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WO2024118767A2 - Tryptamine derivatives - Google Patents

Tryptamine derivatives Download PDF

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Publication number
WO2024118767A2
WO2024118767A2 PCT/US2023/081591 US2023081591W WO2024118767A2 WO 2024118767 A2 WO2024118767 A2 WO 2024118767A2 US 2023081591 W US2023081591 W US 2023081591W WO 2024118767 A2 WO2024118767 A2 WO 2024118767A2
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WO
WIPO (PCT)
Prior art keywords
crystalline
purified
crystalline form
fumarate
meo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/US2023/081591
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French (fr)
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WO2024118767A3 (en
Inventor
Andrew R. Chadeayne
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Caamtech Inc
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Caamtech Inc
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Publication date
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Publication of WO2024118767A2 publication Critical patent/WO2024118767A2/en
Publication of WO2024118767A3 publication Critical patent/WO2024118767A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16—Tryptamines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/15—Fumaric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • Provisional Application No. 63/385,667 filed on December 1, 2022; U.S. Provisional Application No. 63/386,501, filed on December 8, 2022; U.S. Provisional Application No. 63/386,523, filed on December 8, 2022; U.S. Provisional Application No. 63/386,534, filed on December 8, 2022; U.S. Provisional Application No. 63/386,502, filed on December 8, 2022; and U.S. Provisional Application No. 63/386,503, filed on December 8, 2022; the disclosures of which are each incorporated herein by reference.
  • This disclosure relates to bis(2 ⁇ (5 ⁇ methoxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium) (2E) ⁇ but ⁇ 2 ⁇ enedioate (5 ⁇ methoxytryptammonium fumarate or 5 ⁇ MeO ⁇ T fumarate), crystalline 5 ⁇ MeO ⁇ T fumarate, and specific crystalline forms thereof, including crystalline form 1 of 5 ⁇ MeO ⁇ T fumarate; to pharmaceutical compositions containing 5 ⁇ MeO ⁇ T fumarate or crystalline 5 ⁇ MeO ⁇ T fumarate, including crystalline form 1 of 5 ⁇ MeO ⁇ T fumarate; and to methods of treatment/therapeutic uses of 5 ⁇ MeO ⁇ T fumarate or crystalline 5 ⁇ MeO ⁇ T fumarate, including crystalline form 1 of 5 ⁇ MeO ⁇ T fumarate.
  • This disclosure further relates to 2 ⁇ (1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 3 ⁇ carboxy ⁇ 2 ⁇ hydroxypropanoate (tryptammonium hydromalate), crystalline tryptammonium hydromalate, and specific crystalline forms thereof, including crystalline form 1 of tryptammonium hydromalate; to pharmaceutical compositions containing tryptammonium hydromalate or crystalline tryptammonium hydromalate, including crystalline form 1 of tryptammonium hydromalate; and to methods of treatment/therapeutic uses of tryptammonium hydromalate or crystalline tryptammonium hydromalate, including crystalline form 1 of tryptammonium hydromalate.
  • This disclosure further relates to 2 ⁇ (1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 2 ⁇ carboxybenzoate (tryptammonium hydrophthalate), crystalline tryptammonium hydrophthalate, and specific crystalline forms thereof, including crystalline form 1 of tryptammonium hydrophthalate; to pharmaceutical compositions containing tryptammonium hydrophthalate or crystalline tryptammonium hydrophthalate, including crystalline form 1 of tryptammonium hydrophthalate; and to methods of treatment/therapeutic uses of tryptammonium hydrophthalate or crystalline tryptammonium hydrophthalate, including crystalline form 1 of tryptammonium hydrophthalate.
  • This disclosure further relates to bis([2 ⁇ (4 ⁇ methoxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl](methyl)(propan ⁇ 2 ⁇ yl)azanium) (2E) ⁇ but ⁇ 2 ⁇ enedioate (4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate or 4 ⁇ MeO ⁇ MiPT fumarate), crystalline 4 ⁇ MeO ⁇ MiPT fumarate, and specific crystalline forms thereof, including crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fumarate; to pharmaceutical compositions containing 4 ⁇ MeO ⁇ MiPT fumarate or crystalline 4 ⁇ MeO ⁇ MiPT fumarate, including crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fumarate; and to methods of treatment/therapeutic uses of 4 ⁇ MeO ⁇ MiPT fumarate or crystalline 4 ⁇ MeO ⁇ MiPT fumarate, including crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fuma
  • This disclosure further relates to 2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 2 ⁇ [2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl]azaniumyl ⁇ butanedioate (5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium or 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T), crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, and specific crystalline forms thereof, including crystalline form 1 of 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T; to pharmaceutical compositions containing 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T or crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, including crystalline form 1 of 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇
  • This disclosure further relates to 2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 3 ⁇ carboxy ⁇ 2 ⁇ hydroxypropanoate (5 ⁇ chlorotryptammonium hydromaleate or 5 ⁇ Cl ⁇ T hydromaleate), crystalline 5 ⁇ Cl ⁇ T hydromaleate, and specific crystalline forms thereof, including crystalline form 1 of 5 ⁇ Cl ⁇ T hydromaleate; to pharmaceutical compositions containing 5 ⁇ Cl ⁇ T hydromaleate or crystalline 5 ⁇ Cl ⁇ T hydromaleate, including crystalline form 1 of 5 ⁇ Cl ⁇ T hydromaleate; and to methods of treatment/therapeutic uses of 5 ⁇ Cl ⁇ T hydromaleate or crystalline 5 ⁇ Cl ⁇ T hydromaleate, including crystalline form 1 of 5 ⁇ Cl ⁇ T hydromaleate.
  • This disclosure further relates to bis(2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium) 2 ⁇ hydroxybutanedioate (5 ⁇ chlorotryptammonium malate or 5 ⁇ Cl ⁇ T malate), crystalline 5 ⁇ Cl ⁇ T malate, and specific crystalline forms thereof, including crystalline form 1 of 5 ⁇ Cl ⁇ T malate; to pharmaceutical compositions containing 5 ⁇ Cl ⁇ T malate or crystalline 5 ⁇ Cl ⁇ T malate, including crystalline form 1 of 5 ⁇ Cl ⁇ T malate; and to methods of treatment/therapeutic uses of 5 ⁇ Cl ⁇ T malate or crystalline 5 ⁇ Cl ⁇ T malate, including crystalline form 1 of 5 ⁇ Cl ⁇ T malate.
  • This disclosure further relates to 2 ⁇ (5 ⁇ methyl ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ amine (5 ⁇ methyltryptamine or 5 ⁇ Me ⁇ T), crystalline 5 ⁇ Me ⁇ T, and specific crystalline forms thereof, including crystalline form 1 of 5 ⁇ Me ⁇ T; to pharmaceutical compositions containing 5 ⁇ Me ⁇ T or crystalline 5 ⁇ Me ⁇ T, including crystalline form 1 of 5 ⁇ Me ⁇ T; and to methods of treatment/therapeutic uses of 5 ⁇ Me ⁇ T or crystalline 5 ⁇ Me ⁇ T, including crystalline form 1 of 5 ⁇ Me ⁇ T.
  • This disclosure further relates to [2 ⁇ (4 ⁇ hydroxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl]bis(propan ⁇ 2 ⁇ yl)azanium (2E) ⁇ 3 ⁇ carboxyprop ⁇ 2 ⁇ enoate (4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate or 4 ⁇ HO ⁇ DiPT hydrofumarate), crystalline 4 ⁇ HO ⁇ DiPT hydrofumarate, and specific crystalline forms thereof, including crystalline form 1 of 4 ⁇ HO ⁇ DiPT hydrofumarate; to pharmaceutical compositions containing 4 ⁇ HO ⁇ DiPT hydrofumarate or crystalline 4 ⁇ HO ⁇ DiPT hydrofumarate, including crystalline form 1 of 4 ⁇ HO ⁇ DiPT hydrofumarate; and to methods of treatment/therapeutic uses of 4 ⁇ HO ⁇ DiPT hydrofumarate or crystalline 4 ⁇ HO ⁇ DiPT hydrofumarate, including crystalline form 1 of 4 ⁇ HO ⁇ DiPT hydrofumarate
  • API molecular weight is used to calculate the concentration of compositions comprising that API.
