, retraction of neurites, or any combination thereof. In some embodiments, non-hallucinogenic 5-HT_2A modulators (e.g., 5-HT_2A agonists) are used for increasing neuronal plasticity. In some embodiments, non-hallucinogenic 5-HT_2A modulators (e.g., 5-HT_2A agonists) are used for treating a brain disorder. In some embodiments, non-hallucinogenic 5-HT_2A modulators (e.g., 5-HT_2A agonists) are used for increasing at least one of translation, transcription, or secretion of neurotrophic factors. In some embodiments the presently disclosed compounds are given to patients in a low dose that is lower than would produce noticeable psychedelic effects but high enough to provide a therapeutic benefit. This dose range is predicted to be between 200ug (micrograms) and 2mg. A) Methods for Increasing Neuronal Plasticity Neuronal plasticity refers to the ability of the brain to change structure and/or function throughout a subject’s life. New neurons can be produced and integrated into the central nervous system throughout the subject’s life. Increasing neuronal plasticity includes, but is not limited to, promoting neuronal growth, promoting neuritogenesis, promoting synaptogenesis, promoting dendritogenesis, increasing dendritic arbor complexity, increasing dendritic spine density, and increasing excitatory synapsis in the brain. In some embodiments, increasing neuronal plasticity comprises promoting neuronal growth, promoting neuritogenesis, promoting synaptogenesis, promoting dendritogenesis, increasing dendritic arbor complexity, and increasing dendritic spine density. In some embodiments, increasing neuronal plasticity by treating a subject with one or more of the disclosed compound can treat neurodegenerative disorder, Alzheimer’s, Parkinson’s disease, psychological disorder, depression, addiction, anxiety, post-traumatic stress disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, or substance use disorder. In some embodiments, the present disclosure provides methods for increasing neuronal plasticity, comprising contacting a neuronal cell with a compound of the present disclosure. In some embodiments, increasing neuronal plasticity improves a brain disorder described herein. In some embodiments, a compound of the present disclosure is used to increase neuronal plasticity. In some embodiments, the compounds used to increase neuronal plasticity have, for example, anti- addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof. In some embodiments, decreased neuronal plasticity is associated with a neuropsychiatric disease. In some embodiments, the neuropsychiatric disease is a mood or anxiety disorder. In some embodiments, the neuropsychiatric disease includes, for example, migraine, cluster headache, post-traumatic stress disorder (PTSD), schizophrenia, anxiety, depression, and addiction (e.g., substance abuse disorder). In some embodiments, brain disorders include, for example, migraines, addiction (e.g., substance use disorder), depression, and anxiety. In some embodiments, the experiment or assay to determine increased neuronal plasticity of any compound of the present disclosure is a phenotypic assay, a dendritogenesis assay, a spinogenesis assay, a synaptogenesis assay, a Sholl analysis, a concentration-response experiment, a 5-HT_2A agonist assay, a 5-HT_2A antagonist assay, a 5-HT_2A binding assay, or a 5- HT_2A blocking experiment (e.g., ketanserin blocking experiments). In some embodiments, the experiment or assay to determine the hallucinogenic potential of any compound of the present disclosure is a mouse head-twitch response (HTR) assay. In some embodiments, the present disclosure provides a method for increasing neuronal plasticity, comprising contacting a neuronal cell with a compound disclosed herein. B) Methods of Treating a Brain Disorder In some embodiments, the present disclosure provides a method of treating a disease, including administering to a subject in need thereof, a therapeutically effective amount of DOM, DOI, DOB, or DOC of the present disclosure. In some embodiments, the disease is a musculoskeletal pain disorder including fibromyalgia, muscle pain, joint stiffness, osteoarthritis, rheumatoid arthritis, and muscle cramps. In some embodiments, the present disclosure provides a method of treating a disease of women’s reproductive health including premenstrual dysphoric disorder (PMDD), premenstrual syndrome (PMS), post-partum depression, and menopause. In some embodiments, the present disclosure provides a method of treating a brain disorder, including administering to a subject in need thereof, a therapeutically effective amount of a compound of the present disclosure. In some embodiments, the present disclosure provides a method of treating a brain disorder with combination therapy, including administering to a subject in need thereof, a therapeutically effective amount of a compound of the present disclosure and at least one additional therapeutic agent. In some embodiments, 5-HT_2A modulators (e.g., 5-HT_2A agonists) are used to treat a brain disorder. In some embodiments, the brain disorders comprise decreased neural plasticity, decreased cortical structural plasticity, decreased 5-HT_2A receptor content, decreased dendritic arbor complexity, loss of dendritic spines, decreased dendritic branch content, decreased spinogenesis, decreased neuritogenesis, retraction of neurites, or any combination thereof. In some embodiments, a compound of the present disclosure is used to treat brain disorders. In some embodiments, the compounds have, for example, anti- addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof. In some embodiments, the brain disorder is a neuropsychiatric disease. In some embodiments, the neuropsychiatric disease is a mood or anxiety disorder. In some embodiments, brain disorders include, for example, migraine, cluster headache, post-traumatic stress disorder (PTSD), anxiety, depression, panic disorder, suicidality, schizophrenia, and addiction (e.g., substance abuse disorder). In some embodiments, brain disorders include, for example, migraines, addiction (e.g., substance use disorder), depression, and anxiety. In some embodiments, the present disclosure provides a method of treating a brain disorder, comprising administering to a subject in need thereof a therapeutically effective amount of a compound disclosed herein. In some embodiments, the brain disorder is a neurodegenerative disorder, Alzheimer’s, Parkinson’s disease, psychological disorder, depression, addiction, anxiety, post-traumatic stress disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, or substance use disorder. In some embodiments, the brain disorder is a neurodegenerative disorder, Alzheimer’s, or Parkinson’s disease. In some embodiments, the brain disorder is a psychological disorder, depression, addiction, anxiety, or a post-traumatic stress disorder. In some embodiments, the brain disorder is depression. In some embodiments, the brain disorder is addiction. In some embodiments, the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury or substance use disorder. In some embodiments, the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, or substance use disorder. In some embodiments, the brain disorder is stroke or traumatic brain injury. In some embodiments, the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, or substance use disorder. In some embodiments, the brain disorder is schizophrenia. In some embodiments, the brain disorder is alcohol use disorder. In some embodiments, the method further comprises administering one or more additional therapeutic agent that is lithium, olanzapine (Zyprexa), quetiapine (Seroquel), risperidone (Risperdal), ariprazole (Abilify), ziprasidone (Geodon), clozapine (Clozaril), divalproex sodium (Depakote), lamotrigine (Lamictal), valproic acid (Depakene), carbamazepine (Equetro), topiramate (Topamax), levomilnacipran (Fetzima), duloxetine (Cymbalta, Yentreve), venlafaxine (Effexor), citalopram (Celexa), fluvoxamine (Luvox), escitalopram (Lexapro), fluoxetine (Prozac), paroxetine (Paxil), sertraline (Zoloft), clomipramine (Anafranil), amitriptyline (Elavil), desipramine (Norpramin), imipramine (Tofranil), nortriptyline (Pamelor), phenelzine (Nardil), tranylcypromine (Parnate), diazepam (Valium), alprazolam (Xanax), or clonazHSDP^^.ORQRSLQ^^ In certain embodiments of the method for treating a brain disorder with a solid form disclosed herein, a second therapeutic agent that is an empathogenic agent is administered. Examples of suitable empathogenic agents for use in combination with the present solid forms include phenethylamines, such as 3,4-methylene- dioxymethamphetamine (MDMA), and analogs thereof. Other suitable empathogenic agents for use in combination with the presently disclosed compounds include, without limitation, N-Allyl-3,4-methylenedioxy-amphetamine (MDAL) N-Butyl-3,4-methylenedioxyamphetamine (MDBU) N-Benzyl-3,4-methylenedioxyamphetamine (MDBZ) N-Cyclopropylmethyl-3,4-methylenedioxyamphetamine (MDCPM) N,N-Dimethyl-3,4-methylenedioxyamphetamine (MDDM) N-Ethyl-3,4-methylenedioxyamphetamine (MDE; MDEA) N-(2-Hydroxyethyl)-3,4-methylenedioxy amphetamine (MDHOET) N-Isopropyl-3,4-methylenedioxyamphetamine (MDIP) N-Methyl-3,4-ethylenedioxyamphetamine (MDMC) N-Methoxy-3,4-methylenedioxyamphetamine (MDMEO) N-(2-Methoxyethyl)-3,4-methylenedioxyamphetamine (MDMEOET) alpha,alpha,N-Trimethyl-3,4-methylenedioxyphenethylamine (MDMP; 3,4-methylenedioxy-N- methylphentermine) N-Hydroxy-3,4-methylenedioxyamphetamine (MDOH) 3,4-Methylenedioxyphenethylamine (MDPEA) alpha,alpha-Dimethyl-3,4-methylenedioxyphenethylamine (MDPH; 3,4- methylenedioxyphentermine) N-Propargyl-3,4-methylenedioxyamphetamine (MDPL) Methylenedioxy-2-aminoindane (MDAI) 1,3-Benzodioxolyl-N-methylbutanamine (MBDB) N-methyl-1,3-benzodioxolylbutanamine (MBDB) 3,4-methylenedioxy-N-methyl-Į-ethylphenylethylamine 3,4-Methylenedioxyamphetamine (MDA) Methylone (also known as 3,4-methylenedioxy-N-methylcathinone) Ethylone (also known as 3,4-methylenedioxy-N-ethylcathinone) GHB (also known as Gamma Hydroxybutyrate or sodium oxybate) N-Propyl-3,4-methylenedioxyamphetamine (MDPR), and the like. In some embodiments, the compounds of the present disclosure are used in combination with the standard of care therapy for a neurological disease described herein. Non- limiting examples of the standard of care therapies, may include, for example, lithium, olanzapine, quetiapine, risperidone, ariprazole, ziprasidone, clozapine, divalproex sodium, lamotrigine, valproic acid, carbamazepine, topiramate, levomilnacipran, duloxetine, venlafaxine, citalopram, fluvoxamine, escitalopram, fluoxetine, paroxetine, sertraline, clomipramine, amitriptyline, desipramine, imipramine, nortriptyline, phenelzine, tranylcypromine, diazepam, alprazolam, clonazepam, or any combination thereof. Nonlimiting examples of standard of care therapy for depression are sertraline, fluoxetine, escitalopram, venlafaxine, or aripiprazole. Non-limiting examples of standard of care therapy for depression are citralopram, escitalopram, fluoxetine, paroxetine, diazepam, or sertraline. Additional examples of standard of care therapeutics are known to those of ordinary skill in the art. C) Methods of increasing at least one of translation, transcription, or secretion of neurotrophic factors Neurotrophic factors refers to a family of soluble peptides or proteins which support the survival, growth, and differentiation of developing and mature neurons. Increasing at least one of translation, transcription, or secretion of neurotrophic factors can be useful for, but not limited to, increasing neuronal plasticity, promoting neuronal growth, promoting neuritogenesis, promoting synaptogenesis, promoting dendritogenesis, increasing dendritic arbor complexity, increasing dendritic spine density, and increasing excitatory synapsis in the brain. In some embodiments, increasing at least one of translation, transcription, or secretion of neurotrophic factors can increasing neuronal plasticity. In some embodiments, increasing at least one of translation, transcription, or secretion of neurotrophic factors can promoting neuronal growth, promoting neuritogenesis, promoting synaptogenesis, promoting dendritogenesis, increasing dendritic arbor complexity, and/or increasing dendritic spine density. In some embodiments, 5-HT_2A modulators (e.g., 5-HT_2A agonists) are used to increase at least one of translation, transcription, or secretion of neurotrophic factors. In some embodiments, a compound of the present disclosure is used to increase at least one of translation, transcription, or secretion of neurotrophic factors. In some embodiments, increasing at least one of translation, transcription or secretion of neurotrophic factors treats a migraine, headaches (e.g., cluster headache), post-traumatic stress disorder (PTSD), anxiety, depression, neurodegenerative disorder, Alzheimer’s disease, Parkinson’s disease, psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, and addiction (e.g., substance use disorder). In some embodiments, the experiment or assay used to determine increase translation of neurotrophic factors includes ELISA, western blot, immunofluorescence assays, proteomic experiments, and mass spectrometry. In some embodiments, the experiment or assay used to determine increase transcription of neurotrophic factors includes gene expression assays, PCR, and microarrays. In some embodiments, the experiment or assay used to determine increase secretion of neurotrophic factors includes ELISA, western blot, immunofluorescence assays, proteomic experiments, and mass spectrometry. In some embodiments, the present disclosure provides a method for increasing at least one of translation, transcription or secretion of neurotrophic factors, comprising contacting a neuronal cell with a compound disclosed herein. VI. Combination therapy In particular embodiments of treating the disorders described above, combination therapy is used as described herein. In such therapy a form of DOM, DOI, DOB, or DOC described herein is administered in combination with a serotonin receptor modulator. In certain embodiments the serotonin receptor modulator is selected from the group consisting of altanserin, blonanserin, eplivanserin, glemanserin, volinanserin, ketanserin, ritanserin, pimavanserin, nelotanserin, pruvanserin, and flibanserin. In one embodiment, the serotonin receptor modulator is selected from the group consisting of serotonin receptor modulator is selected from the group consisting of eplivanserin, volinanserin, ketanserin, ritanserin, pimavanserin, nelotanserin, pruvanserin, flibanserin, olanzapine, quetiapine, risperidone, and buspirone. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM, DOI, DOB, or DOC is eplivanserin and, wherein the eplivanserin is administered in about 1 mg to about 40 mg, or about 5 mg to about 10 mg, and the DOM, DOI, DOB, or DOC is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered in about 1 mg to about 60 mg, or about 5 mg to about 20 mg, and the DOM, DOI, DOB, or DOC is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM, DOI, DOB, or DOC is ketanserin, wherein the ketanserin is administered in about 10 mg to about 80 mg, about 30 mg to about 50 mg, or about 40 mg and the DOM, DOI, DOB, or DOC is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM, DOI, DOB, or DOC is ritanserin, wherein the ritanserin is administered in about 1 mg to about 40 mg, or about 2.5 mg to about 10 mg, and the DOM, DOI, DOB, or DOC is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered in about 1 mg to about 60 mg, or about 17 mg to about 34 mg, and the DOM, DOI, DOB, or DOC is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM, DOI, DOB, or DOC is nelotanserin, wherein the nelotanserin is administered in about 1 mg to about 80 mg, or about 40 mg to about 80 mg, and the DOM, DOI, DOB, or DOC is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM, DOI, DOB, or DOC is pruvanserin, wherein the pruvanserin is administered in about 1 mg to about 40 mg, or about 3 mg to about 10 mg, and the DOM, DOI, DOB, or DOC is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM, DOI, DOB, or DOC is flibanserin, wherein the flibanserin is administered in about 10 mg to about 200 mg, or about 80 mg to about 120 mg, or about 100 mg and the DOM, DOI, DOB, or DOC is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM, DOI, DOB, or DOC is buspirone, wherein the buspirone is present between about 1 mg to about 100 mg, or about 1 mg or about 2 mg, or about 3 mg, or about 4 mg, or about 5 mg, or about 6 mg, or about 7 mg, or about 7.5 mg, or about 10 mg, or about 15 mg, or about 22.5 mg, or about 30 mg, or about 37.5 mg, or about 45 mg, or about 52.5 mg, or about 60 mg, or about 1 mg to about 10 mg, or about 5 mg to about 10 mg, or about 10 mg to about 15 mg, or about 15 mg to about 30 mg, or about 30 mg to about 60 mg, or about 60 mg to about 80 mg, or about 80 mg to about 100 mg, and the DOM, DOI, DOB, or DOC is administered between about 0.5 mg and about 15 mg, or about 5 mg. In certain embodiments, such as those described above a disclosed DOM, DOI, DOB, or DOC form is co-administered with a serotonin receptor modulator in the same or in separate compositions. In one embodiment, the DOM, DOI, DOB, or DOC is administered in a modified release formulation such that the subject is effectively pretreated with serotonin receptor modulator prior to release of an effective amount of the psychedelic. Thus, in some embodiments, the serotonin receptor modulator is administered or released from a composition provided herein prior to the administration and/or release of the psychedelic. This allows pretreatment to attenuate activation of the serotonin receptor by the psychedelic. In some embodiments, the serotonin receptor modulator is administered or released from the composition provided herein to pretreat a subject by at least about at about 5 minutes, 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, 1 hour, 1.25 hours, 1.5 hours, 2 hours, or 3 hours prior to the release of the psychedelic. In some embodiments, the serotonin receptor modulator attenuates the activation of the serotonin receptor when the serotonin receptor modulator is used to pretreat at most about 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, or more than 9 hours prior to the release of the psychedelic. In some embodiments, the serotonin receptor modulator attenuates the activation of the serotonin receptor when the serotonin receptor modulator is used to pretreat in a range of about 5 minutes to about 3 hours, about 10 minutes to about 3 hours, about 20 minutes to about 3 hours, about 30 minutes to about 3 hours, about 40 minutes to about 3 hours, about 50 minutes to about 3 hours, about 1 hour to about 3 hours, about 5 minutes to about 2 hours, about 10 minutes to about 2 hours, about 20 minutes to about 2 hours, about 30 minutes to about 2 hours, about 40 minutes to about 2 hours, about 50 minutes to about 2 hours, about 1 hour to about 2 hours, about 5 minutes to about 1 hour, about 10 minutes to about 1 hour, about 20 minutes to about 1 hour, about 30 minutes to about 1 hour, about 40 minutes to about 1 hour, or about 50 minutes to about 1 hour prior to the release of the psychedelic. In a preferred embodiment, the serotonin receptor modulator is administered at about 1 hour to about 3 hours prior to the administration of the psychedelic. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 15 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat between at least 30 minutes prior and 360 minutes prior to the release or administration of the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat between at least 60 minutes prior and 360 minutes prior to the release or administration the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat between at least 90 minutes and 240 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 120 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 180 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 210 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 240 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 270 minutes prior to DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 300 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 330 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the eplivanserin is administered to pretreat at least 360 minutes prior to the DOM, DOI, DOB, or DOC. In some preferred embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein eplivanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat a subject between at least 15 minutes and 360 minutes prior to the administration or release of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 90 minutes prior to DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 120 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 180 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 210 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 240 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 270 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 300 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 330 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the volinanserin is administered to pretreat at least 360 minutes prior to the DOM, DOI, DOB, or DOC. In some preferred embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein volinanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 15 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 90 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 120 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 180 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 210 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 240 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 270 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 300 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 330 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ketanserin is administered to pretreat at least 360 minutes prior to the DOM, DOI, DOB, or DOC. In some preferred embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein ketanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 15 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 30 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 90 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 120 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 180 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 210 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 240 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 270 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 300 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 330 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the ritanserin is administered to pretreat at least 360 minutes prior to the DOM, DOI, DOB, or DOC. In some preferred embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein ritanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 15 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 30 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 90 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 120 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 180 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 210 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 240 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 270 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 300 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 330 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pimavanserin is administered to pretreat at least 360 minutes prior to the DOM, DOI, DOB, or DOC. In some preferred embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein pimavanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 15 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 30 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 90 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 120 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 180 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 210 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 240 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 270 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 300 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 330 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the nelotanserin is administered to pretreat at least 360 minutes prior to the DOM, DOI, DOB, or DOC. In some preferred embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein nelotanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 15 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 30 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 90 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 120 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 180 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 210 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 240 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 270 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 300 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 330 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the pruvanserin is administered to pretreat at least 360 minutes prior to the DOM, DOI, DOB, or DOC. In some preferred embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein pruvanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 15 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 30 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 90 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 120 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 180 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 210 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 240 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 270 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 300 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 330 minutes prior to the DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein the flibanserin is administered to pretreat at least 360 minutes prior to the DOM, DOI, DOB, or DOC. In some preferred embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM, DOI, DOB, or DOC, wherein flibanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of DOM, DOI, DOB, or DOC. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is eplivanserin and, wherein the eplivanserin is administered in about 1 mg to about 40 mg, or about 5 mg to about 10 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic DOM salt and solid forms disclosed in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein wherein the volinanserin is administered in about 1 mg to about 60 mg, or about 5 mg to about 20 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is ketanserin, wherein the ketanserin is administered in about 10 mg to about 80 mg, about 30 mg to about 50 mg, or about 40 mg and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is ritanserin, wherein the ritanserin is administered in about 1 mg to about 40 mg, or about 2.5 mg to about 10 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic DOM salt and solid forms disclosed in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein wherein the pimavanserin is administered in about 1 mg to about 60 mg, or about 17 mg to about 34 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is nelotanserin, wherein the nelotanserin is administered in about 1 mg to about 80 mg, or about 40 mg to about 80 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is pruvanserin, wherein the pruvanserin is administered in about 1 mg to about 40 mg, or about 3 mg to about 10 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is flibanserin, wherein the flibanserin is administered in about 10 mg to about 200 mg, or about 80 mg to about 120 mg, or about 100 mg and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is olanzapine, wherein the olanzapine is administered in about 2.5 mg to about 30 mg, or about 5mg or about 10 mg, or about 20 mg or about 25mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is an extended-release of olanzapine such as ZYPREXA RELPREVV, wherein the extended release olanzapine is administered in about 50 mg to about 450 mg, or about 150 mg or about 210 mg, or about 300 mg or about 405 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is quetiapine, wherein the quetiapine is administered in about 25 mg to about 800 mg, or about 50 mg to about 100 mg, or about 150mg or about 200mg or about 250mg or about 300mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is an extended-release of quetiapine, wherein the extended-release of quetiapine is administered in about 50 mg to about 300 mg, or about 50mg or about 100 mg or about 200 mg, or about 300 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is risperidone, wherein the risperidone is administered in about 0.5mg to about 20mg or about .5mg, or about 1mg, or about 2mg, or about 3mg or about 4mg or about 5mg or about 7.5mg or about 10mg or about 16mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is an extended-release of risperidone including RISPERDAL CONSTA, wherein the extended-release of risperidone is administered in about 12.5 mg, or about 25 mg, or about 37.5 mg, or about 50 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the psychedelic DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is buspirone, wherein the buspirone is present between about 1 mg to about 100 mg, or about 1 mg or about 2 mg, or about 3 mg, or about 4 mg, or about 5 mg, or about 6 mg, or about 7 mg, or about 7.5 mg, or about 10 mg, or about 15 mg, or about 22.5 mg, or about 30 mg, or about 37.5 mg, or about 45 mg, or about 52.5 mg, or about 60 mg, or about 1 mg to about 10 mg, or about 5 mg to about 10 mg, or about 10 mg to about 15 mg, or about 15 mg to about 30 mg, or about 30 mg to about 60 mg, or about 60 mg to about 80 mg, or about 80 mg to about 100 mg, and the DOM salt and solid forms disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein are administered between about 0.5 mg and about 15 mg, or about 5 mg. In certain embodiments, such as those described above a DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is co-administered with a serotonin receptor modulator in the same or in separate compositions. In one embodiment, the serotonin receptor modulator is administered prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein. In one embodiment, the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl forms disclosed herein is administered in a modified release formulation such that the subject is effectively pretreated with serotonin receptor modulator prior to release of an effective amount of the DOM or DOI. In some embodiments the serotonin receptor modulator is part of a single fixed dose formulation that releases serotonin receptor modulator first followed by the DOM or DOI on two different release profiles. In another embodiment the serotonin receptor modulator is administered first as a single dosage and after a length of time, the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein is administered as a second dosage separate from the first dosage. Thus, in some embodiments, the serotonin receptor modulator is administered or released from a composition provided herein prior to the administration and/or release of the psychedelic. This allows pretreatment to attenuate activation of the serotonin receptor by the psychedelic. In some embodiments, the serotonin receptor modulator is administered or released from the composition provided herein to pretreat a subject by at least about at about 5 minutes, 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, 1 hour, 1.25 hours, 1.5 hours, 2 hours, or 3 hours prior to the release of the psychedelic. In some embodiments, the serotonin receptor modulator attenuates the activation of the serotonin receptor when the serotonin receptor modulator is used to pretreat at most about 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, or more than 9 hours prior to the release of the psychedelic. In some embodiments, the serotonin receptor modulator attenuates the activation of the serotonin receptor when the serotonin receptor modulator is used to pretreat in a range of about 5 minutes to about 3 hours, about 10 minutes to about 3 hours, about 20 minutes to about 3 hours, about 30 minutes to about 3 hours, about 40 minutes to about 3 hours, about 50 minutes to about 3 hours, about 1 hour to about 3 hours, about 5 minutes to about 2 hours, about 10 minutes to about 2 hours, about 20 minutes to about 2 hours, about 30 minutes to about 2 hours, about 40 minutes to about 2 hours, about 50 minutes to about 2 hours, about 1 hour to about 2 hours, about 5 minutes to about 1 hour, about 10 minutes to about 1 hour, about 20 minutes to about 1 hour, about 30 minutes to about 1 hour, about 40 minutes to about 1 hour, or about 50 minutes to about 1 hour prior to the release of the psychedelic. In a preferred embodiment, the serotonin receptor modulator is administered at about 1 hour to about 3 hours prior to the administration of the psychedelic. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat between at least 30 minutes prior and 360 minutes prior to the release or administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat between at least 60 minutes prior and 360 minutes prior to the release or administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat between at least 90 minutes and 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 270 minutes prior to DOM. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein eplivanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat a subject between at least 15 minutes and 360 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein volinanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein ketanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 30 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein ritanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 30 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein pimavanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 30 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein nelotanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 30 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein pruvanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 30 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein the flibanserin is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM or DOI, wherein flibanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 30 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein the olanzapine is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM or DOI, wherein olanzapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 30 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein the quetiapine is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM or DOI, wherein quetiapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 30 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein the risperidone is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM or DOI, wherein risperidone is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 15 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 30 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 90 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 120 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 180 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 210 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 240 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 270 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 300 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 330 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein the buspirone is administered to pretreat at least 360 minutes prior to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is buspirone and the psychedelic is DOM or DOI, wherein buspirone is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In certain embodiments, such as those described above, a DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or a DOI HCl form disclosed herein is co-administered with a serotonin receptor modulator in the same or in separate compositions. In one embodiment, the serotonin receptor modulator is administered after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or a DOI HCl form disclosed herein. In one embodiment, the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein is administered in a modified release formulation such that the subject is effectively post-treated with serotonin receptor modulator post to release of an effective amount of the DOM or DOI. In some embodiments, the serotonin receptor modulator is part of a single fixed dose formulation that releases the DOM or DOI first followed by serotonin receptor modulator on two different release profiles. In another embodiment, the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein is administered first as a single dosage and, after a length of time, serotonin receptor modulator is administered as a second dosage separate from the first dosage. Thus, in some embodiments, the serotonin receptor modulator is administered or released from a composition provided herein after the administration and/or release of the psychedelic. This allows post-treatment to attenuate activation of the serotonin receptor by the psychedelic. In some embodiments, the serotonin receptor modulator is administered or released from the composition provided herein to post-treat a subject by at least about at about 5 minutes, 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, 1 hour, 1.25 hours, 1.5 hours, 2 hours, or 3 hours after the release of the psychedelic. In some embodiments, the serotonin receptor modulator attenuates the activation of the serotonin receptor when the serotonin receptor modulator is used to post-treat at most about 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, or more than 9 hours after the release of the psychedelic. In some embodiments, the serotonin receptor modulator attenuates the activation of the serotonin receptor when the serotonin receptor modulator is used to post-treat in a range of about 5 minutes to about 3 hours, about 10 minutes to about 3 hours, about 20 minutes to about 3 hours, about 30 minutes to about 3 hours, about 40 minutes to about 3 hours, about 50 minutes to about 3 hours, about 1 hour to about 3 hours, about 5 minutes to about 2 hours, about 10 minutes to about 2 hours, about 20 minutes to about 2 hours, about 30 minutes to about 2 hours, about 40 minutes to about 2 hours, about 50 minutes to about 2 hours, about 1 hour to about 2 hours, about 5 minutes to about 1 hour, about 10 minutes to about 1 hour, about 20 minutes to about 1 hour, about 30 minutes to about 1 hour, about 40 minutes to about 1 hour, or about 50 minutes to about 1 hour after the release of the psychedelic. In a preferred embodiment, the serotonin receptor modulator is administered at about 1 hour to about 3 hours after the administration of the psychedelic. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 15 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat between at least 30 minutes after and 360 minutes after the release or administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat between at least 60 minutes after and 360 minutes after the release or administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat between at least 90 minutes and 240 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 120 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 180 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 210 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 240 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 270 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 300 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 330 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein the eplivanserin is administered to post-treat at least 360 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM or DOI, wherein eplivanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat a subject between at least 15 minutes and 360 minutes after the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat between at least 30 minutes and 360 minutes after the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 90 minutes after DOM. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 120 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 180 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 210 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 240 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 270 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 300 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 330 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein the volinanserin is administered to post-treat at least 360 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM or DOI, wherein volinanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the ®-MDMA form. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 15 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat between at least 30 minutes and 360 minutes after the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 90 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 120 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 180 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 210 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 240 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 270 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 300 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 330 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein the ketanserin is administered to post-treat at least 360 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM or DOI, wherein ketanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 15 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 30 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 90 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 120 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 180 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 210 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 240 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 270 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 300 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 330 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein the ritanserin is administered to post-treat at least 360 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM or DOI, wherein ritanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 15 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 30 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 90 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 120 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 180 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 210 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 240 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 270 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 300 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 330 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein the pimavanserin is administered to post-treat at least 360 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM or DOI, wherein pimavanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 15 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 30 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 90 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 120 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 180 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 210 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 240 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 270 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 300 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 330 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein the nelotanserin is administered to post-treat at least 360 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM or DOI, wherein nelotanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 15 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 30 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 90 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 120 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 180 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 210 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 240 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 270 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 300 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 330 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein the pruvanserin is administered to post-treat at least 360 minutes after the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM or DOI, wherein pruvanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 15 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 30 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 90 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 120 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 180 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 210 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 240 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 270 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 300 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 330 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 360 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is flibanserin, wherein flibanserin is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 15 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 30 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 90 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 120 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 180 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 210 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 240 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 270 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 300 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 330 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 360 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is olanzapine, wherein olanzapine is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 15 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 30 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 90 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 120 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 180 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 210 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 240 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 270 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 300 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 330 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 360 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is quetiapine, wherein quetiapine is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 15 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 30 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 90 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 120 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 180 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 210 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 240 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 270 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 300 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 330 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 360 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is risperidone, wherein risperidone is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 15 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 30 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 90 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 120 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 180 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 210 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 240 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 270 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 300 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 330 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the serotonin receptor modulator is buspirone, wherein the buspirone is administered to post-treat at least 360 minutes post to the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some preferred embodiments, the serotonin receptor modulator is buspirone, wherein buspirone is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM form disclosed herein, including those described in Table Ex3B, Ex5B, or Ex5D, or the DOI HCl form disclosed herein. In some embodiments, the combination therapy of the present disclosure, comprises administration of a solid form of DOM or DOI, e.g., any of the solid forms of DOM or DOI, as disclosed herein, in combination with a serotonin receptor modulator, as described above. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is eplivanserin, wherein the eplivanserin is administered in about 1 mg to about 40 mg, or about 5 mg to about 10 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is volinanserin, wherein the volinanserin is administered in about 1 mg to about 60 mg, or about 5 mg to about 20 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is ketanserin, wherein the ketanserin is administered in about 10 mg to about 80 mg, about 30 mg to about 50 mg, or about 40 mg and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is ritanserin, wherein the ritanserin is administered in about 1 mg to about 40 mg, or about 2.5 mg to about 10 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator is pimavanserin and the DOM glycolate Form 1 wherein the pimavanserin is administered in about 1 mg to about 60 mg, or about 17 mg to about 34 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is nelotanserin, wherein the nelotanserin is administered in about 1 mg to about 80 mg, or about 40 mg to about 80 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is pruvanserin, wherein the pruvanserin is administered in about 1 mg to about 40 mg, or about 3 mg to about 10 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is flibanserin, wherein the flibanserin is administered in about 10 mg to about 200 mg, or about 80 mg to about 120 mg, or about 100 mg and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is olanzapine, wherein the olanzapine is administered in about 2.5 mg to about 30 mg, or about 5mg or about 10 mg, or about 20 mg or about 25mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is an extended-release of olanzapine such as ZYPREXA RELPREVV, wherein the extended release olanzapine is administered in about 50 mg to about 450 mg, or about 150 mg or about 210 mg, or about 300 mg or about 405 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is quetiapine, wherein the quetiapine is administered in about 25 mg to about 800 mg, or about 50 mg to about 100 mg, or about 150mg or about 200mg or about 250mg or about 300mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is an extended-release of quetiapine, wherein the extended-release of quetiapine is administered in about 50 mg to about 300 mg, or about 50mg or about 100 mg or about 200 mg, or about 300 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is risperidone, wherein the risperidone is administered in about 0.5mg to about 20mg or about.5mg, or about 1mg, or about 2mg, or about 3mg or about 4mg or about 5mg or about 7.5mg or about 10mg or about 16mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is an extended-release of risperidone including RISPERDAL CONSTA, wherein the extended-release of risperidone is administered in about 12.5 mg, or about 25 mg, or about 37.5 mg, or about 50 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM glycolate Form 1 is buspirone, wherein the buspirone is administered between about 1 mg to about 100 mg, or about 1 mg or about 2 mg, or about 3 mg, or about 4 mg, or about 5 mg, or about 6 mg, or about 7 mg, or about 7.5 mg, or about 10 mg, or about 15 mg, or about 22.5 mg, or about 30 mg, or about 37.5 mg, or about 45 mg, or about 52.5 mg, or about 60 mg, or about 1 mg to about 10 mg, or about 5 mg to about 10 mg, or about 10 mg to about 15 mg, or about 15 mg to about 30 mg, or about 30 mg to about 60 mg, or about 60 mg to about 80 mg, or about 80 mg to about 100 mg, and the DOM glycolate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is eplivanserin, wherein the eplivanserin is administered in about 1 mg to about 40 mg, or about 5 mg to about 10 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is volinanserin, wherein the volinanserin is administered in about 1 mg to about 60 mg, or about 5 mg to about 20 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is ketanserin, wherein the ketanserin is administered in about 10 mg to about 80 mg, about 30 mg to about 50 mg, or about 40 mg and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is ritanserin, wherein the ritanserin is administered in about 1 mg to about 40 mg, or about 2.5 mg to about 10 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator is pimavanserin and the DOM L- malate Form 1 wherein the pimavanserin is administered in about 1 mg to about 60 mg, or about 17 mg to about 34 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is nelotanserin, wherein the nelotanserin is administered in about 1 mg to about 80 mg, or about 40 mg to about 80 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is pruvanserin, wherein the pruvanserin is administered in about 1 mg to about 40 mg, or about 3 mg to about 10 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is flibanserin, wherein the flibanserin is administered in about 10 mg to about 200 mg, or about 80 mg to about 120 mg, or about 100 mg and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is olanzapine, wherein the olanzapine is administered in about 2.5 mg to about 30 mg, or about 5mg or about 10 mg, or about 20 mg or about 25mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is an extended-release of olanzapine such as ZYPREXA RELPREVV, wherein the extended release olanzapine is administered in about 50 mg to about 450 mg, or about 150 mg or about 210 mg, or about 300 mg or about 405 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is quetiapine, wherein the quetiapine is administered in about 25 mg to about 800 mg, or about 50 mg to about 100 mg, or about 150mg or about 200mg or about 250mg or about 300mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is an extended-release of quetiapine, wherein the extended-release of quetiapine is administered in about 50 mg to about 300 mg, or about 50mg or about 100 mg or about 200 mg, or about 300 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is risperidone, wherein the risperidone is administered in about 0.5mg to about 20mg or about.5mg, or about 1mg, or about 2mg, or about 3mg or about 4mg or about 5mg or about 7.5mg or about 10mg or about 16mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is an extended-release of risperidone including RISPERDAL CONSTA, wherein the extended-release of risperidone is administered in about 12.5 mg, or about 25 mg, or about 37.5 mg, or about 50 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator for use with the DOM L-malate Form 1 is buspirone, wherein the buspirone is administered between about 1 mg to about 100 mg, or about 1 mg or about 2 mg, or about 3 mg, or about 4 mg, or about 5 mg, or about 6 mg, or about 7 mg, or about 7.5 mg, or about 10 mg, or about 15 mg, or about 22.5 mg, or about 30 mg, or about 37.5 mg, or about 45 mg, or about 52.5 mg, or about 60 mg, or about 1 mg to about 10 mg, or about 5 mg to about 10 mg, or about 10 mg to about 15 mg, or about 15 mg to about 30 mg, or about 30 mg to about 60 mg, or about 60 mg to about 80 mg, or about 80 mg to about 100 mg, and the DOM L-malate Form 1 is administered between about 0.5 mg and about 15 mg, or about 5 mg. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat between at least 30 minutes prior and 360 minutes prior to the release or administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat between at least 60 minutes prior and 360 minutes prior to the release or administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat between at least 90 minutes and 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 270 minutes prior to DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein eplivanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat a subject between at least 15 minutes and 360 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein volinanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein ketanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 30 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein ritanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 30 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein pimavanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 30 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein nelotanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 30 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein pruvanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 30 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein the flibanserin is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM glycolate Form 1, wherein flibanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 30 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein the olanzapine is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM glycolate Form 1, wherein olanzapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 30 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein the risperidone is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM glycolate Form 1, wherein risperidone is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 15 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 30 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 90 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 120 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 180 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 210 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 240 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 270 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 300 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 330 minutes prior to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein the quetiapine is administered to pretreat at least 360 minutes prior to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM glycolate Form 1, wherein quetiapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat between at least 30 minutes prior and 360 minutes prior to the release or administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L- malate Form 1, wherein the eplivanserin is administered to pretreat between at least 60 minutes prior and 360 minutes prior to the release or administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat between at least 90 minutes and 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat at least 120 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L- malate Form 1, wherein the eplivanserin is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat at least 270 minutes prior to DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat at least 300 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein eplivanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat a subject between at least 15 minutes and 360 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat at least 120 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L- malate Form 1, wherein the volinanserin is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L- malate Form 1, wherein the volinanserin is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat at least 300 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L- malate Form 1, wherein the volinanserin is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein volinanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 120 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L- malate Form 1, wherein the ketanserin is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 300 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to pretreat at least 360 minutes prior to the DOM L- malate Form 1. In some preferred embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein ketanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 30 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L- malate Form 1, wherein the ritanserin is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 120 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 300 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein ritanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat at least 30 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat at least 120 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L- malate Form 1, wherein the pimavanserin is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L- malate Form 1, wherein the pimavanserin is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat at least 300 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L- malate Form 1, wherein the pimavanserin is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein pimavanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 30 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 120 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L- malate Form 1, wherein the nelotanserin is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L- malate Form 1, wherein the nelotanserin is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 300 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein nelotanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 30 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 120 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 300 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L- malate Form 1, wherein the pruvanserin is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein pruvanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 30 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L- malate Form 1, wherein the flibanserin is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 120 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 300 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein the flibanserin is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is flibanserin and the psychedelic is DOM L-malate Form 1, wherein flibanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat at least 30 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat at least 120 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L- malate Form 1, wherein the olanzapine is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L- malate Form 1, wherein the olanzapine is administered to pretreat at least 300 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein the olanzapine is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L- malate Form 1, wherein the olanzapine is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is olanzapine and the psychedelic is DOM L-malate Form 1, wherein olanzapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat at least 30 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat at least 120 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L- malate Form 1, wherein the risperidone is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L- malate Form 1, wherein the risperidone is administered to pretreat at least 300 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein the risperidone is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L- malate Form 1, wherein the risperidone is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is risperidone and the psychedelic is DOM L-malate Form 1, wherein risperidone is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 15 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 30 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L- malate Form 1, wherein the quetiapine is administered to pretreat at least 90 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 120 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 180 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 210 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 240 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 270 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 300 minutes prior to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 330 minutes prior to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein the quetiapine is administered to pretreat at least 360 minutes prior to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is quetiapine and the psychedelic is DOM L-malate Form 1, wherein quetiapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 15 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat between at least 30 minutes after and 360 minutes after the release or administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat between at least 60 minutes after and 360 minutes after the release or administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat between at least 90 minutes and 240 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 120 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 180 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 210 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 240 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 270 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 300 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 330 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein the eplivanserin is administered to post-treat at least 360 minutes after the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM glycolate Form 1, wherein eplivanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat a subject between at least 15 minutes and 360 minutes after the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post- treat between at least 30 minutes and 360 minutes after the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 90 minutes after DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 120 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 180 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 210 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 240 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 270 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 300 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 330 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein the volinanserin is administered to post-treat at least 360 minutes after the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM glycolate Form 1, wherein volinanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 15 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat between at least 30 minutes and 360 minutes after the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 90 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 120 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 180 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 210 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 240 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 270 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 300 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 330 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein the ketanserin is administered to post-treat at least 360 minutes after the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM glycolate Form 1, wherein ketanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 15 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 30 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 90 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 120 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 180 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 210 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post- treat at least 240 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 270 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 300 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post- treat at least 330 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein the ritanserin is administered to post-treat at least 360 minutes after the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM glycolate Form 1, wherein ritanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 15 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 30 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 90 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 120 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 180 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 210 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 240 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 270 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 300 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 330 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein the pimavanserin is administered to post-treat at least 360 minutes after the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM glycolate Form 1, wherein pimavanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 15 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 30 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 90 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 120 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 180 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 210 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 240 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 270 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 300 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 330 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein the nelotanserin is administered to post-treat at least 360 minutes after the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM glycolate Form 1, wherein nelotanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 15 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 30 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 90 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 120 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 180 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 210 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 240 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 270 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 300 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 330 minutes after the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein the pruvanserin is administered to post-treat at least 360 minutes after the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM glycolate Form 1, wherein pruvanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 15 minutes post to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 30 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 90 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 120 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 150 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 180 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 210 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 240 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 270 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 300 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 330 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 360 minutes post to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is flibanserin, wherein flibanserin is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 15 minutes post to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 30 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 90 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 120 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 150 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 180 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 210 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 240 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 270 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 300 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 330 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 360 minutes post to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is olanzapine, wherein olanzapine is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 15 minutes post to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 30 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 90 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 120 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 150 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 180 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 210 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 240 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 270 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 300 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 330 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 360 minutes post to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is quetiapine, wherein quetiapine is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 15 minutes post to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 30 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 90 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 120 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 150 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 180 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 210 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 240 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 270 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 300 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 330 minutes post to the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 360 minutes post to the DOM glycolate Form 1. In some preferred embodiments, the serotonin receptor modulator is risperidone, wherein risperidone is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM glycolate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat at least 15 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat between at least 30 minutes after and 360 minutes after the release or administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat between at least 60 minutes after and 360 minutes after the release or administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat between at least 90 minutes and 240 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat at least 120 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat at least 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat at least 180 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L- malate Form 1, wherein the eplivanserin is administered to post-treat at least 210 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat at least 240 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat at least 270 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat at least 300 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat at least 330 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein the eplivanserin is administered to post-treat at least 360 minutes after the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is DOM L-malate Form 1, wherein eplivanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat a subject between at least 15 minutes and 360 minutes after the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post- treat between at least 30 minutes and 360 minutes after the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat at least 90 minutes after DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat at least 120 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat at least 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat at least 180 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L- malate Form 1, wherein the volinanserin is administered to post-treat at least 210 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat at least 240 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L- malate Form 1, wherein the volinanserin is administered to post-treat at least 270 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat at least 300 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L- malate Form 1, wherein the volinanserin is administered to post-treat at least 330 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein the volinanserin is administered to post-treat at least 360 minutes after the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is DOM L-malate Form 1, wherein volinanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat at least 15 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat between at least 30 minutes and 360 minutes after the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat at least 90 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat at least 120 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat at least 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat at least 180 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L- malate Form 1, wherein the ketanserin is administered to post-treat at least 210 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post- treat at least 240 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat at least 270 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat at least 300 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat at least 330 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein the ketanserin is administered to post-treat at least 360 minutes after the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is DOM L-malate Form 1, wherein ketanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat at least 15 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat at least 30 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L- malate Form 1, wherein the ritanserin is administered to post-treat at least 90 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat at least 120 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat at least 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L- malate Form 1, wherein the ritanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat at least 180 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat at least 210 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post- treat at least 240 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat at least 270 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat at least 300 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post- treat at least 330 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein the ritanserin is administered to post-treat at least 360 minutes after the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is DOM L-malate Form 1, wherein ritanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat at least 15 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat at least 30 minutes after the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat at least 90 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat at least 120 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat at least 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat at least 180 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L- malate Form 1, wherein the pimavanserin is administered to post-treat at least 210 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat at least 240 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L- malate Form 1, wherein the pimavanserin is administered to post-treat at least 270 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat at least 300 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L- malate Form 1, wherein the pimavanserin is administered to post-treat at least 330 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein the pimavanserin is administered to post-treat at least 360 minutes after the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is DOM L-malate Form 1, wherein pimavanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 15 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 30 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 90 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 120 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 180 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L- malate Form 1, wherein the nelotanserin is administered to post-treat at least 210 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 240 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L- malate Form 1, wherein the nelotanserin is administered to post-treat at least 270 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 300 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 330 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein the nelotanserin is administered to post-treat at least 360 minutes after the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is DOM L-malate Form 1, wherein nelotanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat at least 15 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat at least 30 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat between at least 60 minutes and 240 minutes after the administration or release of the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat at least 90 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat at least 120 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L- malate Form 1, wherein the pruvanserin is administered to post-treat at least 150 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat between about 15 minutes and about 150 minutes after the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat at least 180 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat at least 210 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat at least 240 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat at least 270 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L- malate Form 1, wherein the pruvanserin is administered to post-treat at least 300 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein the pruvanserin is administered to post-treat at least 330 minutes after the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L- malate Form 1, wherein the pruvanserin is administered to post-treat at least 360 minutes after the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is DOM L-malate Form 1, wherein pruvanserin is administered to post-treat between about 60 minutes and about 180 minutes after the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 15 minutes post to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 30 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 90 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 120 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 150 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 180 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 210 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 240 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 270 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 300 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 330 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is flibanserin, wherein the flibanserin is administered to post-treat at least 360 minutes post to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is flibanserin, wherein flibanserin is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 15 minutes post to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 30 minutes post to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 90 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 120 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 150 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 180 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 210 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 240 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 270 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 300 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 330 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is olanzapine, wherein the olanzapine is administered to post-treat at least 360 minutes post to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is olanzapine, wherein olanzapine is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 15 minutes post to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 30 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 90 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 120 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 150 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 180 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 210 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 240 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 270 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 300 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 330 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is quetiapine, wherein the quetiapine is administered to post-treat at least 360 minutes post to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is quetiapine, wherein quetiapine is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 15 minutes post to the administration of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 30 minutes post to the DOM L- malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat between at least 60 minutes and 240 minutes post to the administration or release of the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 90 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 120 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 150 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat between about 15 minutes and about 150 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 180 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 210 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 240 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 270 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 300 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 330 minutes post to the DOM L-malate Form 1. In some embodiments, the serotonin receptor modulator is risperidone, wherein the risperidone is administered to post-treat at least 360 minutes post to the DOM L-malate Form 1. In some preferred embodiments, the serotonin receptor modulator is risperidone, wherein risperidone is administered to post-treat between about 60 minutes and about 180 minutes post to the administration of the DOM L-malate Form 1. VII. Examples Example 1 - Salt Screen DOM, DOI, DOB, and DOC are characterized to evaluate its physical properties. The evaluation is performed by X-ray powder diffraction (XRPD), polarized light microscopy (PLM), differential scanning calorimetry (DSC), thermogravimetry (TG), dynamic vapor sorption/desorption (DVS), and/or solubility testing in organic solvents, water, and mixed solvent systems. XRPD data is used to assess crystallinity. PLM data is used to evaluate crystallinity and particle size/morphology. DSC data is used to evaluate melting point, thermal stability, and crystalline form conversion. TG data is used to evaluate if the free base is a solvate or hydrate, and to evaluate thermal stability. DVS data is used to evaluate hygroscopicity of the free base and if hydrates can be formed at high relative humidity. About 10 to 15 solvents are selected from the list below, based on their properties (polarity, dielectric constant and dipole moment). Table Ex1 - Solvents