  • inaccuracies in molecular weight may lead to errors in the calculations pertaining to dosing, potency, toxicity, etc. in all downstream in vitro and in vivo assays that correlated the concentration of the API with a measured property. Accordingly, there remains a need to obtain and characterize crystalline forms of APIs, such as tryptamines and other psychedelic drug compounds.
  • XRPD X ⁇ ray powder diffraction
  • This disclosure further relates to 2 ⁇ (1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 3 ⁇ carboxy ⁇ 2 ⁇ hydroxypropanoate (tryptammonium hydromalate), crystalline tryptammonium hydromalate, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of tryptammonium hydromalate, including crystalline form 1 of tryptammonium hydromalate.
  • XRPD X ⁇ ray powder diffraction
  • XRPD X ⁇ ray powder diffraction
  • This disclosure further relates to bis([2 ⁇ (4 ⁇ methoxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl](methyl)(propan ⁇ 2 ⁇ yl)azanium) (2E) ⁇ but ⁇ 2 ⁇ enedioate (4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate or 4 ⁇ MeO ⁇ MiPT fumarate), crystalline 4 ⁇ MeO ⁇ MiPT fumarate, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of 4 ⁇ MeO ⁇ MiPT fumarate, including crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fumarate.
  • XRPD X ⁇ ray powder diffraction
  • This disclosure further relates to [2 ⁇ (4 ⁇ hydroxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl](propan ⁇ 2 ⁇ yl)propylazanium (2E) ⁇ 3 ⁇ carboxyprop ⁇ 2 ⁇ enoate (4 ⁇ hydroxy ⁇ N ⁇ propyl ⁇ N ⁇ isopropyltryptammnonium hydrofumarate or 4 ⁇ HO ⁇ PiPT hydrofumarate), crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of 4 ⁇ HO ⁇ PiPT hydrofumarate, including crystalline form 1 of 4 ⁇ HO ⁇ PiPT hydrofumarate.
  • XRPD X ⁇ ray powder diffraction
  • This disclosure further relates to 2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 2 ⁇ [2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl]azaniumyl ⁇ butanedioate (5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium or 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T), crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, including crystalline form 1 of 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T.
  • XRPD X ⁇ ray powder diffraction
  • XRPD X ⁇ ray powder diffraction
  • This disclosure further relates to 2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 2 ⁇ carboxybenzoate (5 ⁇ chlorotryptammonium hydrophthalate or 5 ⁇ Cl ⁇ T hydrophthalate), crystalline 5 ⁇ Cl ⁇ T hydrophthalate, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of 5 ⁇ Cl ⁇ T hydrophthalate, including crystalline form 1 of 5 ⁇ Cl ⁇ T hydrophthalate.
  • XRPD X ⁇ ray powder diffraction
  • This disclosure further relates to bis(2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium) 2 ⁇ hydroxybutanedioate (5 ⁇ chlorotryptammonium malate or 5 ⁇ Cl ⁇ T malate), crystalline 5 ⁇ Cl ⁇ T malate, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of 5 ⁇ Cl ⁇ T malate, including crystalline form 1 of 5 ⁇ Cl ⁇ T malate.
  • This disclosure further relates to 2 ⁇ (5 ⁇ methoxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 2 ⁇ [2 ⁇ (5 ⁇ methoxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl]azaniumyl ⁇ butanedioate (5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium or 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T), crystalline 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T, and specific crystalline forms thereof.
  • XRPD X ⁇ ray powder diffraction
  • This disclosure further relates to 2 ⁇ (5 ⁇ methyl ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ amine (5 ⁇ methyltryptamine or 5 ⁇ Me ⁇ T), crystalline 5 ⁇ Me ⁇ T, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of 5 ⁇ Me ⁇ T, including crystalline form 1 of 5 ⁇ Me ⁇ T.
  • XRPD X ⁇ ray powder diffraction
  • This disclosure further relates to bis(N ⁇ [2 ⁇ (4 ⁇ hydroxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl] ⁇ N ⁇ methylcyclopropanaminium) (2E) ⁇ but ⁇ 2 ⁇ enedioate (4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropyltryptammonium fumarate or 4 ⁇ HO ⁇ MCPT fumarate), crystalline 4 ⁇ HO ⁇ MCPT fumarate, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of 4 ⁇ HO ⁇ MCPT fumarate, including crystalline form 1 of 4 ⁇ HO ⁇ MCPT fumarate.
  • This disclosure further relates to [2 ⁇ (4 ⁇ hydroxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl]bis(propan ⁇ 2 ⁇ yl)azanium (2E) ⁇ 3 ⁇ carboxyprop ⁇ 2 ⁇ enoate (4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate or 4 ⁇ HO ⁇ DiPT hydrofumarate), crystalline 4 ⁇ HO ⁇ DiPT hydrofumarate, and specific crystalline forms thereof.
  • this disclosure pertains to particular crystalline forms of 4 ⁇ HO ⁇ DiPT hydrofumarate, including crystalline form 1 of 4 ⁇ HO ⁇ DiPT hydrofumarate.
  • XRPD X ⁇ ray powder diffraction
  • the disclosure further relates to a composition comprising 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, or specific crystalline forms thereof, such as crystalline form 1 of 5 ⁇ MeO ⁇ T fumarate, and at least one excipient.
  • the disclosure further relates to a composition comprising tryptammonium hydromalate, crystalline tryptammonium hydromalate, or specific crystalline forms thereof, such as crystalline form 1 of tryptammonium hydromalate, and at least one excipient.
  • the disclosure further relates to a composition comprising tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, or specific crystalline forms thereof, such as crystalline form 1 of tryptammonium hydrophthalate, and at least one excipient.
  • the disclosure further relates to a composition comprising 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, or specific crystalline forms thereof, such as crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fumarate, and at least one excipient.
  • the disclosure further relates to a composition comprising 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, or specific crystalline forms thereof, such as crystalline form 1 of 4 ⁇ HO ⁇ PiPT hydrofumarate, and at least one excipient.
  • the disclosure further relates to a composition comprising 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, or specific crystalline forms thereof, such as crystalline form 1 of 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, and at least one excipient.
  • the disclosure further relates to a composition comprising 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, or specific crystalline forms thereof, such as crystalline form 1 of 5 ⁇ Cl ⁇ T hydromaleate, and at least one excipient.
  • the disclosure further relates to a composition comprising 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, or specific crystalline forms thereof, such as crystalline form 1 of 5 ⁇ Cl ⁇ T hydrophthalate, and at least one excipient.
  • the disclosure further relates to a composition comprising 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, or specific crystalline forms thereof, such as crystalline form 1 of 5 ⁇ Cl ⁇ T malate, and at least one excipient.
  • the disclosure further relates to a composition comprising 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T, crystalline 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T, or specific crystalline forms thereof, such as crystalline form 1 of 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T, and at least one excipient.
  • the disclosure further relates to a composition
  • a composition comprising 4 ⁇ HO ⁇ DiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ DiPT hydrofumarate, or specific crystalline forms thereof, such as crystalline form 1 of 4 ⁇ HO ⁇ DiPT hydrofumarate, and at least one excipient.
  • the disclosure also provides a composition comprising 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc
  • the disclosure also relates to a method of preventing or treating a psychological disorder comprising the step of administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T
  • the disclosure further relates to a method of preventing or treating inflammation and/or pain, preventing or treating a neurological disorder, modulating activity of a mitogen ⁇ activated protein kinase (MAPK), modulating neurogenesis, or modulating neurite outgrowth comprising the step of administering to a subject in need thereof a therapeutically effective amount of a compound of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T
  • a subject in need thereof refers to a person requiring a composition to treat a particular disease or condition (e.g., inflammation, pain, a psychological disorder, modulating activity at a receptor, etc.).
  • the “subject in need thereof” may be identified by analyzing, diagnosing, and/or determining whether the person (or subject) requires the composition for treatment of a particular disease or condition.
  • identifying a person in need of treatment comprises diagnosing a person with a medical condition, e.g., a neurological disorder, a chemical imbalance, a hereditary condition, etc.
  • identifying a person in need of treatment comprises performing a psychiatric evaluation.
  • identifying a person in need of treatment comprises performing a blood test. In one embodiment, identifying a person in need of treatment comprises determining whether a person has a compulsive disorder. In one embodiment, identifying a person in need of treatment comprises self ⁇ identifying as having a compulsive disorder.
  • FIG. 1 shows the molecular structure of crystalline form 1 of 5 ⁇ methoxytryptammonium fumarate.
  • FIG. 2 shows the molecular structure of crystalline form 1 of tryptammonium hydromalate.
  • FIG. 3 shows the molecular structure of crystalline form 1 of tryptammonium hydrophthalate. [049] FIG.
  • FIG. 4 shows the molecular structure of crystalline form 1 of 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate.
  • FIG. 5 shows the molecular structure of crystalline form 1 of 4 ⁇ hydroxy ⁇ N ⁇ propyl ⁇ N ⁇ isopropyltryptammnonium hydrofumarate.
  • FIG. 6 shows the molecular structure of crystalline form 1 of 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium.
  • FIG. 7 shows the molecular structure of crystalline form 1 of 5 ⁇ chlorotryptammonium hydromaleate. [053] FIG.
  • FIG. 8 shows the molecular structure of crystalline form 1 of 5 ⁇ chlorotryptammonium hydrophthalate.
  • FIG. 9 shows the molecular structure of crystalline form 1 of 5 ⁇ chlorotryptammonium malate.
  • FIG. 10 shows the molecular structure of crystalline form 1 of 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium.
  • FIG. 11 shows the molecular structure of crystalline form 1 of 5 ⁇ methyltryptamine.
  • FIG. 12 shows the molecular structure of crystalline form 1 of 4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropyltryptammonium fumarate. [058] FIG.
  • FIG. 13 shows the molecular structure of crystalline form 1 of 4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate.
  • FIG. 14 shows the unit cell of crystalline form 1 of 5 ⁇ methoxytryptammonium fumarate along the a ⁇ axis.
  • FIG. 15 shows the unit cell of crystalline form 1 of tryptammonium hydromalate along the a ⁇ axis.
  • FIG. 16 shows the unit cell of crystalline form 1 of tryptammonium hydrophthalate along the b ⁇ axis.
  • FIG. 17 shows the unit cell of crystalline form 1 of 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate along the c ⁇ axis.
  • FIG. 18 shows the unit cell of crystalline form 1 of 4 ⁇ hydroxy ⁇ N ⁇ propyl ⁇ N ⁇ isopropyltryptammnonium hydrofumarate along the a ⁇ axis.
  • FIG. 19 shows the unit cell of crystalline form 1 of 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium along the a ⁇ axis. [065] FIG.
  • FIG. 20 shows the unit cell of crystalline form 1 of 5 ⁇ chlorotryptammonium hydromaleate along the b ⁇ axis.
  • FIG. 21 shows the unit cell of crystalline form 1 of 5 ⁇ chlorotryptammonium hydrophthalate along the c ⁇ axis.
  • FIG. 22 shows the unit cell of crystalline form 1 of 5 ⁇ chlorotryptammonium malate along the a ⁇ axis.
  • FIG. 23 shows the unit cell of crystalline form 1 of 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium along the a ⁇ axis. [069] FIG.
  • FIG. 24 shows the unit cell of crystalline form 1 of 5 ⁇ methyltryptamine along the a ⁇ axis.
  • FIG. 25 shows the unit cell of crystalline form 1 of 4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropyltryptammonium fumarate along the b ⁇ axis.
  • FIG. 26 shows the unit cell of crystalline form 1 of 4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate along the a ⁇ axis.
  • FIG. 27 shows the 2:1 ratio of crystalline form 1 of 5 ⁇ methoxytryptammonium fumarate as a dimer. [073] FIG.
  • FIG. 28 shows the 2:1 ratio of crystalline form 1 of 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate as a dimer.
  • FIG. 29 shows the 2:1 ratio of crystalline form 1 of 4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropyltryptammonium fumarate as a dimer.
  • FIG. 30 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ methoxytryptammonium fumarate.
  • FIG. 31 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of tryptammonium hydromalate.
  • FIG. 32 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of tryptammonium hydrophthalate.
  • FIG. 33 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate.
  • FIG. 34 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 4 ⁇ hydroxy ⁇ N ⁇ propyl ⁇ N ⁇ isopropyltryptammnonium hydrofumarate.
  • FIG. 35 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium.
  • FIG. 36 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ chlorotryptammonium hydromaleate.
  • FIG. 37 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ chlorotryptammonium hydrophthalate.
  • FIG. 35 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium.
  • FIG. 36 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ chlorotryptammonium hydromaleate
  • FIG. 38 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ chlorotryptammonium malate.
  • FIG. 39 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium.
  • FIG. 40 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ methyltryptamine.
  • FIG. 41 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropypltrytammonium fumarate.
  • FIG. 42 shows the simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate.
  • 5 ⁇ MeO ⁇ T fumarate has the following chemical formula: [091] Tryptammonium hydromalate has the following chemical formula: [092] Tryptammonium hydrophthalate has the following chemical formula: [093] 4 ⁇ MeO ⁇ MiPT fumarate has the following chemical formula: [094] 4 ⁇ HO ⁇ PiPT hydrofumarate has the following chemical formula: [095] 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T has the following chemical formula: [096] 5 ⁇ Cl ⁇ T hydromaleate has the following chemical formula: [097] 5 ⁇ Cl ⁇ T hydrophthalate has the following chemical formula: [098] 5 ⁇ Cl ⁇ T malate has the following chemical formula: [099] 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T has the following chemical formula: [100] 5 ⁇ Me ⁇ T has the following chemical formula: [101] 4 ⁇ HO ⁇ MCPT fumarate has the following chemical formula: [102] 4
  • Methods of the disclosure also relate to the administration of a therapeutically effective amount of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO ⁇ T
  • the disclosure provides a method for preventing and/or treating a psychological disorder by administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline
  • the psychological disorder may be chosen from: depression; psychotic disorder; schizophrenia; schizophreniform disorder (acute schizophrenic episode); schizoaffective disorder; bipolar I disorder (mania, manic disorder, manic ⁇ depressive psychosis); bipolar II disorder; major depressive disorder; major depressive disorder with psychotic feature (psychotic depression); delusional disorders (paranoia); shared psychotic disorder (shared paranoia disorder); brief psychotic disorder (other and unspecified reactive psychosis); psychotic disorder not otherwise specified (unspecified psychosis); paranoid personality disorder; schizoid personality disorder; schizotypal personality disorder; anxiety disorder; social anxiety disorder; substance ⁇ induced anxiety disorder; selective mutism; panic disorder; panic attacks; agoraphobia; attention deficit syndrome; post ⁇ traumatic stress disorder (PTSD); premenstrual dysphoric disorder (PMDD); and premenstrual syndrome (PMS).
  • depression depression
  • psychotic disorder schizophrenia
  • schizophreniform disorder acute schizophrenic episode
  • the disclosure provides a method for preventing and/or treating a brain disorder (e.g., Huntington's disease, Alzheimer's disease, dementia, and Parkinson's disease) by administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T
  • the disclosure provides a method for preventing and/or treating these disorders by administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇
  • the disclosure provides a method for preventing and/or treating an inflammation and/or pain by administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline
  • treatable “pain” includes nociceptive, neuropathic, and mix ⁇ type.