The information obtained is used for designing the subsequent salt screen. The salt screen is performed by reacting the free base with pharmaceutically acceptable acids under various conditions in attempts to generate crystalline salts. Pharmaceutically acceptable acids that may be used are listed in Table 1^^^6SHFLILF^DFLGV^DUH^VHOHFWHG^EDVHG^RQ^WKH^S.D^RI^WKH^IUHH^ base, and typically 15 to 20 acids are selected. Experiments are performed using 0.5 molar equivalent, 1 molar equivalent and/or 2 molar equivalents of the acid. In some embodiments, the acid is not hydrochloric acid. Solvent systems for the salt crystallization experiments are selected based on the solubility of the free base and the selected acid. Solvents are used as a single solvent or as solvent mixtures, some containing water. The techniques that are used for salt crystallization are chosen based on the solvent selected and properties of the free base. The following techniques (or combination of techniques) may be used for salt crystallization: Free base and acid are dissolved in a solvent or mixture of solvents, and the solvents are evaporated at different rates (slow evaporation or fast evaporation) and at different temperatures (ambient or elevated). Free base and acid are dissolved in a solvent or mixture of solvents (at ambient temperature or an elevated temperature), and the final solution is cooled to a sub-ambient temperature (between -78 °C to 15 °C). The cooling method can be a fast cooling (by plunging the sample into an ice bath or a dry ice/acetone bath), or slow cooling. The solids formed will be recovered by filtration and dried (air dried or vacuum dried). Free base and acid are dissolved in a solvent or mixture of solvents, and an antisolvent is added to precipitate the salt. The solids formed will be recovered by filtration and dried (air dried or vacuum dried). Free base and acid are added to a solvent or mixture of solvents, where one or both components are not fully dissolved. The slurry is agitated at different temperatures for a number of days. The solids formed will be recovered by filtration and dried (air dried or vacuum dried). The same experiment can be also performed in solvent systems where the solvents are not miscible. Free base and acid are milled together (by mechanical milling or by mortar and pestle), with a drop of solvent, or without any solvent. Free base and acid are melted together, and cooled to various temperatures using various cooling rates. If an amorphous form of a salt is obtained, the amorphous salt will be exposed to elevated humidity, or elevated temperature (or combination of both), or solvent vapors at various temperatures to form crystalline salts. The stoichiometric ratio of acid to DOM, DOI, DOB, or DOC is confirmed by ¹H