  • a method of the disclosure may reduce or alleviate the symptoms associated with inflammation, including but not limited to treating localized manifestation of inflammation characterized by acute or chronic swelling, pain, redness, increased temperature, or loss of function in some cases.
  • a method of the disclosure may reduce or alleviate the symptoms of pain regardless of the cause of the pain, including but not limited to reducing pain of varying severity, i.e., mild, moderate and severe pain, acute pain and chronic pain.
  • a method of the disclosure is effective in treating joint pain, muscle pain, tendon pain, burn pain, and pain caused by inflammation such as rheumatoid arthritis.
  • Skeletal or muscular diseases or conditions which may be treated include but are not limited to musculoskeletal sprains, musculoskeletal strains, tendinopathy, peripheral radiculopathy, osteoarthritis, joint degenerative disease, polymyalgia rheumatica, juvenile arthritis, gout, ankylosing spondylitis, psoriatic arthritis, systemic lupus erythematosus, costochondritis, tendonitis, bursitis, such as the common lateral epicondylitis (tennis elbow), medial epicondylitis (pitchers elbow) and trochanteric bursitis, temporomandibular joint syndrome, and fibromyalgia.
  • MAPKs provide a wide ⁇ ranging signaling cascade that allow cells to quickly respond to biotic and abiotic stimuli.
  • exemplary MAPKs include, but are not limited to, Tropomyosin Receptor Kinase A (TrkA), P38 ⁇ alpha, and c ⁇ Jun N ⁇ Terminal Kinase 3 (JNK3).
  • TrkA is a high affinity catalytic receptor of nerve growth factor (NGF) protein. TrkA regulates NGF response, influencing neuronal differentiation and outgrowth as well as programmed cell death.
  • NGF nerve growth factor
  • p38 ⁇ alpha is involved with the regulation of pro ⁇ inflammatory cytokines, including TNF ⁇ a.
  • JNK3 is a neuronal ⁇ specific protein isoform of the JNKs. It is involved with the regulation of apoptosis. JNK3 also plays a role in modulating the response of cytokines, growth factors, and oxidative stress.
  • modulating activity of a mitogen ⁇ activated protein kinase refers to changing, manipulating, and/or adjusting the activity of a mitogen ⁇ activated protein kinase. In one embodiment, modulating the activity of a MAPK can influence neural health, neurogenesis, neural growth and differentiation, and neurodegenerative diseases.
  • neurogenesis refers to changing, manipulating, and/or adjusting the growth and development of neural tissue.
  • neurogenesis comprises adult neurogenesis, in which new neural stem cells are generated from neural stem cells in an adult animal.
  • modulating neurogenesis comprises increasing and/or enhancing the rate at which new neural tissue is developed.
  • modulating neurite outgrowth refers to changing, manipulating, and/or adjusting the growth and development of neural projections, or “neurites.”
  • neurogenesis comprises modulating the growth of new neurites, the number of neurites per neuron, and/or neurite length.
  • modulating neurite outgrowth comprises increasing and/or enhancing the rate and/or length at which neurites develop.
  • the disorder is a male sexual dysfunction disorder. In some embodiments, the disorder is a female sexual dysfunction disorder.
  • compositions comprising an effective amount of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ M
  • the disclosure also relates to pharmaceutical compositions comprising a therapeutically effective amount of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ Me
  • a composition or a pharmaceutical composition of the disclosure may be in any form which contains 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO ⁇
  • the composition may be, for example, a tablet, capsule, liquid suspension, injectable, topical, or transdermal.
  • the compositions generally contain, for example, about 1% to about 99% by weight of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate
  • the composition may be between about 5% and about 75% by weight of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO ⁇ T ⁇ N
  • compositions comprising a combination of a first purified psilocybin derivative with a second purified psilocybin derivative, with one or two purified cannabinoids or with a purified terpene. Various ratios of these components in the composition are also disclosed.
  • the disclosures of US 2018/0221396 A1 and US 2019/0142851 A1 are incorporated herein by reference.
  • this disclosure provides a composition
  • a composition comprising: a first component comprising 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO
  • Such a composition may be a pharmaceutical composition wherein the components are present individually in therapeutically effective amounts or by combination in a therapeutically effective amount to treat a disease, disorder, or condition as described herein.
  • a first component comprising 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate,
  • compositions having as a first component 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Me
  • the first and second components can be administered at the same time (e.g., together in the same composition), or at separate times over the course of treating a patient in need thereof.
  • a composition may be a pharmaceutical composition wherein the components are present individually in therapeutically effective amounts or by combination in a therapeutically effective amount to treat a disease, disorder, or condition as described herein.
  • purified means separated from other materials, such as plant or fungal material, e.g., protein, chitin, cellulose, or water. In one embodiment, the term “purified” refers to a compound substantially free of other materials.
  • the term “purified” refers to a compound that is substantially free from a second tryptamine compound. In one embodiment, the term “purified” refers to a compound substantially free from histidine. In one embodiment, the term “purified” refers to a compound substantially free from a biological material, such as mold, fungus, plant matter, or bacteria. In one embodiment, the term “purified” refers to a compound substantially free from a paralytic. [122] In one embodiment, the term “purified” refers to a compound which has been separated from other compounds that are typically co ⁇ extracted when the purified compound is extracted from a naturally occurring organism.
  • a “purified” psilocybin derivative is partially or completely isolated from other psilocybin derivatives present in a source material, such as a psilocybin ⁇ containing mushroom.
  • “purified” baeocystin is substantially free from psilocybin and/or psilocin.
  • traditional psilocybin mushroom extracts aka crude extracts or fruit body extracts
  • unpurified psilocybin derivatives would include mycelium containing psilocybin derivatives and/or naturally occurring fungal material such as biological material and/or structural material such as chitin.
  • cannabidiol traditionally refers to whole plants (aka crude or full spectrum extracts) which have not been subjected to further purification to eliminate unwanted molecules that naturally occur in the cannabis plant.
  • a “cannabis extract comprising cannabidiol” could be expected to include cannabidiol (aka “CBD”) and also varying amounts of other compounds, including cannabinoids, terpenes, and other biological material.
  • the term “purified” refers to a compound or composition that has been crystallized.
  • the term “purified” refers to a compound or composition that has been chromatographed, for example by gas chromatography, liquid chromatography (e.g., LC, HPLC, etc.), etc.
  • the term “purified” refers to a compound or composition that has been distilled.
  • the term “purified” refers to a compound or composition that has been sublimed.
  • the term “purified” refers to a compound or composition that has been subject to two or more steps chosen from crystallization, chromatography, distillation, or sublimation.
  • the term “purified” refers to a compound that is between 80 ⁇ 100% pure. [129] In one embodiment, the term “purified” refers to a compound that is between 90 ⁇ 100% pure. [130] In one embodiment, the term “purified” refers to a compound that is between 95 ⁇ 100% pure. [131] In one embodiment, the term “purified” refers to a compound that is between 99 ⁇ 100% pure. [132] In one embodiment, the term “purified” refers to a compound that is between 99.9 ⁇ 100% pure.
  • a serotonergic drug refers to a compound that binds to, blocks, or otherwise influences (e.g., via an allosteric reaction) activity at a serotonin receptor as described in paragraphs [0245] ⁇ [0253] of US 2018/0221396 A1 and [0305] ⁇ [0311] US 2019/0142851 A1 as well as the disclosed exemplary embodiments.
  • Exemplary psilocybin derivatives include but are not limited to psilocybin itself and the psilocybin derivatives described in paragraphs [0081] ⁇ [0109] of US 2018/0221396 A1 and [0082] ⁇ [0110] US 2019/0142851 A1 as well as the disclosed exemplary embodiments.
  • Exemplary cannabinoids include but are not limited to the cannabinoids described in paragraphs [0111] ⁇ [0145] of US 2018/0221396 A1 and [0112] ⁇ [0146] US 2019/0142851 A1 as well as the disclosed exemplary embodiments.