NMR, HPLC, or both as is known to those of ordinary skill in the art. The salts obtained are analyzed by XRPD to determine if they are crystalline and, if so, by DSC to see the melting point and by TG to see if they are hydrated/solvated, and by 1H NMR spectroscopy to ensure chemical integrLW\^^.)^ZDWHU^WLWUDWLRQ^LV^SHUIRUPHG^RQ^VDOWV^WKDW^DUH^ hydrated. DVS analysis is performed to evaluate hygroscopicity of the salt and if hydrated form is present. Example 2 - Polymorph Screen The active pharmaceutical ingredient (API), which may be a free base or a salt, is characterized to evaluate its physical properties. The evaluation is performed by X-ray powder diffraction (XRPD), polarized light microscopy (PLM), differential scanning calorimetry (DSC), thermogravimetry (TG), dynamic vapor sorption/desorption (DVS), and/or solubility testing in organic solvents, water, and mixed solvent systems. XRPD data is used to assess crystallinity. PLM data is used to evaluate crystallinity and particle size/morphology. DSC data is used to evaluate melting point, thermal stability, and crystalline form conversion. TG data is used to evaluate if the API is a solvate or hydrate, and to evaluate thermal stability. DVS data is used to evaluate hygroscopicity of the API and if hydrates can be formed at high relative humidity. About 10 to 15 solvents may be selected from Table Ex1, based on their properties (polarity, dielectric constant and dipole moment). The information obtained is used for designing the subsequent polymorph screen. Solvents are used as a single solvent or as solvent mixtures, some containing water. The techniques used for the polymorph screen are chosen based on the solvent selected and properties of the API. The following techniques (or a combination of techniques) may be used for the polymorph screening: API is dissolved in a solvent or mixture of solvents, and the solvents are evaporated at different rates (slow evaporation or fast evaporation) and at different temperatures (ambient or elevated). API is dissolved in a solvent or mixture of solvents (at ambient temperature or an elevated temperature), and the final solution is cooled (between -78 °C to 20 °C). The cooling method can be a fast cooling (by plunging the sample to an ice bath or a dry ice/acetone bath), or slow cooling. The solids formed will be recovered by filtration and dried (air dried or vacuum dried). API is dissolved in a solvent or mixture of solvents, and an antisolvent is added to precipitate the salt. The solids formed will be recovered by filtration and dried (air dried or vacuum dried). API is added to a solvent or mixture of solvents, where the API is not fully dissolved. The slurry will be agitated at different temperatures for a number of days. The solids formed will be recovered by filtration and (air dried or vacuum dried). API is milled (by mechanical milling or by mortar and pestle), with a drop of solvent, or without any solvent. API is melted and cooled (at different cooling rates, fast and slow, and cooled to different temperatures) to obtain solids. API is suspended m a solvent or mixture of solvents, and the slurry is placed in a heating/cooling cycle for multiple cycles. The remaining solids after the final cooling cycle will be filtered and (air dried or vacuum dried).

API is processed to obtain an amorphous form (by melting, milling, solvent evaporation, spray drying or lyophilization). The amorphous form will then be exposed to elevated humidity (or elevated temperature, or combination thereof), or to solvent vapors for extended period of days.

API is exposed to elevated humidity (or elevated temperature, or combination thereof), or to solvent vapors for extended period of days.

Two or more polymorphs of the API are mixed in a solvent or solvent systems (some solvent mixtures containing variable amount of water) to obtain a slurry, and the slurry will be agitated (at various temperatures) for an extended period of time (days). The solvent system used can be pre-saturated, with the API. The final solids will be filtered and dried (air dried or vacuum dried).

API is heated to a specific temperature and cooled (at ambient conditions or in a dry box).

The solids obtained are analyzed by XRPD to determine if they are crystalline and, if so, by DSC to see the melting point and by TG to see if they are hydrated/solvated, and by *H NMR spectroscopy to ensure chemical integrity, KF water titration is performed on forms that are hydrated. DVS analysis is performed to evaluate hygroscopicity of the form and if hydrated form is present. In particular variable temperature analyses, including variable temperature XRPD, are performed to assess the stability of each physical form as well as its crystallinity.

Differential scanning calorimetry (DSC) thermograms are obtained using a DSC Q 100 (TA Instruments, New Castle, DE). The temperature axis and cell constant of the DSC cell are calibrated with indium (10 mg, 99.9% pure, melting point 156.6°C, heat of fusion 28.4 J/g). Samples (2.0 - 5.0 mg) are weighed in aluminum pans on an analytical balance. .Aluminum pans without lids are used for the analysis. The samples are equilibrated at 25°C and heated to 250 - 300 °C at. a. heating rate of 10°C/min under continuous nitrogen flow. TG analysis of the samples is performed with a Q 50(TA Instruments, N ew Castle, DE). Samples (2.0 --- 5.0 mg) are analyzed in open aluminum pans under a nitrogen flow (50 mL/min) at 25°C to 210°C with a heating rate of 10°C/min. The sample for moisture analysis is allowed to dry at 25 °C for up to 4 hours under a stream of dry nitrogen. The relative humidity is then increased stepwise from 10 to 90% relative humidity (adsorption scan) allowing the sample to equilibrate for a maximum of four hours before weighing and moving on to the next step. The desorption scan is measured from 85 to 0% relative humidity with the same equilibration time. The sample is then dried under a stream of dry nitrogen at 80 °C for 2 hours or until no weight loss is observed.

X-ray powder diffraction data are collected using a Miniflex Tabletop XRD system (Rigaku/MSC, The Woodlands, TX) from 5° to 45° 29 with steps of 0.1°, and the measuring time is 1.0 second/step. All samples are ground to similar size before exposure to radiation. The powder samples are illuminated using CuKa radiation (λ = 1.54056A) at 30 kV and 15 mA.

Variable temperature XRPD data are collected using a Huber Imaging Plate Guinier Camera 670 employing Ni-filtered Cu Kα1 radiation (λ = 1.5405981 A) produced at 40 kV and 20 mA by a Philips PW1120/00 generator fitted with a Huber long fine-focus tube PW2273/20 and a Huber Guinier Monochromator Series 611/15. The original powder is packed into a Lindemann capillary (Hilgenberg, Germany) with an internal diameter of 1 mm and a wall thickness of 0.01 mm. The sample is heated at an average rate of 5 Kmin^-1 using a Huber High Temperature Controller HTC 9634 unit with the capillary rotation device 670.2. The temperature is held constant at selected intervals for 10 mm while the sample is exposed to X-rays and multiple scans were recorded. A 20-range of 4.00 - 100.0° is used. with a step size of 0.005° 29.

In certain embodiments wherein the solid form is a solvate, such as a hydrate, the DSC thermogram reveals endothermic transitions. In accordance with the observed DSC transitions, TGA analysis indicates stages of weight change corresponding to desolvation or dehydration and/or melting of the sample. In the case of hydrates, these results are in harmony with Karl Fisher titration data, which indicate the water content of the sample.

The moisture sorption profile of a sample can be generated to assess the stability of a. solid form is stable over a range of relative humidities. In certain embodiments, the change in moisture content over 10.0 to 95.0 % relative humidity is small. In other embodiments the change in moisture content over 10.0 to 95.0 % relative humidity is reversible.

In certain embodiments, the XRPD pattern of a sample of solid form indicates that the sample has a well-defined crystal structure and a high degree of crystallinity. Example 3 - Salt Screen and Characterization of DOM (Racemate) A salt screen of DOM was performed. The free base form was mixed with various acids under various conditions in attempts to generate crystalline salts. Exemplary acids used included L-aspartic, adipic, benzenesulfonic, fumaric, gentisic, glutamic, glutaric, glycolic, HCl, 1-hydroxy-2-napthoic, L-malic, maleic, malonic, methanesulfonic, mucic, phosphoric, sulfuric, succinic, L-tartaric, and p-toluenesulfonic acids. Solubilities of DOM in a few solvents were estimated. The experiments were carried out by adding the test solvent in aliquots to weighed portions of solid. Whether dissolution had occurred was judged by visual inspection after addition of each solvent aliquot. The results are shown in Table Ex3A. Solubility numbers were calculated by dividing the weight of the sample by the total amount of solvent used to dissolve the sample. The actual solubilities may be greater than the numbers calculated because the solvent aliquots used may have been too large or because of slow dissolution rates. The solubility number is expressed as “less than” if dissolution did not occur during the experiment. The solubility number is expressed as “greater than or equal to” if dissolution occurred on addition of the first solvent aliquot. All solubility measurements were carried out at room temperature unless noted otherwise. Table Ex3A. Estimated Solubilities of DOM

DOM was mixed with various acids under various conditions in attempts to generate crystalline salts. Samples generated and analyzed are listed in Table Ex3B. All experiments were carried out using 1 molar equivalent of acid (unless noted otherwise). Table Ex3B. Salt Screen of DOM

&^ ^FRRO^^(^ ^HYDSRUDWLRQ^^,6^ ^LQVXIILFLHQW^VROLGV^^16^ ^QR^VROLGV^^ 3^ ^SUHFLSLWDWLRQ^^6(^ ^VORZ^HYDSRUDWLRQ^^6/^ ^VOXUU\^^57^ ^URRP^WHPSHUDWXUH^ /&^ ^ORZ^FU\VWDOOLQLW\^^1&^ ^QRQ-crystalline; 32^ ^SUHIHUUHG^RULHQWDWLRQ; SNV^ ^SHDNV All of the salts were characterized by X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC), thermogravimetric analysis (TG), and ¹H nuclear magnetic resonance (NMR) spectroscopy. The characterization results are summarized in Table Ex3C. In cases where there was a weight loss by TG but no organic solvents observed in the NMR spectrum, it was assumed the weight loss was due to water. The amount of water (moles of water per mole of salt) is reported in the table with the TG results. Samples made using hydrochloric, phosphoric, and sulfuric acid were also analyzed by ion chromatography because stoichiometry of those salts could not be determined by ¹H NMR spectroscopy.¹H NMR spectra of salt samples exhibit down field chemical shifts of the protons adjacent to the amine in DOM, indicating salt formation. Most of the materials appear to be unsolvated based on the TG data, and in most cases the DSC curves exhibit a melting endotherm above 100 °C. The majority of the materials appear to be salts by ¹H NMR spectroscopy, having a stoichiometry of either 1:1 or 2:1 DOM:acid. One sample, the tosylate salt, has a stoichiometry of 1:0.7 DOM:acid. The nature of this material is unknown. It may be a 1:1 salt with an additional molar equivalent of free DOM (cocrystal of salt and free DOM) as well as additional free acid. Additional studies, such as single crystal structure determination, would be needed to confirm the nature of this material. Table Ex3C. Characterization of Unique Materials from Salt Screen

Several salts were selected for hygroscopicity evaluation at 75% RH and water solubility estimation. Samples were selected for this testing if the thermal data showed a sharp melting endotherm above 100 °C. In cases where multiple crystalline forms of a salt were obtained, only one form was selected for this testing. The hygroscopicity evaluation experiments were carried out by exposing about 2-3 mg of each material to 75% RH at room temperature for 24 hours. The samples were then observed visually for flowability. With the exception of the adipate, glutamate, and glutarate salts, all materials remained free flowing and did not become sticky. The solubility experiments were carried out by adding the test solvent in 100 μL aliquots to weighed portions of solid, about 2-3 mg. Whether dissolution had occurred was judged by visual inspection after addition of each solvent aliquot. Solubility numbers were calculated by dividing the weight of the sample by the total amount of solvent used to dissolve the sample. With the exception of the xinafoate salt, which had a water solubility of below 1 mg/mL, all salts exhibited a water solubility of 2 mg/mL or greater. The highest water solubility was observed with the L-malate and succinate salts which were 27 and 24 mg/mL, respectively. Three of the salts, the glycolate, hydrochloride, and L-malate, were chosen for characterization by dynamic vapor sorption (DVS) and short term physical stability at both 40 °C/75% RH and ambient/93% RH (FIGs.85-87). Those salts were chosen for additional testing because each has a high melting point (above 150 °C), is reasonably soluble in water (~10 mg/mL or greater), remained free flowing after exposure to 75% RH for 1 day, and was able to be made from two different experiments. All of them became sticky after exposure to both temperature/humidity conditions. The HCl salt became a wet paste at 40 °C/75% RH. XRPD analysis of each salt after exposure to the conditions showed that the crystalline forms did not change, although a couple of small unknown peaks were observed in the XRPD pattern of the L- malate salt after exposure to 40 °C/75% RH. The nature of these peaks is unknown, but they are believed to be due to a metastable crystalline form because re-analysis of the sample after room temperature storage showed the unknown peaks to no longer be present. The summary of the characterization results is shown in Table Ex3D. Table Ex3D. Summary of Characterization Results

Example 4 - Preparation of DOM Salts Preparation of DOM Adipate Dissolved 20.1 mg DOM in 1 mL acetone. Added 14.0 mg adipic acid to a separate vial dissolved in 1 mL acetone. Combined vials, precipitation was initially observed then went clear. The sample was stirred magnetically in a refrigerator at 2°C for 3 days. The sample was vacuum filtered and air dried at room temperature. Preparation of DOM Besylate Dissolved 19.6 mg DOM in 1 mL acetone. Added 14.8 mg benzenesulfonic acid to a separate vial dissolved in 100 μL acetone. Combined vials, no precipitation observed. The sample was stirred magnetically in a refrigerator at 2°C overnight, then stirred maginetically in a freezer at -15°C for 5 days. The sample was vacuum filtered and air dried at room temperature. Preparation of DOM Glutamate Added 19.8 mg of DOM and 13.8 mg L-glutamic acid to a grinding cup containing one metal ball. Added 10μL 1:1 water:EtOH to cup. Cup placed on retsch mill to grind for 30 minutes at 100% power. Sample was air dried at room temperature. Preparation of DOM Glutarate 2 Dissolved 20.4 mg DOM in 1 mL THF. Added 12.5 mg glutaric acid to a separate vial dissolved in 100 μL THF. Combined vials, no precipitation observed. The sample was stirred magnetically at room temperature overnight, then stirred maginetically in a refrigerator at 2°C for overnight. The sample was then stirred magnetically in a freezer at - 15°C for 6 days. The sample was vacuum filtered and air dried at room temperature. Preparation of DOM Glycolate Dissolved 20.2 mg DOM in 1 mL acetone. Added 7.5 mg glycolic acid to a separate vial dissolved in 100 μL acetone. Combined vials, no precipitation observed. The sample was stirred magnetically in a refrigerator at 2°C for 4 days. The sample was vacuum filtered and air dried at room temperature. Preparation of DOM Hydrochloride Dissolved 20.3 mg DOM in 1 mL acetone. Added 95.6 μL HCL in ether to vial. Precipitation observed. The sample was stirred magnetically at room temperature for 4 days. The sample was vacuum filtered and air dried at room temperature. Preparation of DOM L-Malate Dissolved 19.5 mg DOM in 1 mL acetone. Added 12.8 mg L-malic acid to a separate vial dissolved in 100 μL acetone. Combined vials, precipitation observed. The sample was stirred magnetically at room temperature for 4 days. The sample was vacuum filtered and air dried at room temperature. Preparation of DOM Mucate Added 19.9 mg of DOM and 9.7 mg mucic acid to a grinding cup containing one metal ball. Added 10μL 1:1 water:EtOH to cup. Cup placed on retsch mill to grind for 30 minutes at 100% power. Sample was air dried at room temperature. Preparation of DOM Phosphate Dissolved 20.1 mg DOM in 1 mL acetone. Added 10.6 mg phosphoric acid to a separate vial dissolved in 100 μL acetone. Combined vials, precipitation observed. The sample was stirred magnetically at room temperature for 4 days. The sample was vacuum filtered and air dried at room temperature. Preparation of DOM Succinate Dissolved 19.9 mg DOM in 1 mL acetone. Added 11.3 mg succinic acid to a separate vial dissolved in 1 mL acetone. Combined vials, no precipitation observed. The sample was stirred magnetically in a refrigerator at 2°C for 4 days. The sample was vacuum filtered and air dried at room temperature. Preparation of DOM Tartrate 1 Dissolved 20.3 mg DOM in 1 mL acetone. Added 14.1 mg L-tartaric acid to a separate vial dissolved in 1 mL acetone. Combined vials, precipitation observed. The sample was stirred magnetically at room temperature for 4 days. The sample was vacuum filtered and air dried at room temperature. Preparation of DOM Xinafoate Dissolved 19.9 mg DOM in 1 mL acetone. Added 18.1 mg 1-hydroxy-2-napthoic acid to a separate vial dissolved in 200 μL acetone. Combined vials, no precipitation observed. The sample was stirred magnetically in a freezer at -15°C overnight. The sample was vacuum filtered and air dried at room temperature. Example 5 - Polymorph Screen of DOM Glycolate and DOM L-malate Solubility measurements of DOM glycolate and L-malate salts Solubilities of each salt in a few solvents were estimated. The experiments were carried out by adding the test solvent in aliquots to weighed portions of solid. Whether dissolution had occurred was judged by visual inspection after addition of each solvent aliquot. The results are shown in Table Ex5A. Solubility numbers were calculated by dividing the weight of the sample by the total amount of solvent used to dissolve the sample. The actual solubilities may be greater than the numbers calculated because of the use of solvent aliquots that were too large or because of slow dissolution rates. The solubility number is expressed as “less than” if dissolution did not occur during the experiment. All solubility measurements were carried out at room temperature unless noted otherwise. Table Ex5A. Estimated Solubilities of DOM Glycolate and L-Malate Salts

Polymorph screen of DOM glycolate Samples of DOM glycolate were mixed with various solvents under various conditions in attempts to generate crystalline materials. The experiments are summarized in Table Ex5B. Table Ex5B. Polymorph Screen of DOM Glycolate

Only one crystalline form was identified, designated as glycolate form 1. Glycolate form

5 1 is unsolvated and was identified in the salt screen (Example 3). Non-crystalline material was prepared in-situ via a DSC experiment and the glass transition temperature was determined to be 18.1 °C. The non-crystalline material was heat cycled on the DSC and in the second cycle it was apparent that it had already began to crystallize, demonstrating the propensity for it to crystallize quickly. This was further confirmed by an attempt to prepare non-crystalline glycolate salt via.

10 melt-quench which resulted in a mixture of glycolate form 1 and non-crystalline material.

Table Ex5C. Cycling DSC Results for the DOM Glycolate Salt

Polymorph screening of DOM L-malate

Samples of DOM L-malate were mixed with various solvents under various conditions in

15 attempts to generate crystalline materials. The experiments are summarized, in Table Ex5D. Table Ex5D Polymorph Screen of DOM L-Malate

Three new crystalline patterns were identified, designated as L-malate forms 1, 2, and 3. L-malate form 1 is unsolvated and was identified in the salt screen (Example 3). L-malate form 2 was only obtained as a mixture with L-malate form 1. It was obtained from an evaporation experiment involving water. An attempt to remake L-malate form 2 resulted in L-malate form 3. L-malate form 3 was obtained from two experiments involving water; an evaporation and slurry experiment. An overlay plot of the XRPD patterns is shown in FIG. 80. Both L-malate forms 2 and 3 are believed to be hydrates. Non-crystalline material was prepared via lyophilization from water and the glass transition temperature was determined to be 15.9 °C. When exposed to elevated temperature and/or humidity, non-crystalline L-malate salt crystallized to a mixture of L-malate forms 1 and 3. The non-crystalline L-malate salt was analyzed by modulated DSC to determine the glass transition temperature. The data is summarized in Table Ex5E. A glass transition event was observed at approximately 15.9 °C. The endotherm with signal maximum around 74.4 °C is likely due to evolution of residual water. Table Ex5E. Modulated DSC Results for the Non-crystalline L-malate Salt

Preparation of DOM Glycolate Form 1 Dissolved 1.000 g of DOM in 70 mL of acetone at room temperature. Dissolved 0.363 g of glycolic acid in 3 mL of acetone. The glycolic acid solution was slowly added to the solution of freebase, and no precipitate formed. The solution was stirred magnetically at room temperature for 3 days, during which time, crystallization occured. The slurry was vacuum filtered and the resulting white solid was allowed to air dry at room temperature to give 1.03 g of glycolate salt form 1. Preparation of DOM L-Malate Form 1 Dissolved 1.001 g of DOM in 75 mL of acetone at room temperature. Dissolved 0.641 g of L-malic acid in 3 mL of acetone. The L-malic acid solution was slowly added to the solution of freebase, resulting in a precipitate. The slurry was stirred magnetically at room temperature for 3 days. The slurry was vacuum filtered and the resulting white solid was allowed to air dry at room temperature to give 0.3 g of L-malate salt form 1. Example 6 - Crystallization and Characterization of DOM 101.3 mg of DOM was placed into a 20 mL glass vial. Added 2 mL of water and stirred magnetically at 60 °C. The solid in the slurry became an oil upon heating. Added 1 mL water about every 5 minutes until the oil dissolved (additional 12 mL water added). The heat was turned off and the sample was allowed to cool to room temperature. The next day white solid was observed. The solid was recovered by vacuum filtration and allowed to air-dry in a room temperature fume hood. The sample was characterized by a variety of techniques. The results are shown in Table Ex6. It may be a hydrate; the TG curve shows a 10.1% weight loss up to 90 °C which corresponds to approximately 1.3 moles of water per mole of DOM. The endotherm at approximately 109 °C in the DSC curve is likely due to melting. The material is slightly hygroscopic. The DVS curve exhibits a weight gain of approximately 0.5% in the range from 5-95% RH. The weight loss on the desorption step was approximately 0.9%, leaving the material with a net weight loss of 0.4% after the experiment. The material recovered after the DVS experiment was analyzed by XRPD and the pattern was unique (FIG.73). The crystals are fiber-like in morphology. The NMR spectrum is consistent with the compound structure. The doublet of doublets in the NMR spectrum between 0.91 and 0.99 ppm (assigned to the methyl group adjacent to the amine) suggests that DOM exists as a rotational isomer in solution. Table Ex6. Characterization of DOM

Summary DOM (4-methyl-2,5-dimethoxyamphetamine) was crystallized from water. The resulting crystalline material was designated as DOM Form A. It may be a mono-hydrate which, when heated, dehydrates and subsequently melts at approximately 109 °C. It is slightly hygroscopic and converted to a new crystalline form during the hygroscopicity testing experiment (dynamic vapor sorption). The crystals of DOM form A are fiber-like in morphology. Example 7 - Crystallization and Characterization of DOI HCl 50.2mg of DOI HCl was suspended in 1mL of EtOH. The slurry was stirred magnetically on a hot plate set to 60 °C. The solids dissolved. The vial was removed from the plate and allowed to cool to room temperature. No solids had formed by the next day. The sample was placed in a refrigerator at approximately 5 °C. Solids were observed the next day. The sample was centrifuged, the mother liquor decanted, and the solids allowed to air dry for about 1 hour. XRPD spectra was as shown in FIG.79. Example 8 - General Experimental Information X-ray Powder Diffraction (XRPD) A Rigaku SmartLab X-Ray Diffractometer was configured in Bragg–Brentano reflection geometry equipped with a beam stop and knife edge to reduce incident beam and air scatter. Data collection parameters are shown in the following table. Table Ex8. PXRD Data Collection Parameters

Differential Scanning Calorimetry (DSC) DSC analyses were carried out using a TA Instruments Q2500 Discovery Series instrument. The instrument temperature calibration was performed using indium. The DSC cell was kept under a nitrogen purge of about 50 mL per minute during each analysis. The sample was placed in a standard, crimped, aluminum pan and was heated from approximately 25 °C to 350 °C at a rate of 10 °C per minute.