  • Exemplary terpenes include but are not limited to the terpenes described in paragraphs [0160] ⁇ [0238] of US 2018/0221396 A1 and [0161] ⁇ [0300] US 2019/0142851 A1 as well as the disclosed exemplary embodiments.
  • a pharmaceutical formulation of the disclosure may comprise, consist essentially of, or consist of (a) 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO
  • a pharmaceutical formulation of the disclosure may comprise a composition containing 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO ⁇ T ⁇ N ⁇
  • compositions comprising a combination of a purified psilocybin derivative with a second purified psilocybin derivative, with one or two purified cannabinoids or with a purified terpene.
  • the disclosure provides a pharmaceutical formulation comprising as (a) 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO ⁇ T ⁇ N ⁇
  • a serotonergic drug refers to a compound that binds to, blocks, or otherwise influences (e.g., via an allosteric reaction) activity at a serotonin receptor as described in paragraphs [0245] ⁇ [0253] of US 2018/0221396 A1 and [0305] ⁇ [0311] US 2019/0142851 A1 as well as the disclosed exemplary embodiments.
  • Some exemplary serotonergic drugs include SSRIs and SNRIs.
  • serotonergic drugs include the following molecules, including any salts, solvates, or polymorphs thereof: 6 ⁇ allyl ⁇ N,N ⁇ diethyl ⁇ NL; N,N ⁇ dibutyl ⁇ T; N,N ⁇ diethyl ⁇ T; N,N ⁇ diisopropyl ⁇ T; 5 ⁇ methyoxy ⁇ alpha ⁇ methyl ⁇ T; N,N ⁇ dimethyl ⁇ T; 2,alpha ⁇ dimethyl ⁇ T; alpha,N ⁇ dimethyl ⁇ T; N,N ⁇ dipropyl ⁇ T; N ⁇ ethyl ⁇ N ⁇ isopropyl ⁇ T; alpha ⁇ ethyl ⁇ T; 6 ⁇ N,N ⁇ Triethyl ⁇ NL; 3,4 ⁇ dihydro ⁇ 7 ⁇ methoxy ⁇ 1 ⁇ methyl ⁇ C; 7 ⁇ methyoxy ⁇ 1 ⁇ methyl ⁇ C; N,N ⁇ dibutyl ⁇ 4 ⁇ hydroxy ⁇ T; N,N ⁇ diethyl ⁇ 4 ⁇ hydroxy ⁇ T; N,N ⁇ diisopropyl
  • a serotonergic drug is chosen from alprazolam, amphetamine, aripiprazole, azapirone, a barbiturate, bromazepam, bupropion, buspirone, a cannabinoid, chlordiazepoxide, citalopram, clonazepam, clorazepate, dextromethorphan, diazepam, duloxetine, escitalopram, fluoxetine, flurazepam, fluvoxamine, lorazepam, lysergic acid diethylamide, lysergamide, 3,4 ⁇ methylenedioxymethamphetamine, milnacipran, mirtazapine, naratriptan, paroxetine, pethidine, phene
  • the serotonergic drug is 3,4 ⁇ methylenedioxymethamphetamine.
  • Exemplary psilocybin derivatives include but are not limited to psilocybin itself and the psilocybin derivatives described in paragraphs [0081] ⁇ [0109] of US 2018/0221396 A1 and [0082] ⁇ [0110] US 2019/0142851 A1 as well as the disclosed exemplary embodiments, incorporated here by reference.
  • compositions disclosed herein comprise one or more purified psilocybin derivatives chosen from: [3 ⁇ (2 ⁇ dimethylaminoethyl) ⁇ 1H ⁇ indol ⁇ 4 ⁇ yl] dihydrogen phosphate; 4 ⁇ hydroxytryptamine; 4 ⁇ hydroxy ⁇ N,N ⁇ dimethyltryptamine; [3 ⁇ (2 ⁇ methylaminoethyl) ⁇ 1H ⁇ indol ⁇ 4 ⁇ yl] dihydrogen phosphate; 4 ⁇ hydroxy ⁇ N ⁇ methyltryptamine; [3 ⁇ (aminoethyl) ⁇ 1H ⁇ indol ⁇ 4 ⁇ yl] dihydrogen phosphate; [3 ⁇ (2 ⁇ trimethylaminoethyl) ⁇ 1H ⁇ indol ⁇ 4 ⁇ yl] dihydrogen phosphate; and 4 ⁇ hydroxy ⁇ N,N,N ⁇ trimethyltryptamine.
  • purified psilocybin derivatives chosen from: [3 ⁇ (2 ⁇ dimethylaminoethyl)
  • Exemplary cannabinoids include but are not limited to the cannabinoids described in paragraphs [0111] ⁇ [0145] of US 2018/0221396 A1 and [0112] ⁇ [0146] US 2019/0142851 A1 as well as the disclosed exemplary embodiments.
  • cannabinoids within the context of this disclosure include the following molecules: cannabichromene (CBC); cannabichromenic acid (CBCA); cannabichromevarin (CBCV); cannabichromevarinic acid (CBCVA); cannabicyclol (CBL); cannabicyclolic acid (CBLA); cannabicyclovarin (CBLV); cannabidiol (CBD); cannabidiol monomethylether (CBDM); cannabidiolic acid (CBDA); cannabidiorcol (CBD ⁇ C1); cannabidivarin (CBDV); cannabidivarinic acid (CBDVA); cannabielsoic acid B (CBEA ⁇ B); cannabielsoin (CBE); cannabielsoin acid A (CBEA ⁇ A); cannabigerol (CBG); cannabigerol monomethylether (CBGM); cannabigerolic acid (CBGA); cannabigerolic acid
  • the purified cannabinoid is chosen from THC, THCA, THCV, THCVA, CBC, CBCA, CBCV, CBCVA, CBD, CBDA, CBDV, CBVD, CBDVA, CBG, CBGA, CBGV, or CBGVA.
  • Exemplary terpenes include but are not limited to the terpenes described in paragraphs [0160] ⁇ [0238] of US 2018/0221396 A1 and [0161] ⁇ [0300] US 2019/0142851 A1 as well as the disclosed exemplary embodiments.
  • a purified terpene is chosen from acetanisole, acetyl cedrene, anethole, anisole, benzaldehyde, bornyl acetate, borneol, cadinene, cafestol, caffeic acid, camphene, camphor, capsaicin, carene, carotene, carvacrol, carvone, caryophyllene, caryophyllene, caryophyllene oxide, cedrene, cedrene epoxide, cecanal, cedrol, cembrene, cinnamaldehyde, cinnamic acid, citronellal, citronellol, cymene, eicosane, elemene, estragole, ethyl acetate, ethyl cinnamate, ethyl maltol, eucalyptol/1,8 ⁇ cineole, eudesmol
  • a purified terpene is chosen from bornyl acetate, alpha ⁇ bisabolol, borneol, camphene, camphor, carene, caryophyllene, cedrene, cymene, elemene, eucalyptol, eudesmol, farnesene, fenchol, geraniol, guaiacol, humulene, isoborneol, limonene, linalool, menthol, myrcene, nerolidol, ocimene, phellandrene, phytol, pinene, pulegone, sabinene, terpineol, terpinolene, or valencene.
  • adrenergic drug refers to a compound that binds, blocks, or otherwise influences (e.g., via an allosteric reaction) activity at an adrenergic receptor.
  • an adrenergic drug binds to an adrenergic receptor.
  • an adrenergic drug indirectly affects an adrenergic receptor, e.g., via interactions affecting the reactivity of other molecules at the adrenergic receptor.
  • an adrenergic drug is an agonist, e.g., a compound activating an adrenergic receptor.
  • an adrenergic drug is an antagonist, e.g., a compound binding but not activating an adrenergic receptor, e.g., blocking a receptor.
  • an adrenergic drug is an effector molecule, e.g., a compound binding to an enzyme for allosteric regulation.