Thermogravimetric (TG) Analysis

The TG analysis was carried out using a TA Instruments Q5500 Discovery Series instrument. The instrument balance was calibrated using class M weights and the temperature calibration was performed using alumel. The nitrogen purge was ~40 mL per minute at the balance and ~60 mL per minute at the furnace. Each sample was placed into a pre-tared platinum pan and heated from approximately 25 °C to 350 °C at a rate of 10 °C per minute.

Dynamic Vapor Sorption (DVS) Analysis

DVS analysis was carried out using a TA Instruments Q5000 Dynamic Vapor Sorption analyzer. The instrument was calibrated with standard weights and a sodium bromide standard for humidity. Approximately 10-25 mg of sample was loaded into a metal- coated quartz pan for analysis. The sample was analyzed at 25 °C with a maximum equilibration time of one hour in 10% relative humidity (RH) steps from 5 to 95% RH (adsorption cycle) and from 95 to 5% RH (desorption cycle). The movement from one step to the next occurred either after satisfying the equilibrium criterion of 0.01% weight change or, if the equilibrium criterion was not met, after one hour. The percent weight change values were calculated using Microsoft Excel®.

Optical Microscopy

Optical microscopy experiments were carried out on a Leica DM 2500 P compound microscope. Images were captured using a. PAXcam3 camera. Magnification is displayed on each image.

Nuclear Magnetic Resonance (NMR) Spectroscopy

The 1 H NMR spectra were acquired on a Bruker Avance II 400 spectrometer. Samples were prepared by dissolving material in CD3OD. The solutions were filtered and placed into individual 5-mm NMR tubes for subsequent spectral acquisition. The temperature controlled (295K) 1H NMR spectra, acquired on the Avance II 400 utilized a 5- mm cryoprobe operating at an observing frequency of 400.18 MHz.

Ion Chromatography (IC)

The data was acquired on an Agilent 1100 HPLC with a Shimadzu conductivity detector and a polymeric anion exchange resin column. The mobile phase was a. sodium carbonate/sodium hydrogen carbonate solution. Each sample was dissolved in water at a concentration of 2 mg/mL and injected using a liquid pump and autosampler. The results are in w/w %. Prior to analysis, the system was calibrated using standards prepared from NIST traceable standard solutions.

Infrared (FT-IR) Spectroscopy

IR spectra were acquired using a Thermo Scientific model iS50 Fourier- transform (FI) IR spectrophotometer equipped with a deuterated triglycine sulfate (DTGS) detector, a potassium bromide (KBr) beamsplitter, and a Polaris'™ long-life IR source. A diamond attenuated total reflectance (ATR) sampling accessory with a spectral range of 4000 cm^-1 to 400 cm^-1 was used. Each spectrum was the result of 128 co-added scans acquired at 2 cm^-1 resolution. A single beam background scan of air was acquired before the sample scan, allowing presentation of the spectra in log 1/R units. Wavelength calibration was performed using polystyrene. OMNIC v9.11 software package (Thermo-Nicolet) was used to acquire, process, and evaluate the spectral data.

Example 9 - Evaluation of Metabolic Stability in Human Liver Microsomes

Microsomal Assay: Human liver microsomes (20 mg/mL, ) are obtained, p- nicotinamide adenine dinucleotide phosphate, reduced form (NADPH), magnesium chloride (MgCh), and dimethyl sulfoxide (DMSO) were purchased from Sigma- Aldrich.

Determination of Metabolic Stability: 7.5 mM stock preparations of test compounds of the disclosed compounds are prepared in a suitable solvent, such as DMSO. The 7.5 mM stock preparations are diluted to 12.5-50 pM in acetonitrile (ACN). The 20 mg/mL human liver microsomes are diluted to 0.625 mg/mL in 0. 1 M potassium phosphate buffer, pH 7.4, containing 3 mM MgCh. The diluted microsomes are added to wells of a 96-well deep-well polypropylene plate in triplicate. A 10 pL aliquot of the 12.5-50 μM test compound is added to the microsomes and the mixture is pre- warmed for 10 minutes. Reactions are initiated by addition of pre- warmed NADPH solution. The final reaction volume is 0.5 mL and contains 4.0 mg/mL human liver microsomes, 0.25 uM test compound, and 2 mM NADPH in 0.1 M potassium phosphate buffer, pH 7.4, and 3 mM MgCh. The reaction mixtures are incubated at 37 °C, and 50 pL aliquots are removed at 0, 5, 10, 20, and 30 minutes and added to shallow-well 96-well plates which contain 50 pL of ice-cold ACN (acetonitrile) with internal standard to stop the reactions. The plates are stored at 4 °C for 20 minutes after which 100 pL of water is added to the wells of the plate before centrifugation to pellet precipitated proteins. Supernatants are transferred to another 96-well plate and analyzed for amounts of parent remaining by LC-MS/MS using an Applied

Bio-systems API 4000 mass spectrometer. The same procedure is followed for the positive control, 7-ethoxycoumarin (1 p.M). Testing is done in triplicate.

Data analy sis: The in vitro T/,s for test compounds are calculated from the slopes of the linear regression of % parent remaining (In) vs incubation time relationship. in vitro Tv = 0.693/k k [slope of linear regression of % parent remaining (In) vs incubation time]

The apparent intrinsic clearance is calculated using the following equation:

CL_int (mL/min/kg) = (0.693 / in vitro T) (Incubation Volume / mg of microsomes) (45 mg microsomes / gram of liver) (20 gm of liver / kg b.w.)

Data analysis is performed using Microsoft Excel Software.

In these experiments, values equal to or more than a 15% increase in half-life are considered to be a significant difference if the apparent intrinsic clearance ratio (salt or solid form/ comparator solid form of DOM, DOI, DOB, or DOC) is >1.15 or <0.85, then there is considered to be significant differentiation.

Example 10 - Oral Bioavailability in Rats

Pharmacokinetics of test articles following a single intravenous or oral administration in rats: A pharmacokinetic (PK) study is performed in three male Sprague-Dawley (SD) rats following intravenous (IV) and oral (PO) administration of a compound disclosed herein. Test compounds are measured in plasma.

A detailed description of the in vivo methods:

Rat Strain

Rats used m these studies are supplied by Charles River (Margate UK) and are specific pathogen free. The strain of rats is Sprague Dawley. Male rats are 175 - 225g on receipt and are allowed to acclimatise for 5-7 days.

.Animal Housing Rats are group housed in sterilised individual ventilated cages that expose the animals at all times to HEPA filtered sterile air. Animals will have free access to food and water (sterile) and will have sterile aspen chip bedding (at least once weekly). The room temperature is 22°C +/- 1°C, with a relative humidity of 60% and maximum background noise of 56dB. Rats are exposed to 12 hour light/dark cycles. Treatment The test articles are administered in a suitable dose volume for intravenous (IV) or (PO) for oral routes of administration. Single IV/PO dose pharmacokinetics study in rats Each test article is administered as a single IV bolus (via a lateral tail-vein) or a single oral gavage in cohorts of 3 rats per route. Following dose administrations, a 100μL whole blood sample (EDTA) is collected via the tail-vein at time-points described in Table 1. The blood is centrifuged to separate plasma. Approximately 40μL of plasma is dispensed per time- point, per rat, in a 96 well plate and frozen until analysis. Bioanalysis is carried out on plasma samples. Dose formulation Samples Dose formulation samples were diluted in two steps with 50:50 (v/v) methanol/water to an appropriate concentration, then diluted 10:90 (v/v) with control matrix to match to the calibration standard in plasma. Sample Extraction procedure Calibration and QC standards, incurred samples, blank matrix and dose formulation samples were extracted by protein precipitation, via the addition of a bespoke acetonitrile (ACN)-based Internal Standard (IS) solution, containing several compounds and including Metoprolol and Rosuvastatin, both of which were monitored for during analysis. Following centrifugation, a 40 μL aliquot of supernatant was diluted by the addition of 80 μL water. The prepared sample extracts were analysed by LC-MS/MS. In one embodiment, the oral bioavailability of a disclosed crystalline solid form is superior to an amorphous or known crystalline form. Example 11 - Biological assays and methods Head-Twitch Response (HTR). The head-twitch response assay is performed as is known to those of skill in the art using both male and female C57BL/6J mice (2 per treatment). The mice are obtained and were approximately 8 weeks old at the time of the experiments. Compounds were administered via intraperitoneal injection (5 rnL/kg) using 0.9% saline as the vehicle. As a positive control, 5-MeO-DMT fumarate (2:1 amine/acid) was utilized. Behavior was videotaped, later scored by two blinded observers, and the results were averaged (Pearson correlation coefficient = 0.93).

Serotonin and Opioid Receptor Functional Assays. Functional assay screens at 5- HT and opioid receptors are performed in parallel using the same compound dilutions and 384-well format high-throughput assay platforms. Assays assess activity at all human isoforms of the receptors, except where noted for the mouse 5-HT2A receptor. Receptor constructs in pcDNA vectors were generated, from the Presto-Tango GPCR library with minor modifications. All compounds were serially diluted in drug buffer (BBSS, 20 mM HEPES, pH 7.4 supplemented with 0.1% bovine serum albumin and 0.01% ascorbic acid) and dispensed into 384-well assay plates using a FLIPR^TETRA (Molecular Devices). Every plate included a positive control such as 5-HT (for all 5-HT receptors), DADLE (DOR), salvinorin A (KOR), and DAMGO (MOR). For measurements of 5-HT2A, 5-HT2B, and 5- HT2C Gq-mediated calcium flux function, HEK Flp-In 293 T-Rex stable cell lines (Invitrogen) were loaded with Fluo.4 dye for one hour, stimulated with compounds and read for baseline (0-10 seconds) and peak fold-over-basal fluorescence (5 minutes) at 25°C on the FLIPR^TETRA. For measurement of 5-HT6 and 5-HT7a functional assays, Gs-mediated cAMP accumulation was detected using the split-luciferase GloSensor assay in HEKT cells measuring luminescence on a Microbeta. Trilux (Perkin Elmer) with a .15 mm drug incubation at 25°C. For 5-HT1A, 5-HT1B, 5-HT1F, MOR, KOR, and DOR functional assays, Gi/o-mediated cAMP inhibition was measured using the split-luciferase GloSensor assay in HEKT cells, conducted similarly as above, but in combination with either 0.3 μM isoproterenol (5-HT1 A, 5-HT1B, 5-HT1F) or 1 μM forskolin (MOR, KOR, and DOR) to stimulate endogenous cAMP accumulation. For measurement of 5-HT1D, 5-HT1E, 5-HT4, and 5-HT5A functional assays, P-arrestin2 recruitment was measured by the Tango assay utilizing HTLA cells expressing TEV fused-P-arrestin2, as described previously with minor modifications. Data for all assays were plotted and non-linear regression was performed using “log(agonist) vs. response” in Graphpad Prism to yield Emax and ECso parameter estimates.

5HT_2A Sensor Assays, HEK293T (ATCC) 5HT2A sensor stable line (slight1.3s) is generated via lentiviral transduction of HIV-EFla-sLightl .3 and propagated from a. single colony. Lentivirus is produced using 2^nd generation lentiviral plasmids pHIV -EF1α - sLightl.3, pHCMV-G, and pCMV-deltaR8.2.

For the screening of the compounds, sLightl.3s cells are plated in 96-well plates at a density of 4000024-hours prior to imaging. On the day of imaging, compounds in DMSO are diluted from the 100 mM stock preparations to working concentrations of 1 mM, 100 mM and 1 μM with a DMSO concentration of 1%. Immediately prior to imaging, cells growing in DMEM (Gibco) are washed 2x with HESS (Gibco) and in agonist mode 180μL of HBSS or in antagonist mode 160μL of HBSS is added to each well after the final wash. For agonist mode, images are taken before and after the addition of the 20 μL compound working preparation into the wells containing 180μL HESS. This produces final compound, concentrations of 100 mM, 10 mM and 100 nM with a DMSO concentration of 0.1%. For antagonist mode, images are taken before and after addition of 20μL of 900nM 5-HT and again after 20μL of the compound working preparation to produce final concentrations of 100nM for 5HT and 100mM, lOmM and 100nM for the compounds with a DMSO concentration of 0. 1%. Each compound is tested in triplicate (3 wells) for each concentration ( 100mM, 10mM and 1 OOnM), Additionally, within each plate, 100nM 5HT and 0. 1% DMSO controls are also imaged.

Imaging is performed using the Leica DMi8 inverted microscope with a 40x objective using the FITC preset with an excitation of 460nm and emission of 512-542nm. For each well, the cellular membrane where the 5HT2A sensor is targeted is autofocused using the adaptive focus controls and 5 images from different regions within the well were taken with each image processed from a 2x2 binning.

For data, processing, the membranes from each image are segmented and analyzed using a custom algorithm written in MATF AB producing a. single raw fluorescence intensity- value. For each well the 5 raw fluorescence intensity values generated from the 5 images are averaged and the change in fluorescence intensity (dFF) is calculated as: dFF - (F _sat - F_apo)/ F_apo

For both agonist and antagonist modes, the fluorescence intensity values before compound addition in FIBSS only are used as the F_apo values while the fluorescence intensity values after compound addition are used as the F_sat values. For agonist mode, data are as percent activation relative to 5HT, where 0 is the average of the DMSO wells and 100 is the average of the 100 μM 5HT wells. For antagonist mode, the inactivation score is calculated as: ,QDFWLYDWLRQ^VFRUH^ ^^G)))^Compound+5HT) - dFF(5HT))/dFF(5HT) Plasticity Effects: Treatment of rat embryonic cortical neurons with compounds disclosed herein is evaluated for increased dendritic arbor complexity at 6 days in vitro (DIV6) as measured by Sholl analysis. The effect of the present compounds on dendritic growth can be determined to be 5-HT2A-dependent, if pretreatment with ketanserin—a 5- HT2A antagonist— inhibits their effects. In addition to promoting dendritic growth, the present compounds also are evaluated for increased dendritic spine density to a comparable extent as ibogaine in mature cortical cultures (DIV20). The effects of the compounds on cortical dendritic spine dynamics in vivo using transcranial 2-photon imaging is assessed. First, spines are imaged on specific dendritic loci defined by their relation to blood vessel and dendritic architectures. Next, the animals are systemically administered vehicle, a compound of the present invention, or a positive control compound. After 24 h, the same dendritic segments are re-imaged, and the number of spines gained or lost is quantified. Examples of the presently disclosed compounds increase spine formation in mouse primary sensory cortex, suggesting that the present compounds support neuronal plasticity. As increased cortical structural plasticity in the anterior parts of the brain mediates the sustained (>24 h) antidepressant- like effects of ketamine and play a role in the therapeutic effects of 5-HT2A agonists, the impact of the present compounds on forced swim test (FST) behavior is evaluated. First, a pretest is used to induce a depressive phenotype. Compounds are administered 24 h after the pre-test, and the FST is performed 24 h and 7 d post compound administration. Effective compounds of the invention, like ketamine, significantly reduced immobility 24 h after administration. Dendritogenesis Assays. Compounds disclosed herein are evaluated for their ability to increase dendritic arbor complexity in cultures of cortical neurons using a phenotypic assay. Following treatment, neurons are fixed and visualized using an antibody against MAP2 — a cytoskeletal protein localized to the somatodendritic compartment of neurons. Sholl analysis is then performed, and the maximum number of crossings (Nmax) was used as a quantitative metric of dendritic arbor complexity. For statistical comparisons between specific compounds, the raw Nmax values are compared. Percent efficacies are determined by setting the Nmax values for the vehicle (DMSO) and positive (ketamine) controls equal to 0% and 100%, respectively.

Animals. For the dendritogenesis experiments, timed pregnant Sprague Dawley rats are obtained. For the head-twitch response assay, male and female C57BL/6J mice are obtained.

Dendritogenesis - Shod Analysis. Dendritogenesis experiments are performed following a previously published methods with slight modifications. Neurons are plated in 96-well format (200 μL of media per well) at a density of approximately 15,000 cells/well in Neurobasal (Life Technologies) containing 1% penicillin-streptomycin, 10% heat-inactivated fetal bovine serum, and 0.5 mM glutamine. After 24 h, the medium is replaced, with Neurobasal containing lx B27 supplement (Life Technologies), 1% penicillin-streptomycin, 0.5 mM glutamine, and. 12.5 pM glutamate. After 3 days in vitro (DIV3), the cells are treated with compounds. All compounds tested in the dendritogenesis assays are treated at 10 pM. Stock preparations of the compounds in DMSO are first diluted 100-fold in Neurobasal before an additional 10-fold dilution into each well (total dilution = 1: 1000; 0.1% DMSO concentration). Treatments are randomized. After 1 h, the media, is removed and replaced with new Neurobasal media, containing lx B27 supplement, 1% penicillin- streptomycin, 0.5 mM glutamine, and 12,5 mM glutamate. The cells are allowed to grow for an additional 71 h. At that time, neurons are fixed by removing 80% of the media, and replacing it with a volume of 4% aqueous paraformaldehyde (Alfa Aesar) equal to 50% of the working volume of the well. Then, the cells are incubated at room temperature for 20 min before the fixative is aspirated and each well washed twice with DPBS. Cells are permeabilized using 0.2% Triton X-100 (ThermoFisher) in DPBS for 20 minutes at room temperature without shaking. Plates are blocked with antibody diluting buffer (ADB) containing 2% bovine serum albumin (BSA) in DPBS for 1 h at room temperature. Then, plates are incubated overnight at 4°C with gentle shaking in ADB containing a chicken anti- MAP2 antibody (1 : 10,000; EnCor, CPCA-MAP2). The next day, plates are washed three times with DPBS and once with 2% ADB in DPBS. Plates are incubated for 1 h at room temperature in ADB containing an anti-chicken IgG secondary/ antibody conjugated to Alexa Fluor 488 (Life Technologies, 1 : 500) and washed five times with DPBS. After the final wash, 100 μL of DPBS is added per well and imaged on an Imag eXpress Micro XL High- Content Screening System (Molecular Devices, Sunnyvale, CA) with a 20x objective. Images are analyzed using Image.) Fiji (version 1.51 W). First, images corresponding to each treatment are sorted into individual folders that are then blinded for data analysis. Plate controls (both positive and negative) are used to ensure that the assay is working properly as well as to visually determine appropriate numerical values for brightness/ contrast and thresholding to be applied universally to the remainder of the randomized images. Next, the brightness/ contrast settings are applied, and approximately 1-2 individual pyramidal-like neurons per image (i.e., no bipolar neurons) are selected using the rectangular selection tool and saved as separate files. Neurons are selected, that do not overlap extensively with other cells or extend far beyond the field of view.

In Vivo Spine Dynamics Male and female Thyl- GFP-M line mice (n = 5 per condition) are purchased from The Jackson Laboratory (JAX #007788) and maintained. In vivo transcramal two-photon imaging and data analysis are performed as previously described. Briefly, mice are anesthetized with an intraperitoneal (i.p.) injection of a mixture of ketamine (87 mg/kg) and xylazine (8,7 mg/kg). A small region of the exposed skull is manually thinned down to 20-30 pm for optical access. Spines on apical dendrites in mouse primary sensory cortices are imaged using a Bruker Ultima IV two-photon microscope equipped with an Olympus water-immersion objective (40x, NA ^::: 0.8) and a Ti: Sapphire laser (Spectra-Physics Mai-Tai, excitation wavelength 920 nm). Images are taken at a zoom of 4.0 (pixel size 0.143 x 0.143 pm) and Z-step size of 0.7 pm. The mice receive an i.p. injection (injection volume ≡ 5 mL/kg) of a disclosed compound immediately after they recover from anesthesia given prior to the first imaging session. The animals are re-imaged 24 h after drug administration. Dendritic spine dynamics were analyzed using ImageJ. Spine formation and elimination were quantified as percentages of spine number on day 0.

Forced Swim Test (FST). Male C57/BL6J mice (9-10 weeks old at time of experiment) are obtained. After 1 week in the vivarium each mouse is handled for approximately 1 minute by the experimenter for 3 consecutive days leading up to the first FST. .All experiments are carried out by the same experimenter who performs handling. During the FST, mice undergo a 6 min swim session in a. clear Plexiglas cylinder 40 cm tail, 20 cm in diameter, and filled with 30 cm of 24 ± 1°C water. Fresh water is used for every mouse. After handling and habituation to the experimenter, drug-naive mice first undergo a pretest swam to more reliably induce a depressive phenotype in the subsequent FST sessions. Immobility scores for all mice are determined after the pre-test and mice are randomly assigned to treatment groups to generate groups with similar average immobility scores to be used for the following two FST sessions. The next day, the animals receive intraperitoneal injections of experimental compounds (20 mg/kg), a positive control (ketamine, 3 mg/kg), or vehicle (saline). The animals were subjected to the FST 30 mins after injection and then returned to their home cages. All FSTs are performed between the hours of 8 am and 1 pm. Experiments are video-recorded, and manually scored offline. Immobility time — defined as passive floating or remaining motionless with no activity other than that needed to keep the mouse’s head above water — is scored for the last 4 min of the 6 min trial.

Statistical analysis. Treatments are randomized, and data are analyzed by experimenters blinded to treatment conditions. Statistical analyses are performed using GraphPad Prism (version 8. 1.2). The specific tests are F-statistics and degrees of freedom. All comparisons are planned prior to performing each experiment. For dendritogenesis experiments a one way ANOVA with Dunnett’s post hoc test is deemed most appropriate. Ketamine was included as a positive control to ensure that the assay is working properly.

Akohol Use Disorder Model: To assess the anti-addictive potential of the present compounds, an alcohol drinking paradigm that models heaw alcohol use and binge drinking behavior in humans is employed. Using a. 2-bottle choice setup (20% ethanol (v/v), EtOH vs. water, H2O), mice are subjected to repeated cycles of binge drinking and withdrawal over the course of 7 weeks.

This schedule results in heaw EtOH consumption, binge drinking-like behavior, and generates blood alcohol content equivalent to that of human subjects suffering from alcohol use disorder (AUD ). Next, compounds of the disclosure are administered via intraperitoneal injection 3 h prior to a drinking session, and EtOH and H2O consumption is monitored. Effective compounds of the disclosure robustly reduce binge drinking during the first 4 h, decreasing EtOH consumption. With exemplary compounds, consumption of ethanol is lower for at least two days following administration with no effect on water intake. Efficacy in this assay suggests the present compounds are useful for the treatment of AUD. EQUIVALENTS In view of the many possible embodiments to which the principles of the present disclosure may be applied, it should be recognized that the illustrated embodiments are only preferred examples and should not be taken as limiting the scope of the present disclosure. Rather, the scope is defined by the following claims. We therefore claim as our invention all that comes within the scope and spirit of these claims.

Claims

CLAIMS What is claimed is:

1. A solid form of DOM, DOI, DOB, or DOC .

2. The solid form of claim 1 , wherein the solid form is a solid form of DOM.

3. The compound of claim 1 , wherein the solid form of DOM is a. salt of DOM.

4. The compound of claim 1, wherein the salt of DOM is a crystalline salt.

5. The compound of claim 1 , wherein the solid form of DOM glycolate Form 1 is a crystalline polymorph of DOM glycolate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 10.1 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

6. The compound of claim 1 , wherein the solid form of DOM glycolate Form 1 is a crystalline polymorph of DOM glycolate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 10.1 °2θ, 15. 1 °2θ, 20.2 °2θ, and 25.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

7. The compound of claim 1 , wherein the solid form of DOM glycolate Form 1 is a. crystalline polymorph of DOM glycolate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 15.1 °2θ, and 20.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

8. The compound of claim 1 , wherein the solid form of DOM glycolate Form 1 is a. crystalline polymorph of DOM glycolate Form 1 characterized by any combination of the XRPD peaks set forth in Table 12 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

9. The compound of claim 1, wherein the solid form of DOM glycolate Form 1 is a crystalline polymorph of DOM glycolate Form 1 characterized by a XRPD diffractogram substantially similar to that shown in FIG. 8.

10. The compound of claim 1 , wherein the solid form of DOM glycolate Form 1 is a. crystalline polymorph of DOM glycolate Form 1 characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 36.

11. The compound of claim 1, wherein the solid form of DOM glycolate Form 1 is a crystalline polymorph of DOM glycolate Form I characterized by a TGA profile is substantially similar to that shown in FIG. 37.

12. The compound of claim 1 , wherein the solid form of DOM glycolate Form 1 is a. crystalline polymorph of DOM glycolate Form 1 characterized by a DSC profile is substantially similar to that shown in FIG. 37.

13. The compound of claim 1, wherein the solid form of DOM L-malate Form 1 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.2 °2θ, 12.6 °2θ, and 15.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

14. The compound of claim 1, wherein the solid form of DOM L-malate Form 1 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.2 °2θ, 12.6 °2θ, 15.2 °2θ, 16.6 °2θ, and 24.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

15. The compound of claim 1, wherein the solid form of DOM L-malate Form 1 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 4.2 °2θ, and 16.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

16. The compound of claim 1, wherein the solid form of DOM L-malate Form 1 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 4.2 °2θ, 16.6 °2θ, 24.7 °2θ, and 22.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

17. The compound of claim 1, wherein the solid form of DOM L-malate Form 1 is a crystalline polymorph of DOM L-malate characterized by any combination of the XRPD peaks set forth in Table 33 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

18. The compound of claim 1 , wherein the solid form of DOM L-malate Form 1 is a crystalline polymorph of DOM L-malate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 11.

19. The compound of claim 1, wherein the solid form of DOM L-malate Form 1 is a crystalline polymorph of DOM L-malate characterized by a ( ¹H NMR spectrum substantially similar to that shown in FIG. 42.

20. The compound of claim 1 , wherein the solid form of DOM L-malate Form 1 is a crystalline polymorph of DOM L-malate characterized by a TGA profile is substantially similar to that shown in FIG. 43.

21. The compound of claim 1, wherein the solid form of DOM L-malate Form 1 is a crystalline polymorph of DOM L-malate characterized by a DSC profile is substantially similar to that shown in FIG. 43.

22. The compound of claim 1, wherein the mixture of solid forms of DOM L-malate Forms 1 and 2 are characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

23. The compound of claim 1, wherein the mixture of solid forms of DOM L-malate Forms 1 and 2 are characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 13.2 °2θ, 14.4 °2θ. 14.9 °2θ. and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

24. The compound of claim 1, wherein the mixture of solid forms of DOM L-malate Forms 1 and 2 are characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, and 24.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation).

25. The compound of claim 1 , wherein the mixture of solid forms of DOM L-malate Forms 1 and 2 are characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ. 16.6 °2θ, and 2L4 ^:°2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

26. The compound of claim 1 , wherein the mixture of solid forms of DOM L-malate Forms 1 and 2 are characterized by any combination of the XRPD peaks set forth in Table 34 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

27. The compound of claim 1, wherein the mixture of the solid forms of DOM L-malate

Forms 1 and 2 are characterized by a XRPD diffractogram substantially similar to that shown in FIG. 77.

28. The compound of claim 1 , wherein the solid form of DOM L-malate Form 2 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

29. The compound of claim 1 , wherein the solid form of DOM L-malate Form 2 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 13.2 °2θ, 14.4 °2θ, 14.9 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

30. The compound of claim 1, wherein the solid form of DOM L-malate Form 2 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, and 24.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

31. The compound of claim 1, wherein the solid form of DOM L-malate Form 2 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 25.0 °2θ, and 26.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

32. The compound of claim 1, wherein the solid form of DOM L-malate Form 2 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 25.0 °2θ, 26.1 °2θ, 14.9 °2θ, and 23.3 °2θ (.±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

33. The compound of claim 1, wherein the solid form of DOM L-malate Form 2 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 15.9 °2θ, 24.5 °2θ, 25.0 °2θ, 26.1 °2θ, 14.9 °2θ. 23.3 °2θ. 20.6 °2θ, 15.4 °2θ. and 20. ± 20 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

34. The compound of claim 1, wherein the solid form of DOM L-malate Form 3 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.9 °2θ, 11.8 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

35. The compound of claim 1, wherein the solid form of DOM L-malate Form 3 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2θ, 4.3 °2θ, 5.9 °2θ, 11.8 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

36. The compound of claim 1, wherein the solid form of DOM L-malate Form 3 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.9 °2θ, 23.7 °2θ, and 11.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

37. The compound of claim 1, wherein the solid form of DOM L-malate Form 3 is a crystalline polymorph of DOM L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.9 °2θ, 23.7 °2θ, 11.8 °2θ, 13.8 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

38. The compound of claim 1, wherein the solid form of DOM L-malate Form 3 is a crystalline polymorph of DOM L-malate characterized by any combination of the XRPD peaks set forth in Table 35 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

39. The compound of claim 1, wherein the solid form of DOM L-malate Form 3 is a crystalline polymorph of DOM L-malate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 78.

40. The compound of claim 1, wherein the solid form of DOM L-aspartate is a crystalline polymorph of DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.8 °2θ, 11.3 °2θ, and 12.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

41. The compound of claim 1 , wherein the solid form of DOM L-aspartate is a. crystalline polymorph of DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.8 °2θ, 7.6 °2θ, 11.3 °2θ, 12.4 °2θ, and 15.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

42. The compound of claim 1 , wherein the solid form of DOM L-aspartate is a. crystalline polymorph of DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.8 °2θ, 11.3 °2θ, and 21.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation).

43. The compound of claim 1 , wherein the solid form of DOM L-aspartate is a. crystalline polymorph of DOM L-aspartate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.8 °2θ, 11.3 °2θ, 11.8 °2θ, 21.4 °2θ, and 21.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

44. The compound of claim 1, wherein the solid form of DOM L-aspartate is a crystalline polymorph of DOM L-aspartate characterized by any combination of the XRPD peaks set forth in Table 2 (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation).

45. The compound of claim 1, wherein the solid form of DOM L-aspartate is a crystalline polymorph of DOM L-aspartate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 1.

46. The compound of claim 1, wherein the solid form of DOM adipate is a crystalline polymorph of DOM adipate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.4 °2θ, 12.8 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation).

47. The compound of claim 1, wherein the solid form of DOM adipate is a crystalline polymorph of DOM adipate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.4 °2θ, 12.8 °2θ, 15.1 °2θ, 16.5 °2θ, and 17.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

48. The compound of claim 1 , wherein the solid form of DOM adipate is a. crystalline polymorph of DOM adipate characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2θ, 22.5 °2θ, and 23.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

49. The compound of claim 1, wherein the solid form of DOM adipate is a crystalline polymorph of DOM adipate characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2θ, 16.5 °2θ, 22.0 °2θ, 22.5 °2θ, and 23.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

50. The compound of claim 1, wherein the solid form of DOM adipate is a crystalline polymorph of DOM adipate characterized by any combination of the XRPD peaks set forth in Table 3 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

51. The compound of claim 1, wherein the solid form of DOM adipate is a crystalline poly morph of DOM adipate characterized by a XRPD diffractogram substantially similar to that sho wn in FIG. 2.

52. The compound of claim 1, wherein the solid form of DOM adipate is a crystalline polymorph of DOM adipate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 24.

53. The compound of claim 1, wherein the solid form of DOM adipate is a crystalline polymorph of DOM adipate characterized by a TGA profile is substantially similar to that shown in FIG. 25.

54. The compound of claim 1, wherein the solid form of DOM adipate is a crystalline polymorph of DOM adipate characterized by a DSC profile is substantially similar to that shown in FIG. 25.

55. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.5 °2θ, 9.1 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

56. The compound of claim 1 , wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.5 °2θ, 9.1 °2θ, 10.6 °2θ, 11.0 °2θ, and 17.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

57. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.0 °2θ, 18.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

58. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.1 °2θ, 11.0 °2θ, 16.2 °2θ, 18.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

59. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by any combination of the XRPD peaks set forth in Table 4 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

60. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.1 °2θ, 19.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

61. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.1 °2θ, 11.0 °2θ, 18.2 °2θ, 19.2 °2θ, and 20.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

62. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by any combination of the XRPD peaks set forth in Table 5 (.±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

63. The compound of claim 1 , wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 3.

64. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 62.

65. The compound of claim 1 , wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 26.

66. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenesulfonate characterized by a TGA profile is substantially similar to that shown in FIG. 27.

67. The compound of claim 1, wherein the solid form of DOM benzenesulfonate is a crystalline polymorph of DOM benzenes ulfonate characterized by a DSC profile is substantially similar to that shown in FIG. 27.

68. The compound of claim 1, wherein the solid form of DOM fumarate Form 1 is a crystalline polymorph of DOM fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2θ, 9.8 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

69. The compound of claim 1, wherein the solid form of DOM fumarate Form 1 is a crystalline polymorph of DOM fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2θ, 9.8 °2θ, 10.6 °2θ, 14.6 °2θ, and 21.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

70. The compound of claim 1, wherein the solid form of DOM fumarate Form 1 is a crystalline polymorph of DOM fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2θ, 9.8 °2θ, and 25.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

71. The compound of claim 1 , wherein the solid form of DOM fumarate Form 1 is a crystalline polymorph of DOM fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2θ, 9.8 °2θ, 14.6 °2θ, 21.6 °2θ, and 25.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

72. The compound of claim 1, wherein the solid form of DOM fumarate Form 1 is a crystalline polymorph of DOM fumarate characterized by any combination of the XRPD peaks set forth in Table 6 (.±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

73. The compound of claim 1, wherein the solid form of DOM fumarate Form 1 is a crystalline polymorph of DOM fumarate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 4.

74. The compound of claim 1 , wherein the solid form of DOM fumarate Form 2 is a crystalline polymorph of DOM fumarate characterized by two or more, or three or more XR PD signals selected from the group consisting of 4.2 °2θ, 4.7 °2θ, and 10.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

75. The compound of claim 1, wherein the solid form of DOM fumarate Form 2 is a crystalline polymorph of DOM fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.2 °2θ, 4.7 °2θ, 10.3 °2θ, 12.7 °2θ, and 15.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

76. The compound of claim 1, wherein the solid form of DOM fumarate Form 2 is a crystalline polymorph of DOM fumarate characterized by two or more, or three or more XR PD signals selected from the group consisting of 4.7 °2θ, 12.7 °2θ, and 15.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

77. The compound of claim 1, wherein the solid form of DOM fumarate Form 2 is a crystalline polymorph of DOM fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.7 °2θ, 12.7 °2θ, 15.8 °2θ, 25.5 °2θ, and 4.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

78. The compound of claim 1 , wherein the solid form of DOM fumarate Form 2 is a crystalline polymorph of DOM fumarate characterized by any combination of the XRPD peaks set forth in Table 7 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

79. The compound of claim 1, wherein the solid form of DOM fumarate Form 2 is a crystalline polymorph of DOM fumarate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 63.

80. The compound of claim 1 , wherein the solid form of DOM gentisate is a. crystalline polymorph of DOM gentisate characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.2 °2θ, 13.9 °2θ, and 17.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

81. The compound of claim 1 , wherein the solid form of DOM gentisate is a. crystalline polymorph of DOM gentisate characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.2 °2θ, 13.9 °2θ, 15.5 °2θ, 17.6 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

82. The compound of claim 1, wherein the solid form of DOM gentisate is a crystalline polymorph of DOM gentisate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.6 °2θ, 26.5 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

83. The compound of claim 1, wherein the solid form of DOM gentisate is a crystalline polymorph of DOM gentisate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.6 °2θ, 26.5 °2θ, 22.0 °2θ, 23.5 °2θ, and 15.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

84. The compound of claim 1, wherein the solid form of DOM gentisate is a crystalline polymorph of DOM gentisate characterized by any combination of the XRPD peaks set forth in Table 8 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

85. The compound of claim 1, wherein the solid form of DOM gentisate is a crystalline poly morph of DOM gentisate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 5.