  • an adrenergic drug acts (either directly or indirectly) at more than one type of receptor (e.g., 5HT, dopamine, adrenergic, acetylcholine, etc.).
  • an adrenergic drug is an antidepressant.
  • an adrenergic drug is a norepinephrine transporter inhibitor. In one embodiment, an adrenergic drug is a vesicular monoamine transporter inhibitor. In one embodiment, an adrenergic drug is chosen from adrenaline, agmatine, amoxapine, aptazapine, atomoxetine, bupropion, clonidine, doxepin, duloxetine, esmirtazpine, mianserin, ketanserin, mirabegron, mirtazapine, norepinephrine, phentolamine, phenylephrine, piperoxan, reserpine, ritodrine, setiptiline, tesofensine, timolol, trazodone, trimipramine, or xylazine.
  • the term “dopaminergic drug” refers to a compound that binds, blocks, or otherwise influences (e.g., via an allosteric reaction) activity at a dopamine receptor.
  • a dopaminergic drug binds to a dopamine receptor.
  • a dopaminergic drug indirectly affects a dopamine receptor, e.g., via interactions affecting the reactivity of other molecules at the dopamine receptor.
  • a dopaminergic drug is an agonist, e.g., a compound activating a dopamine receptor.
  • a dopaminergic drug is an antagonist, e.g., a compound binding but not activating a dopamine receptor, e.g., blocking a receptor.
  • a dopaminergic drug is an effector molecule, e.g., a compound binding to an enzyme for allosteric regulation.
  • a dopaminergic drug acts (either directly or indirectly) at more than one type of receptor (e.g., 5HT, dopamine, adrenergic, acetylcholine, etc.).
  • a dopaminergic drug is a dopamine transporter inhibitor.
  • a dopaminergic drug is a vesicular monoamine transporter inhibitor.
  • a dopaminergic drug is chosen from amineptine, apomorphine, benzylpiperazine, bromocriptine, cabergoline, chlorpromazine, clozapine, dihydrexidine, domperidone, dopamine, fluphenazine, haloperidol, ketamine, loxapine, methamphetamine, olanzapine, pemoline, perphenazine, pergolide, phencyclidine, phenethylamine, phenmetrazine, pimozide, piribedil, a psychostimulant, reserpine, risperidone, ropinirole, tetrabenazine, or thioridazine.
  • a MAOI refers to a compound that blocks the actions of monoamine oxidase enzymes.
  • a MAOI inhibits the activity of one or both monoamine oxidase A and monoamine oxidase B.
  • a MAOI is a reversible inhibitor of monoamine oxidase A.
  • a MAOI is a drug chosen from isocarboxazid, phenelzine, or tranylcypromine.
  • a MAOI is ⁇ carboline, pinoline, harmane, harmine, harmaline, harmalol, tetrahydroharmine, 9 ⁇ methyl ⁇ carboline, or 3 ⁇ carboxy ⁇ tetrahydrononharman.
  • the compositions and methods disclosed herein include one or more purified erinacine molecules.
  • the compositions and methods disclosed herein comprise purified erinacine A.
  • the compositions and methods disclosed herein comprise erinacine B.
  • the compositions and methods disclosed herein comprise erinacine C.
  • the compositions and methods disclosed herein comprise erinacine D.
  • compositions and methods disclosed herein comprise erinacine E. In one embodiment, the compositions and methods disclosed herein comprise erinacine F. In one embodiment, the compositions and methods disclosed herein comprise erinacine G. In one embodiment, the compositions and methods disclosed herein comprise erinacine H. In one embodiment, the compositions and methods disclosed herein comprise erinacine I. In one embodiment, the compositions and methods disclosed herein comprise erinacine J. In one embodiment, the compositions and methods disclosed herein comprise erinacine K In one embodiment, the compositions and methods disclosed herein comprise erinacine P. In one embodiment, the compositions and methods disclosed herein comprise erinacine Q. In one embodiment, the compositions and methods disclosed herein comprise erinacine R.
  • compositions and methods disclosed herein comprise erinacine S.
  • the compositions and methods disclosed herein include one or more purified hericenone molecules.
  • the compositions and methods disclosed herein comprise purified hericenone A.
  • the compositions and methods disclosed herein comprise purified hericenone B.
  • the compositions and methods disclosed herein comprise purified hericenone C.
  • the compositions and methods disclosed herein comprise purified hericenone D.
  • the compositions and methods disclosed herein comprise purified hericenone E.
  • the compositions and methods disclosed herein comprise purified hericenone F.
  • compositions and methods disclosed herein comprise purified hericenone G. In one embodiment, the compositions and methods disclosed herein comprise purified hericenone H.
  • the actual amount required for treatment of any particular patient may depend upon a variety of factors including, for example, the disease being treated and its severity; the specific pharmaceutical composition employed; the age, body weight, general health, sex, and diet of the patient; the mode of administration; the time of administration; the route of administration; and the rate of excretion; the duration of the treatment; any drugs used in combination or coincidental with the specific compound employed; and other such factors well known in the medical arts. These factors are discussed in Goodman and Gilman’s “The Pharmacological Basis of Therapeutics,” Tenth Edition, A. Gilman, J. Hardman and L. Limbird, eds., McGraw ⁇ Hill Press, 155 ⁇ 173 (2001), which is incorporated herein by reference.
  • the pharmaceutically acceptable carrier may be chosen from any one or a combination of carriers known in the art. The choice of the pharmaceutically acceptable carrier depends upon the pharmaceutical form and the desired method of administration to be used.
  • Exemplary carriers include those that do not substantially alter the structure or activity of 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇ T hydrophthalate, crystalline 5 ⁇ Cl ⁇ T hydrophthalate, 5 ⁇ Cl ⁇ T malate, crystalline 5 ⁇ Cl ⁇ T malate, 5 ⁇ MeO ⁇ T ⁇ N ⁇ Su
  • compositions of the disclosure may be prepared by methods know in the pharmaceutical formulation art, for example, see Remington’s Pharmaceutical Sciences, 18th Ed., (Mack Publishing Company, Easton, Pa., 1990), which is incorporated herein by reference.
  • a solid dosage form 5 ⁇ MeO ⁇ T fumarate, crystalline 5 ⁇ MeO ⁇ T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4 ⁇ MeO ⁇ MiPT fumarate, crystalline 4 ⁇ MeO ⁇ MiPT fumarate, 4 ⁇ HO ⁇ PiPT hydrofumarate, crystalline 4 ⁇ HO ⁇ PiPT hydrofumarate, 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, crystalline 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, 5 ⁇ Cl ⁇ T hydromaleate, crystalline 5 ⁇ Cl ⁇ T hydromaleate, 5 ⁇ Cl ⁇
  • the dosage forms may also comprise buffering agents.
  • the excipient is not water.
  • the excipient is not a solvent (e.g., EtOH, diethyl ether, ethyl acetate, or hydrocarbon ⁇ based solvents (e.g., hexanes).
  • the dosage form is substantially free of water and/or solvents, for example less than about 5% water by mass, less than 2% water by mass, less than 1% water by mass, less than 0.5% water by mass, or less than 0.1% water by mass.
  • Excipients or pharmaceutically acceptable adjuvants known in the pharmaceutical formulation art may also be used in the pharmaceutical compositions of the disclosure.
  • microorganisms include, but are not limited to, preserving, wetting, suspending, sweetening, flavoring, perfuming, emulsifying, and dispensing agents.
  • Prevention of the action of microorganisms may be ensured by inclusion of various antibacterial and antifungal agents, for example, parabens, chlorobutanol, phenol, sorbic acid, and the like. It may also be desirable to include isotonic agents, for example, sugars, sodium chloride, and the like.
  • a pharmaceutical composition of the disclosure may also contain minor amounts of auxiliary substances such as wetting or emulsifying agents, pH buffering agents, antioxidants, and the like, such as, for example, citric acid, sorbitan monolaurate, triethanolamine oleate, butylated hydroxytoluene, etc.