86. The compound of claim 1 , wherein the solid form of DOM glutamate is a crystalline polymorph of DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 9.9 °2θ, and 13.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

87. The compound of claim 1, wherein the solid form of DOM glutamate is a crystalline polymorph of DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 9.9 °2θ, 13.2 °2θ, 16.6 °2θ, and 17.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

88. The compound of claim 1, wherein the solid form of DOM glutamate is a crystalline polymorph of DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 26.6 °2θ, and 17.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation).

89. The compound of claim 1, wherein the solid form of DOM glutamate is a crystalline polymorph of DOM glutamate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.4 °2θ, 26.6 °2θ, 17.0 °2θ, 25.5 °2θ, and 13.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

90. The compound of claim 1, wherein the solid form of DOM glutamate is a crystalline polymorph of DOM glutamate characterized by any combination of the XRPD peaks set forth in Table 9 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

91. The compound of claim 1, wherein the solid form of DOM glutamate is a crystalline polymorph of DOM glutamate characterized by a XRl’D diffractogram substantially similar to that shown in FIG. 6.

92. The compound of claim 1, wherein the solid form of DOM glutamate is a crystalline polymorph of DOM glutamate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 30.

93. The compound of claim 1, wherein the solid form of DOM glutamate is a crystalline poly morph of DOM glutamate characterized by a TGA profile is substantially similar to that shown in FIG. 31.

94. The compound of claim 1 , wherein the solid form of DOM glutamate is a crystalline polymorph of DOM glutamate characterized by a DSC profile is substantially similar to that shown in FIG. 31.

95. The compound of claim 1, wherein the solid form of DOM glutarate Form 1 is a crystalline polymorph of DOM glutarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 5.9 °2θ, and 8.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

96. The compound of claim 1, wherein the solid form of DOM glutarate Form 1 is a crystalline polymorph of DOM glutarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 5.9 °2θ, 8.1 °2θ, 9.0 °2θ, and 12.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

97. The compound of claim 1, wherein the solid form of DOM glutarate Form 1 is a crystalline polymorph of DOM glutarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2θ, 21.8 °2θ, and 5.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

98. The compound of claim 1, wherein the solid form of DOM glutarate Form 1 is a crystalline polymorph of DOM glutarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2θ, 21.8 °2θ, 5.9 °2θ, 18.6 °2θ, and 8.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

99. The compound of claim 1, wherein the solid form of DOM glutarate Form 1 is a crystalline polymorph of DOM glutarate characterized by any combination of the XRPD peaks set forth in Table 10 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

100. The compound of claim 1, wherein the solid form of DOM glutarate Form 1 is a crystalline polymorph of DOM glutarate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 7.

101. The compound of claim 1, wherein the solid form of DOM glutarate Form 1 is a crystalline polymorph of DOM glutarate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 32.

102. The compound of claim 1 , wherein the solid form of DOM glutarate Form 1 is a. crystalline polymorph of DOM glutarate characterized by a TGA profile is substantially similar to that shown in FIG. 33.

103. The compound of claim 1, wherein the solid form of DOM glutarate Form 1 is a crystalline polymorph of DOM glutarate characterized by a DSC profile is substantially similar to that shown in FIG. 33.

104. The compound of claim 1 , wherein the solid form of DOM glutarate Form 2 is a. crystalline polymorph of DOM glutarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 8.5 °2θ, and 10.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

105. The compound of claim 1 , wherein the solid form of DOM glutarate Form 2 is a. crystalline polymorph of DOM glutarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 8.5 °2θ, 10.5 ^:29. 12.1 °2θ, and 19.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

106. The compound of claim 1, wherein the solid form of DOM glutarate Form 2 is a crystalline polymorph of DOM glutarate characterized by two or more, or three or more XRJ’D signals selected from the group consisting of 6.1 °2θ, 16.4 °2θ, and 19.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

107. The compound of claim 1, wherein the solid form of DOM glutarate Form 2 is a crystalline polymorph of DOM glutarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 16.4 °2θ, 19.8 °2θ, 15.6 °2θ, and 21.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

108. The compound of claim 1, wherein the solid form of DOM glutarate Form 2 is a crystalline polymorph of DOM glutarate characterized by any combination of the XRJ’D peaks set forth in Table 11 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

109. The compound of claim 1, wherein the solid form of DOM glutarate Form 2 is a crystalline polymorph of DOM glutarate characterized by a XRJ’D diffractogram substantially similar to that shown in FIG. 64.

1 10. The compound of claim 1 , wherein the solid form of DOM glutarate Form 2 is a. crystalline polymorph of DOM glutarate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 34.

111. The compound of claim 1, wherein the solid form of DOM glutarate Form 2 is a crystalline polymorph of DOM glutarate characterized by a TGA profile is substantially similar to that shown in FIG. 35.

112. The compound of claim 1 , wherein the solid form of DOM glutarate Form 2 is a. crystalline polymorph of DOM glutarate characterized by a DSC profile is substantially similar to that shown in FIG. 35.

113. The compound of claim 1, wherein the solid form of DOM hydrochloride is a. crystalline polymorph of DOM hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2θ, 13.3 °2θ, and 14.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

114. The compound of claim 1, wherein the solid form of DOM hydrochloride is a. crystalline polymorph of DOM hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2θ, 13.3 °2θ, 14.4 °2θ, 15.9 °2θ, and 16.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

115. The compound of claim 1, wherein the solid form of DOM hydrochloride is a crystalline polymorph of DOM hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2θ, 26.7 °2θ, and 15.9 °2θ (±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

116. The compound of claim 1, wherein the solid form of DOM hydrochloride is a crystalline polymorph of DOM hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2θ, 26.7 °2θ, 15.9 °2θ, 22.8 °2θ, and 25.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

117. The compound of claim 1, wherein the solid form of DOM hydrochloride is a crystalline polymorph of DOM hydrochloride characterized by any combination of the XRPD peaks set forth in Table 13 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

118. The compound of claim 1 , wherein the solid form of DOM hydrochloride is a crystalline polymorph of DOM hydrochloride characterized by a XRPD diffractogram substantially similar to that shown in FIG. 9.

119. The compound of claim 1, wherein the solid form of DOM hydrochloride is a. crystalline polymorph of DOM hydrochloride characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 38.

120. The compound of claim 1 , wherein the solid form of DOM hydrochloride is a crystalline polymorph of DOM hydrochloride characterized by a TGA profile is substantially similar to that shown in FIG. 39.

121. The compound of claim 1, wherein the solid form of DOM hydrochloride is a. crystalline polymorph of DOM hydrochloride characterized by a. DSC profile is substantially similar to that shown in FIG. 39.

122. The compound of claim 1, wherein the solid form of DOM l-hydroxy-2-naphthoate is a crystalline polymorph of DOM 1 -hydroxy-2-naphthoate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2θ, 10.0 °2θ, and 16.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

123. The compound of claim 1, wherein the solid form of DOM l-hydroxy-2-naphthoate is a crystalline polymorph of DOM I -hydroxy-2-naphthoate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2θ, 10.0 °2θ, 16.6 °2θ, 18.1 °2θ, and 24.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

124. The compound of claim 1, wherein the solid form of DOM l-hydroxy-2-naphthoate is a crystalline polymorph of DOM 1 -hydroxy-2-naphthoate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.0 °2θ, 16.6 °2θ, and 24.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

125. The compound of claim 1, wherein the solid form of DOM l-hydroxy-2-naphthoate is a crystalline polymorph of DOM 1 -hydroxy-2-naphthoate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.0 °2θ, 16.6 °2θ, 24.4 °2θ, 18.1 °2θ, and 21.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

126. The compound of claim 1 , wherein the solid form of DOM 1 -hydroxy-2-naphthoate is a crystalline polymorph of DOM 1 -hydroxy-2-naphthoate characterized by any combination of the XRPD peaks set forth in Table 14 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

127. The compound of claim 1, wherein the solid form of DOM 1 -hydroxy-2-naphthoate is a. crystalline polymorph of DOM 1 -hydroxy-2-naphthoate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 10.

128. The compound of claim 1 , wherein the solid form of DOM 1 -hydroxy-2-naphthoate is a crystalline polymorph of DOM 1 -hydroxy-2-naphthoate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 60.

129. The compound of claim 1, wherein the solid form of DOM 1 -hydroxy-2-naphthoate is a. crystalline polymorph of DOM l-hydroxy-2-naphthoate characterized by a TGA profile is substantially similar to that shown in FIG. 61.

130. The compound of claim 1, wherein the solid form of DOM l-hydroxy-2-naphthoate is a crystalline polymorph of DOM 1 -hydroxy-2-naphthoate characterized by a DSC profile is substantially similar to that shown in FIG. 61.

131. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.7 °2θ, 11.5 °2θ, and 14.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

132. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.7 °2θ, 11.5 °2θ, 14.0 °2θ, 16.4 °2θ, and 18.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

133. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.7 °2θ, 14.0 °2θ, and 22.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

134. The compound of claim 1 , wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.7 °2θ, 14.0 °2θ, 22.8 °2θ, 23.6 °2θ, and 19.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

135. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.7 °2θ, 14.0 °2θ, 22.8 °2θ, 23.6 °2θ, 19.9 °2θ, 25.1 °2θ, and 18.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

136. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.7 °2θ, 14.0 °2θ, 22.8 °2θ, 23.6 °2θ, 19.9 °2θ, 25.1 °2θ, 18.3 °2θ, 16.4 °2θ, 20.4 °2θ, and 22.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

137. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by any combination of the XRPD peaks set forth in Table 15 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

138. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 65.

139. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by a *¹H NMR spectrum substantially similar to that shown in FIG. 44.

140. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by a IGA profile is substantially similar to that shown in FIG. 45.

141. The compound of claim 1, wherein the solid form of DOM maleate Form 1 is a crystalline polymorph of DOM maleate characterized by a DSC profile is substantially similar to that shown in FIG. 45.

142. The compound of claim 1 , wherein the mixture of solid forms of DOM maleate Forms 1 and 2 is characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 11.5 °2θ, and 13.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

143. The compound of claim 1, wherein the mixture of solid forms of DOM maleate Forms 1 and 2 is characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 11.5 °2θ, 13.7 °2θ, 14.9 °2θ, and 16.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

144. The compound of claim 1, wherein the mixture of solid forms of DOM maleate Forms 1 and 2 is characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.8 °2θ, 23.6 °2θ, and 25.1 °2θ (.±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

145. The compound of claim 1 , wherein the mixture of solid forms of DOM maleate Forms 1 and 2 is characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.8 °2θ, 23.6 °2θ, 25.1 °2θ, 16.4 °2θ, and 22.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

146. The compound of claim 1 , wherein the mixture of solid forms of DOM maleate Forms 1 and 2 is characterized by any combination of the XRPD peaks set forth in Table 16 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

147. The compound of claim 1, wherein the mixture of solid forms of DOM maleate Forms I and 2 are characterized by a XRPD diffractogram substantially similar to that shown in FIG. 12.

148. The compound of claim 1, wherein the solid form of DOM maleate Form 2 is a crystalline polymorph of DOM maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7 °2θ, 13.7 °2θ, and 14.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

149. The compound of claim 1, wherein the solid form of DOM maleate Form 2 is a crystalline polymorph of DOM maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7 °2θ, 13.7 °2θ, 14.9 °2θ, 17.1 °2θ, and 17.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

150. The compound of claim 1 , wherein the solid form of DOM maleate Form 2 is a crystalline polymorph of DOM maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7 °2θ, 13.7 °2θ, 14.9 °2θ, 17. 1 °2θ, 17.8 °2θ, and 28.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

151. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 16.3 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

152. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 15.7 °2θ, 16.3 °2θ, 17.2 °2θ, and 21.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

153. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 25.5 °2θ, and 21.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

154. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 25.5 °2θ, 21.2 °2θ, 26.1 °2θ, and 22.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

155. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by any combination of the XRPD peaks set forth in Table 17 (±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

156. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6 °2θ, 15.6 °2θ, 16.3 °2θ, 17.2 °2θ, and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

157. The compound of claim 1 , wherein the solid form of DOM malonate Form 1 is a. crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.4 °2θ, 16.3 °2θ, and 4.2 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

158. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 22.4 °2θ, 16.3 °2θ, 4.2 °2θ, 26.1 °2θ, and 26.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

159. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by any combination of the XRPD peaks set forth in Table 18 (±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

160. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 13.

161. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 66.

162. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by a ‘FI NMR spectrum substantially similar to that shown in FIG. 46.

163. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by a TGA profile is substantially similar to that shown in FIG. 47.

164. The compound of claim 1, wherein the solid form of DOM malonate Form 1 is a crystalline polymorph of DOM malonate characterized by a DSC profile is substantially similar to that shown in FIG. 47.

165. The compound of claim 1, wherein the solid form of DOM malonate Form 2 is a crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 1 1.8 °2θ, and 13.4 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

166. The compound of claim 1 , wherein the solid form of DOM malonate Form 2 is a. crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 11.8 °2θ, 13.4 °2θ, 15.8 °2θ, and 16.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

167. The compound of claim 1 , wherein the solid form of DOM malonate Form 2 is a. crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 15.8 °2θ, and 18.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

168. The compound of claim 1 , wherein the solid form of DOM malonate Form 2 is a. crystalline polymorph of DOM malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 15.8 °2θ, 18.8 °2θ, 16.5 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

169. The compound of claim 1, wherein the solid form of DOM malonate Form 2 is a crystalline polymorph of DOM malonate characterized by any combination of the XRPD peaks set forth in Table 19 (±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

170. The compound of claim 1, wherein the solid form of DOM malonate Form 2 is a crystalline polymorph of DOM malonate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 67.

171. The compound of claim 1, wherein the solid form of DOM mesylate is a crystalline polymorph of DOM mesy late characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.9 °2θ, 16.3 °2θ, and 17.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

172. The compound of claim 1, wherein the solid form of DOM mesy late is a crystalline polymorph of DOM mesy late characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.9 °2θ, 14.9 °2θ, 16.3 °2θ, 17.0 °2θ, and 22.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

173. The compound of claim 1 , wherein the solid form of DOM mesylate is a. crystalline polymorph of DOM mesy late characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.0 °2θ, 16.3 °2θ, and 4.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

174. The compound of claim 1, wherein the solid form of DOM mesylate is a crystalline polymorph of DOM mesy late characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.0 °2θ, 16.3 °2θ, 4.1 °2θ, 3.9 °2θ, and 24.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

175. The compound of claim 1, wherein the solid form of DOM mesy late is a crystalline polymorph of DOM mesy late characterized by any combination of the XRPD peaks set forth in Table 20 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

176. The compound of claim 1, wherein the solid form of DOM mesylate is a crystalline polymorph of DOM mesylate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 14.

177. The compound of claim 1, wherein the solid form of DOM mucate is a crystalline polymorph of DOM mucate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 9.2 °2θ, and 13.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation).

178. The compound of claim 1, wherein the solid form of DOM mucate is a crystalline polymorph of DOM mucate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 9.2 °2θ, 13.2 °2θ, 13.8 °2θ, and 16.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

179. The compound of claim 1, wherein the solid form of DOM mucate is a crystalline polymorph of DOM mucate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2θ, 13.8 °2θ, 9.2 °2θ, 25.4 °2θ, and 16.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

180. The compound of claim 1 , wherein the solid form of DOM mucate is a. crystalline polymorph of DOM mucate characterized by any combination of the XRPD peaks set forth in Table 21 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

181. The compound of claim 1, wherein the solid form of DOM mucate is a crystalline poly morph of DOM mucate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 21.

182. The compound of claim 1 , wherein the solid form of DOM mucate is a. crystalline polymorph of DOM mucate characterized by a. ¹H NMR spectrum substantially similar to that shown in FIG. 48.

183. The compound of claim 1, wherein the solid form of DOM mucate is a crystalline polymorph of DOM mucate characterized by a TGA profile is substantially similar to that shown in FIG. 49.

184. The compound of claim 1, wherein the solid form of DOM mucate is a crystalline polymorph of DOM mucate characterized by a. DSC profile is substantially similar to that shown in FIG. 49.

185. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 8.1 °2θ, and 12.2 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

186. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 8.1 °2θ, 12.2 °2θ, 16.7 °2θ, and 22.0 °2θ (.±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

187. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 12.2 °2θ, and 24.5 °2θ (±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

188. The compound of claim 1 , wherein the solid form of DOM phosphate is a. crystalline polymorph of DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 12.2 °2θ, 24.5 °2θ, 16.7 °2θ, and 22.0 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

189. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by any combination of the XRPD peaks set forth in Table 22 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

190. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 16.7 °2θ, and 22.0 °2θ (±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

191. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2θ, 16.7 °2θ, 22.0 °2θ, 24.6 °2θ, and 12.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

192. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline poly morph of DOM phosphate characterized by any combination of the XRPD peaks set forth in Table 23 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

193. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 16.

194. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 68.

195. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 50.

196. The compound of claim 1 , wherein the solid form of DOM phosphate is a. crystalline polymorph of DOM phosphate characterized by a I'GA profile is substantially similar to that shown in FIG. 51.

197. The compound of claim 1, wherein the solid form of DOM phosphate is a crystalline polymorph of DOM phosphate characterized by a DSC profile is substantially similar to that sho wn in FIG. 51.

198. The compound of claim 1 , wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.2 °2θ, 13.8 °2θ, and 20.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

199. The compound of claim 1 , wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by two or more, or three or more XR PD signals selected from the group consisting of 11.2 °2θ, 13.8 °2θ, 17.3 °2θ, 20.4 °2θ, and 20.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

200. The compound of claim 1, wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.4 °2θ, 13.8 °2θ, and 20.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

201. The compound of claim 1, wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by two or more, or three or more XR PD signals selected from the group consisting of 20.4 °2θ, 13.8 °2θ, 20.8 °2θ, 24.4 °2θ, and 25.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

202. The compound of claim 1, wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by any combination of the XRPD peaks set forth in Table 24 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

203. The compound of claim 1, wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 13.6 °2θ, and 14.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

204. The compound of claim 1 , wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2θ, 10.4 °2θ, 13.6 °2θ, 14.7 °2θ, and 20.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

205. The compound of claim 1 , wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 20.4 °2θ, 24.4 °2θ, and 14.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

206. The compound of claim 1 , wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by two or more, or three or more XR PD signals selected from the group consisting of 20.4 °2θ, 24.4 °2θ, 14.7 °2θ, 5.1 °2θ, and 13.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

207. The compound of claim 1, wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by any combination of the XRPD peaks set forth in Table 25 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

208. The compound of claim 1, wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 17.

209. The compound of claim 1, wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 69.

210. The compound of claim 1, wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 54.

211. The compound of claim 1 , wherein the solid form of DOM sulfate is a crystalline polymorph of DOM sulfate characterized by a TGA profile is substantially similar to that shown in FIG. 55.