  • auxiliary substances such as wetting or emulsifying agents, pH buffering agents, antioxidants, and the like, such as, for example, citric acid, sorbitan monolaurate, triethanolamine oleate, butylated hydroxytoluene, etc.
  • Solid dosage forms as described above may be prepared with coatings and shells, such as enteric coatings and others well known in the art. They may contain pacifying agents and can also be of such composition that they release the active compound or compounds in a certain part of the intestinal tract in a delayed manner.
  • Non ⁇ limiting examples of embedded compositions that may be used are polymeric substances and waxes.
  • the active compounds may also be in microencapsulated form, if appropriate, with one or more of the above ⁇ mentioned excipients.
  • Suspensions in addition to the active compounds, may contain suspending agents, such as, for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar ⁇ agar and tragacanth, or mixtures of these substances, and the like.
  • suspending agents such as, for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar ⁇ agar and tragacanth, or mixtures of these substances, and the like.
  • Solid dosage forms for oral administration which includes capsules, tablets, pills, powders, and granules, may be used.
  • the active compound may be mixed with at least one inert, pharmaceutically acceptable excipient (also known as a pharmaceutically acceptable carrier).
  • pharmaceutically acceptable excipient also known as a pharmaceutically acceptable carrier.
  • administration may be, for example, orally, buccally, nasally, parenterally (intravenous, intramuscular, or subcutaneous), topically, transdermally, intravaginally, intravesically, or intrasystemically, in the form of solid, semi ⁇ solid, lyophilized powder, or liquid dosage forms, such as, for example, tablets, suppositories, pills, soft elastic and hard gelatin capsules, powders, solutions, suspensions, or aerosols, or the like, such as, for example, in unit dosage forms suitable for simple administration of precise dosages.
  • One route of administration may be oral administration, using a convenient daily dosage regimen that can be adjusted according to the degree of severity of the disease ⁇ state to be treated.
  • E5. A composition comprising 5 ⁇ methoxytryptammonium fumarate according to E1 and an excipient.
  • E6 A composition comprising crystalline 5 ⁇ methoxytryptammonium fumarate according to any one of E2 ⁇ E4 and an excipient.
  • E7 A composition comprising crystalline 5 ⁇ methoxytryptammonium fumarate according to any one of E2 ⁇ E4 and an excipient.
  • a composition comprising 5 ⁇ methoxytryptammonium fumarate according to E1 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [165] E8.
  • a composition comprising crystalline 5 ⁇ methoxytryptammonium fumarate according to any one of E2 ⁇ E4 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [166] E9.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ methoxytryptammonium fumarate according to E1.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ methoxytryptammonium fumarate according to any one of E2 ⁇ E4.
  • E11 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E5 or E7. [169] E12.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E6 or E8.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ methoxytryptammonium fumarate according to E1.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ methoxytryptammonium fumarate according to any one of E2 ⁇ E4.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E5 or E7.
  • E16 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E6 or E8.
  • E18 E18.
  • a composition comprising tryptammonium hydromalate according to E17 and an excipient.
  • E22 A composition comprising crystalline tryptammonium hydromalate according to any one of E18 ⁇ E20 and an excipient.
  • E23 A composition comprising crystalline tryptammonium hydromalate according to any one of E18 ⁇ E20 and an excipient.
  • a composition comprising tryptammonium hydromalate according to E17 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [181] E24.
  • a composition comprising crystalline tryptammonium hydromalate according to any one of E18 ⁇ E20 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [182] E25.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of tryptammonium hydromalate according to E17.
  • E26 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline tryptammonium hydromalate according to any one of E18 ⁇ E20.
  • E27 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E21 or E23. [185] E28.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E22 or E24.
  • E29. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of tryptammonium hydromalate according to E17.
  • E30. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline tryptammonium hydromalate according to any one of E18 ⁇ E20. [188] E31.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E21 or E23.
  • E32. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E22 or E24.
  • E33. 2 ⁇ (1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 2 ⁇ carboxybenzoate (tryptammonium hydrophthalate).
  • E34 Crystalline 2 ⁇ (1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 2 ⁇ carboxybenzoate (tryptammonium hydrophthalate).
  • E37 A composition comprising tryptammonium hydrophthalate according to E33 and an excipient.
  • E38 A composition comprising crystalline tryptammonium hydrophthalate according to any one of E34 ⁇ E36 and an excipient.
  • a composition comprising tryptammonium hydrophthalate according to E33 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [197] E40.
  • a composition comprising crystalline tryptammonium hydrophthalate according to any one of E34 ⁇ E36 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [198] E41.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of tryptammonium hydrophthalate according to E33.
  • E42. A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline tryptammonium hydrophthalate according to any one of E34 ⁇ E36.
  • E43. A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E37 or E39.
  • E44 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E37 or E39.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E38 or E40.
  • E45 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of tryptammonium hydrophthalate according to E33.
  • E46 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline tryptammonium hydrophthalate according to any one of E34 ⁇ E36.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E37 or E39.
  • E48. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E38 or E40.
  • E49. Bis([2 ⁇ (4 ⁇ methoxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl](methyl)(propan ⁇ 2 ⁇ yl)azanium) (2E) ⁇ but ⁇ 2 ⁇ enedioate (4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate).
  • E52 Crystalline bis([2 ⁇ (4 ⁇ methoxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl](methyl)(propan ⁇ 2 ⁇ yl)azanium)
  • E53 A composition comprising 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate according to E49 and an excipient.
  • E54 A composition comprising crystalline 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate according to any one of E50 ⁇ E52 and an excipient.
  • E55 A composition comprising crystalline 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate according to any one of E50 ⁇ E52 and an excipient.
  • a composition comprising 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate according to E49 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [213] E56.
  • a composition comprising crystalline 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate according to any one of E50 ⁇ E52 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [214] E57.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate according to E49.
  • E58. A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate according to any one of E50 ⁇ E52.
  • E59 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E53 or E55.
  • E60 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E54 or E56.
  • E61 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate according to E49. [219] E62.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptammonium fumarate according to any one of E50 ⁇ E52.
  • E63 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E53 or E55.
  • E64. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E54 or E56. [222] E65.
  • E68 A composition comprising crystalline 4 ⁇ hyroxy ⁇ N ⁇ propyl ⁇ N ⁇ isopropyltryptammnonium hydrofumarate according to any one of E65 ⁇ E67 and an excipient. [226] E69.
  • a composition comprising crystalline 4 ⁇ hyroxy ⁇ N ⁇ propyl ⁇ N ⁇ isopropyltryptammnonium hydrofumarate according to any one of E65 ⁇ E67 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [227] E70.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 4 ⁇ hyroxy ⁇ N ⁇ propyl ⁇ N ⁇ isopropyltryptammnonium hydrofumarate according to any one of E65 ⁇ E67. [228] E71. A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E68 or E69. [229] E72.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 4 ⁇ hyroxy ⁇ N ⁇ propyl ⁇ N ⁇ isopropyltryptammnonium hydrofumarate according to any one of E65 ⁇ E67.
  • E73 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E68 or E69. [231] E74.
  • E78 A composition comprising 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium according to E74 and an excipient.
  • E79 A composition comprising crystalline 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium according to any one of E75 ⁇ E77 and an excipient.
  • a composition comprising 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium according to E74 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [238] E81.
  • a composition comprising crystalline 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium according to any one of E75 ⁇ E77 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [239] E82.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium according to E74.
  • E83 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium according to any one of E75 ⁇ E77.
  • E84 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E78 or E80.
  • E85 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E79 or E81.
  • E86 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium according to E74. [244] E87.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ chlorotryptammonium N ⁇ succinyl ⁇ 5 ⁇ chlorotryptammonium according to any one of E75 ⁇ E77.
  • E88. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E78 or E80.
  • E89 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E79 or E81. [247] E90.