212. The compound of claim 1, wherein the solid form of DOM sulfate is a. crystalline polymorph of DOM sulfate characterized by a DSC profile is substantially similar to that shown in FIG. 55.

213. The compound of claim 1 , wherein the solid form of DOM succinate is a. crystalline polymorph of DOM succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.8 °2θ, 9.6 °2θ, and 10.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation).

214. The compound of claim 1 , wherein the solid form of DOM succinate is a. crystalline polymorph of DOM succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.8 °2θ, 9.6 °2θ, 10.6 °2θ, 14.4 °2θ, and 19.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ: Cu Kα1 radiation).

215. The compound of claim 1, wherein the solid form of DOM succinate is a crystalline polymorph of DOM succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2θ, 4.8 °2θ, and 14.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or .±0.0 °2θ; Cu Kα1 radiation).

216. The compound of claim 1, wherein the solid form of DOM succinate is a crystalline polymorph of DOM succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2θ, 4.8 °2θ, 14.4 °2θ, 19.2 °2θ, and 21.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

217. The compound of claim 1, wherein the solid form of DOM succinate is a crystalline polymorph of DOM succinate characterized by any combination of the XRPD peaks set forth in Table 26 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

218. The compound of claim 1 , wherein the solid form of DOM succinate is a crystalline polymorph of DOM succinate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 18.

219. The compound of claim 1 , wherein the solid form of DOM succinate is a. crystalline polymorph of DOM succinate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 52.

220. The compound of claim 1, wherein the solid form of DOM succinate is a crystalline polymorph of DOM succinate characterized by a TGA profile is substantially similar to that shown in FIG. 53.

221. The compound of claim 1 , wherein the solid form of DOM succinate is a. crystalline polymorph of DOM succinate characterized by a. DSC profile is substantially similar to that shown in FIG. 53.

222. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 10.6 °2θ, and 12.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

223. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2θ, 10.6 °2θ, 12.2 °2θ, 18.4 °2θ, and 20.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

224. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.2 °2θ, 18.4 °2θ, and 13.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

225. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.2 °2θ, 18.4 °2θ, 13.7 °2θ, 21.0 °2θ, and 13.5 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

226. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by any combination of the XRPD peaks set forth in Table 27 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation). zz /. The compound of claim 1 , wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 12.1 °2θ, and 18.2 °2θ (±0.2 °2θ; ±0. 1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

228. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 12.1 °2θ, 13.6 °2θ, 18.2 °2θ, and 21.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

229. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2θ, 18.2 °2θ, and 13.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

230. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2θ, 18.2 °2θ, 13.6 °2θ, 21.1 °2θ, and 20.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

231. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by any combination of the XRPD peaks set forth in Table 28 (±0.2 °2θ; .±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

232. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 19.

233. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by a XR PD diffractogram substantially similar to that shown in FIG. 70.

234. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by a ^!1H NMR spectrum substantially similar to that shown in FIG. 56.

235. The compound of claim 1 , wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by a I'GA profile is substantially similar to that shown in FIG. 57.

236. The compound of claim 1, wherein the solid form of DOM L-tartrate Form 1 is a crystalline polymorph of DOM L-tartrate characterized by a DSC profile is substantially similar to that shown in FIG. 57.

237. The compound of claim 1 , wherein the solid form of DOM tosylate Form 1 is a crystalline polymorph of DOM tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 7.7 °2θ, and 11.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

238. The compound of claim 1 , wherein the solid form of DOM tosylate Form 1 is a crystalline polymorph of DOM tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2θ, 7.7 °2θ, 8.4 °2θ. 10.3 °2θ, and 11.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

239. The compound of claim 1, wherein the solid form of DOM tosylate Form 1 is a crystalline polymorph of DOM tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.9 °2θ, 6.0 °2θ, 7.7 °2θ, 22,0 °2θ, and 8.4 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

240. The compound of claim 1, wherein the solid form of DOM tosylate Form 1 is a crystalline polymorph of DOM tosylate characterized by any combination of the XRPD peaks set forth in Table 29 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

241. The compound of claim 1, wherein the solid form of DOM tosylate Form 1 is a crystalline polymorph of DOM tosylate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 20.

242. The compound of claim 1, wherein the solid form of DOM tosylate Form 1 is a crystalline polymorph of DOM tosylate characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 58.

243. The compound of claim 1 , wherein the solid form of DOM tosylate Form 1 is a crystalline polymorph of DOM tosy late characterized by a TGA profile is substantially similar to that shown in FIG. 59.

244. The compound of claim 1, wherein the solid form of DOM tosylate Form 1 is a crystalline polymorph of DOM tosylate characterized by a DSC profile is substantially similar to that shown in FIG. 59.

245. The compound of claim 1 , wherein the solid form of DOM tosylate Form 2 is a crystalline polymorph of DOM tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.8 °2θ, 7.9 °2θ, and 11.7 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

246. The compound of claim 1 , wherein the solid form of DOM tosylate Form 2 is a crystalline polymorph of DOM tosy late characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.8 °2θ, 7.9 °2θ, 11.7 °2θ, 14.2 °2θ, and 22.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

247. The compound of claim 1, wherein the solid form of DOM tosylate Form 2 is a crystalline polymorph of DOM tosy late characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7 °2θ, 22,3 °2θ, and 5.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

248. The compound of claim 1, wherein the solid form of DOM tosylate Form 2 is a crystalline polymorph of DOM tosy late characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7 °2θ, 22.3 °2θ, 5.8 °2θ, 7.9 °2θ, and 19.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

249. The compound of claim 1, wherein the solid form of DOM tosylate Form 2 is a crystalline polymorph of DOM tosy late characterized by any combination of the XRPD peaks set forth in Table 30 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

250. The compound of claim 1, wherein the solid form of DOM tosylate Form 2 is a crystalline polymorph of DOM tosylate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 71.

251. The compound of claim 1 , wherein the solid form of DOM ethanesulfonate is a crystalline polymorph of DOM ethanesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2θ, 13.0 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

252. The compound of claim 1, wherein the solid form of DOM ethanesulfonate is a crystalline polymorph of DOM ethanesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2θ, 13.0 °2θ, 15.1 °2θ, 20.0 °2θ, and 22.8 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

253. The compound of claim 1, wherein the solid form of DOM ethanesulfonate is a crystalline polymorph of DOM ethanesulfonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2θ, 22.8 °2θ, and 15.1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

254. The compound of claim 1, wherein the solid form of DOM ethanesulfonate is a crystalline polymorph of DOM ethanesulfonate characterized by any combination of the XRPD peaks set forth in Table 31 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

255. The compound of claim 1 , wherein the solid form of DOM ethanesulfonate is a crystalline polymorph of DOM ethanesulfonate characterized by a XRPD diffractogram substantially similar to that shown in FIG. 22.

256. The compound of claim 1, wherein the solid form of DOM ethanesulfonate is a crystalline polymorph of DOM ethanesulfonate characterized by a ¹H NMR spectrum substantially similar to that sho wn in FIG. 28.

257. The compound of claim 1 , wherein the solid form of DOM ethanesulfonate is a crystalline polymorph of DOM ethanesulfonate characterized by a TGA profile is substantially similar to that shown in FIG. 29.

258. The compound of claim 1, wherein the solid form of DOM ethanesulfonate is a crystalline polymorph of DOM ethanesulfonate characterized by a DSC profile is substantially similar to that shown in FIG. 29.

259. The compound of claim 1 , wherein the solid form of DOM lactate is a crystalline polymorph of DOM lactate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.3 °2θ, 12.5 °2θ, and 13. 1 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

260. The compound of claim 1, wherein the solid form of DOM lactate is a crystalline polymorph of DOM lactate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.3 °2θ, 12.5 °2θ, 13.1 °2θ, 14.6 °2θ, and 16.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

261. The compound of claim 1, wherein the solid form of DOM lactate is a cry stalline polymorph of DOM lactate characterized by two or more, or three or more XRPD signals selected from the group consisting of 25.3 °2θ, 21.6 °2θ, and 16.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

262. The compound of claim 1, wherein the solid form of DOM lactate is a cry stalline polymorph of DOM lactate characterized by two or more, or three or more XRPD signals selected from the group consisting of 25.3 °2θ, 21.6 °2θ, 16.2 °2θ, 13.1 °2θ, and 14.6 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

263. The compound of claim 1, wherein the solid form of DOM lactate is a crystalline polymorph of DOM lactate characterized by any combination of the XRPD peaks set forth in Table 32 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

264. The compound of claim 1, wherein the solid form of DOM lactate is a crystalline poly morph of DOM lactate characterized by a XRPD diffractogram substantially similar to that sho wn in FIG. 23.

265. The compound of claim 1, wherein the solid form of DOM lactate is a crystalline polymorph of DOM lactate characterized by a ^!1H NMR spectrum substantially similar to that shown in FIG. 40.

266. The compound of claim 1, wherein the solid form of DOM lactate is a crystalline polymorph of DOM lactate characterized by a TGA profile is substantially similar to that shown in FIG. 41.

267. The compound of claim 1 , wherein the solid form of DOM lactate is a crystalline polymorph of DOM lactate characterized by a DSC profile is substantially similar to that shown in FIG. 41.

268. The compound of claim 1, wherein the solid form of DOM Form A is a. crystalline polymorph of DOM characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.0 °2θ, 12.5 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

269. The compound of claim 1, wherein the solid form of DOM Form A is a. crystalline polymorph of DOM characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.8 °2θ, 11.5 °2θ, 12.0 °2θ, 12.5 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

270. The compound of claim 1, wherein the solid form of DOM Form A is a crystalline polymorph of DOM characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.5 °2θ, 12.0 °2θ, and 17.2 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

271. The compound of claim 1, wherein the solid form of DOM Form A is a crystalline polymorph of DOM characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.5 °2θ, 12.0 °2θ, 17.2 °2θ, 17.4 °2θ, and 24.9 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

272. The compound of claim 1, wherein the solid form of DOM Form A is a crystalline polymorph of DOM characterized by any combination of the XRPD peaks set forth in Table 36 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

273. The compound of claim 1, wherein the solid form of DOM Form A is a crystalline polymorph of DOM characterized by a XRPD diffractogram substantially similar to that shown in FIG. 72.

274. The compound of claim 1, wherein the solid form of DOM Form A is a crystalline polymorph of DOM characterized by a ¹H NMR spectrum substantially similar to that shown in FIG. 74.

275. The compound of claim 1 , wherein the solid form of DOM Form A is a crystalline polymorph of DOM characterized by a TGA profile is substantially similar to that sho wn in FIG. 75.

276. The compound of claim 1, wherein the solid form of DOM Form A is a. crystalline polymorph of DOM characterized by a DSC profile is substantially similar to that shown in FIG. 75.

277. The compound of claim 1 , wherein the solid form of DOM Form A is a crystalline polymorph of DOM characterized by an FT-IR spectrum is substantially similar to that shown in FIG. 76.

278. The solid form of claim 1 , wherein the solid form is a solid form of DOI.

279. The compound of claim 1 , wherein the solid form of DOI is a salt of DOI.

280. The compound of claim 1, wherein the salt of DOI is a crystalline salt.

281. The compound of claim 1 , wherein the solid form of DOI HCl is a crystalline polymorph of DOI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.8 °2θ, 8.2 °2θ, and 10.2 °2θ (±0.2 °2θ; ±0.1 °2θ, or ±0.0 °2θ; Cu Kα1 radiation).

282. The compound of claim 1 , wherein the solid form of DOI HCl is a crystalline polymorph of DOI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.8 °2θ, 8.2 °2θ, 10.2 °2θ, 19.4 °2θ, and 23.5 °2θ (±0.2 °2θ. ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

283. The compound of claim 1 , wherein the solid form of DOI HCl is a crystalline polymorph of DOI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 23.5 °2θ, 7.8 °2θ, and 16.5 °2θ (±0.2 °2θ, ±0.1 °2θ, or ±0.0 °2θ; Cu Kα1 radiation).

284. The compound of claim 1 , wherein the solid form of DOI HCl is a crystalline polymorph of DOI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 23.5 °2θ, 7.8 °2θ, 16.5 °2θ, 22.7 °2θ, and 16.3 °2θ (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

285. The compound of claim 1 , wherein the solid form of DOI HCl is a crystalline polymorph of DOI HCl characterized by any combination of the XRPD peaks set forth in Table 37 (±0.2 °2θ; ±0.1 °2θ; or ±0.0 °2θ; Cu Kα1 radiation).

286. The compound of claim 1, wherein the solid form of DOI HCl is a crystalline polymorph of DOI HCl characterized by a XRPD diffractogram substantially similar to that shown in FIG. 79.

287. The solid form of claim 1, wherein the solid form is a solid form of DOB.

288. The compound of claim 1, wherein the solid form of DOB is a. salt of DOB.

289. The compound of claim 1 , wherein the salt of DOB is a. crystalline salt.

290. The solid form of claim 1 , wherein the solid form is a solid form of DOC.

291. The compound of claim 1 , wherein the solid form of DOC is a salt of DOC.

292. The compound of claim 1, wherein the salt of DOC is a crystalline salt.

293. A pharmaceutical composition, comprising a solid form of a compound according to of any one of the preceding claims, and a pharmaceuti cally acceptable excipient.

294. A method, comprising administering to a subject an effective amount of a solid, form of any one of the preceding claims, or a. pharmaceutical composition thereof.

295. The method of claim 294, wherein the subject has a neurological disorder or a psychiatric disorder, or both.

296. The method of claim 294, wherein subject has a neurological disorder which is a neurodegenerative disorder.

297. The method, of claim 295, wherein the neurological disorder or psychiatric disorder, or both, comprises depression, addiction, anxiety, or a post-traumatic stress disorder.

298. The method, of claim 295, wherein the neurological disorder or psychiatric disorder, or both, comprises treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, or substance use disorder.

299. The method of claim 295, wherein the neurological disorder or psychiatric disorder, or both, comprises stroke, traumatic brain injury, or a combination thereof. 300. The method of any of the preceding claims, wherein administering comprises oral, parenteral, or topical administration. 301. The method of any of the preceding claims, wherein administering comprises oral administration. 302. The method of any of the preceding claims, wherein administering comprises administering by injection, inhalation, intraocular, intravaginal, intrarectal or transdermal routes. 303. The method of any of the preceding claims, further comprising administering to the subject an effective amount of an empathogenic agent. 304. The method of any of the preceding claims, further comprising administering a 5-HT_2A antagonist to the subject. 305. The method of claim 304, wherein the 5-HT_2A antagonist is selected from MDL-11,939, eplivanserin (SR-46,349), ketanserin, ritanserin, altanserin, acepromazine, mianserin, mirtazapine, quetiapine, SB204741, SB206553, SB242084, LY272015, SB243213, blonanserin, SB200646, RS102221, nefazodone, MDL-100,907, pimavanserin, pruvanserin, nelotanserin and lorcaserin. 306. Use of a compound or composition of any of the preceding claims, in a method of treating a subject with a neurological disorder or a psychiatric disorder, or both. 307. Use of a compound or composition of any of the preceding claims, in a method of treating a subject with a neurological disorder which is a neurodegenerative disorder. 308. The use of claim 306, wherein the neurological disorder or psychiatric disorder, or both, comprises depression, addiction, anxiety, or a post-traumatic stress disorder. 309. The use of claim 306, wherein the neurological disorder or psychiatric disorder, or both, comprises treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, or substance use disorder.

310. The use of claim 306, wherein the neurological disorder or psychiatric disorder, or both, comprises stroke, traumatic brain injury, or a combination thereof. 311. The use of any of the preceding claims, wherein administering comprises oral, parenteral, or topical administration. 312. The use of any of the preceding claims, wherein administering comprises oral administration. 313. The use of any of the preceding claims, wherein administering comprises administering by injection, inhalation, intraocular, intravaginal, intrarectal or transdermal routes. 314. The use of any of the preceding claims, further comprising administering to the subject an effective amount of an empathogenic agent. 315. The use of any of the preceding claims, further comprising administering a 5-HT_2A antagonist to the subject. 316. The use of claim 315, wherein the 5-HT_2A antagonist is selected from MDL-11,939, eplivanserin (SR-46,349), ketanserin, ritanserin, altanserin, acepromazine, mianserin, mirtazapine, quetiapine, SB204741, SB206553, SB242084, LY272015, SB243213, blonanserin, SB200646, RS102221, nefazodone, MDL-100,907, pimavanserin, pruvanserin, nelotanserin and lorcaserin. 317. Use of a compound or composition of any of the preceding claims, in the manufacture of a medicament for treating a subject with a neurological disorder or a psychiatric disorder, or both. 318. Use of a compound or composition of any of the preceding claims, in the manufacture of a medicament for treating a subject with a neurological disorder which is a neurodegenerative disorder. 319. The use of claim 317, wherein the neurological disorder or psychiatric disorder, or both, comprises depression, addiction, anxiety, or a post-traumatic stress disorder.

320. The use of claim 317, wherein the neurological disorder or psychiatric disorder, or both, comprises treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, or substance use disorder. 321. The use of claim 317, wherein the neurological disorder or psychiatric disorder, or both, comprises stroke, traumatic brain injury, or a combination thereof. 322. The use of any of the preceding claims, wherein administering comprises oral, parenteral, or topical administration. 323. The use of any of the preceding claims, wherein administering comprises oral administration. 324. The use of any of the preceding claims, wherein administering comprises administering by injection, inhalation, intraocular, intravaginal, intrarectal or transdermal routes. 325. The use of any of the preceding claims, further comprising administering to the subject an effective amount of an empathogenic agent. 326. The use of any of the preceding claims, further comprising administering a 5-HT_2A antagonist to the subject. 327. The use of claim 326, wherein the 5-HT_2A antagonist is selected from MDL-11,939, eplivanserin (SR-46,349), ketanserin, ritanserin, altanserin, acepromazine, mianserin, mirtazapine, quetiapine, SB204741, SB206553, SB242084, LY272015, SB243213, blonanserin, SB200646, RS102221, nefazodone, MDL-100,907, pimavanserin, pruvanserin, nelotanserin and lorcaserin.