  • a composition comprising 5 ⁇ chlorotryptammonium hydromaleate according to E90 and an excipient.
  • E95 A composition comprising crystalline 5 ⁇ chlorotryptammonium hydromaleate according to any one of E91 ⁇ E93 and an excipient.
  • E96 E96.
  • a composition comprising 5 ⁇ chlorotryptammonium hydromaleate according to E90 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [254] E97.
  • a composition comprising crystalline 5 ⁇ chlorotryptammonium hydromaleate according to any one of E91 ⁇ E93 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [255] E98.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ chlorotryptammonium hydromaleate according to E90.
  • E99 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ chlorotryptammonium hydromaleate according to any one of E91 ⁇ E93.
  • E100 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E94 or E96. [258] E101.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E95 or E97.
  • E102. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ chlorotryptammonium hydromaleate according to E90.
  • E103. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ chlorotryptammonium hydromaleate according to any one of E91 ⁇ E93. [261] E104.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E94 or E96.
  • E105 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E95 or E97.
  • E106 2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 2 ⁇ carboxybenzoate (5 ⁇ chlorotryptammonium hydrophthalate).
  • E107 2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium 2 ⁇ carboxybenzoate (5 ⁇ chlorotryptammonium hydrophthalate).
  • E110 A composition comprising 5 ⁇ chlorotryptammonium hydrophthalate according to E106 and an excipient.
  • E111 A composition comprising crystalline 5 ⁇ chlorotryptammonium hydrophthalate according to any one of E107 ⁇ E109 and an excipient.
  • a composition comprising 5 ⁇ chlorotryptammonium hydrophthalate according to E106 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [270] E113.
  • a composition comprising crystalline 5 ⁇ chlorotryptammonium hydrophthalate according to any one of E107 ⁇ E109 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [271] E114.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ chlorotryptammonium hydrophthalate according to E106.
  • E115 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ chlorotryptammonium hydrophthalate according to any one of E107 ⁇ E109.
  • E116 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E110 or E112. [274] E117.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E111 or E113.
  • E118. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ chlorotryptammonium hydrophthalate according to E106.
  • E119. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ chlorotryptammonium hydrophthalate according to any one of E107 ⁇ E109. [277] E120.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E110 or E112.
  • E121 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E111 or E113.
  • E122 Bis(2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium) 2 ⁇ hydroxybutanedioate (5 ⁇ chlorotryptammonium malate).
  • E123 Bis(2 ⁇ (5 ⁇ chloro ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethan ⁇ 1 ⁇ aminium) 2 ⁇ hydroxybutanedioate (5 ⁇ chlorotryptammonium malate).
  • a composition comprising 5 ⁇ chlorotryptammonium malate according to E122 and an excipient.
  • E127 A composition comprising crystalline 5 ⁇ chlorotryptammonium malate according to any one of E123 ⁇ E125 and an excipient.
  • E128 A composition comprising 5 ⁇ chlorotryptammonium malate according to any one of E123 ⁇ E125 and an excipient.
  • a composition comprising 5 ⁇ chlorotryptammonium malate according to E122 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [286] E129.
  • a composition comprising crystalline 5 ⁇ chlorotryptammonium malate according to any one of E123 ⁇ E125 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [287] E130.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ chlorotryptammonium malate according to E122.
  • E131 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ chlorotryptammonium malate according to any one of E123 ⁇ E125.
  • E132 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E126 or E128. [290] E133.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E127 or E129.
  • E134 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ chlorotryptammonium malate according to E122.
  • E135. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ chlorotryptammonium malate according to any one of E123 ⁇ E125. [293] E136.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E126 or E128. [294] E137. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E127 or E129. [295] E138.
  • E142 A composition comprising 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium according to E138 and an excipient.
  • E143 A composition comprising crystalline 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium according to any one of E139 ⁇ E141 and an excipient.
  • E144 A composition comprising crystalline 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium according to any one of E139 ⁇ E141 and an excipient.
  • a composition comprising 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium according to E138 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [302] E145.
  • a composition comprising crystalline 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium according to any one of E139 ⁇ E141 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [303] E146.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium according to E138.
  • E147. A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium according to any one of E139 ⁇ E141.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E142 and E144.
  • E149 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E143 and E145.
  • E150 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium according to E138. [308] E151.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ methoxytryptammonium N ⁇ succinyl ⁇ 5 ⁇ methoxytryptammonium according to any one of E139 ⁇ E141.
  • E152 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E142 or E144.
  • E153 A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E143 or E145. [311] E154.
  • a composition comprising crystalline 5 ⁇ methyltryptamine according to any one of 154 ⁇ E156 and an excipient.
  • E158 A composition comprising crystalline 5 ⁇ methyltryptamine according to any one of E154 ⁇ E156 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.
  • E159 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ methyltryptamine according to any one of E154 ⁇ E156.
  • E160 A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E157 or E158.
  • E161. A method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 5 ⁇ methyltryptamine according to any one of E154 ⁇ E156. [319] E162.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E157 or E158.
  • E163. Crystalline bis(N ⁇ [2 ⁇ (4 ⁇ hydroxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl] ⁇ N ⁇ methylcyclopropanaminium) (2E) ⁇ but ⁇ 2 ⁇ enedioate (4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropyltryptammonium fumarate). [321] E164.
  • E166 A composition comprising crystalline 4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropyltryptammonium fumarate according to any one of E163 ⁇ E165 and an excipient. [324] E167.
  • a composition comprising crystalline 4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropyltryptammonium fumarate according to any one of E163 ⁇ E165 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [325] E168.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropyltryptammonium fumarate according to any one of E163 ⁇ E165. [326] E169. A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E166 or E167. [327] E170.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 4 ⁇ hydroxy ⁇ N ⁇ methyl ⁇ N ⁇ cyclopropyltryptammonium fumarate according to any one of E163 ⁇ E165. [328] E171.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E166 or E167. [329] E172.
  • Crystalline [2 ⁇ (4 ⁇ hydroxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl]bis(propan ⁇ 2 ⁇ yl)azanium (2E) ⁇ 3 ⁇ carboxyprop ⁇ 2 ⁇ enoate (4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate). [330] E173. Crystalline form 1 of [2 ⁇ (4 ⁇ hydroxy ⁇ 1H ⁇ indol ⁇ 3 ⁇ yl)ethyl]bis(propan ⁇ 2 ⁇ yl)azanium (2E) ⁇ 3 ⁇ carboxyprop ⁇ 2 ⁇ enoate (4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate). [331] E174.
  • E175. A composition comprising crystalline 4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate according to any one of E172 ⁇ E174 and an excipient. [333] E176.
  • a composition comprising crystalline 4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate according to any one of E172 ⁇ E174 as a first component and a second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone. [334] E177.
  • a method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate according to any one of E172 ⁇ E174. [335] E178. A method of preventing or treating a psychological disorder comprising the step of: administering to a subject in need thereof a composition according to E175 or E176. [336] E179.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a therapeutically effective amount of crystalline 4 ⁇ hydroxy ⁇ N,N ⁇ diisopropyltryptammonium hydrofumarate according to any one of E172 ⁇ E174. [337] E180.
  • a method of preventing or treating inflammation and/or pain comprising the step of: administering to a subject in need thereof a composition according to E175 or E176.
  • Crystallization Single crystals suitable for X ⁇ ray diffraction studies were grown from the slow evaporation of a methanol solution.
  • Single Crystal Characterization [360] The single crystal data and structure refinement parameters for the crystalline form 1 structure of tryptammonium hydrophthalate are reported in Table 3a, below.
  • Synthesis [363] 100 mg of 4 ⁇ methoxy ⁇ N ⁇ methyl ⁇ N ⁇ isopropyltryptamine hydrofumarate and 104 mg of lead (II) acetate were dissolved in 15 mL of distilled water and allowed to stir for one hour.
  • the data for crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fumarate in Table 3a relates to the asymmetric unit.
  • Crystallization Single crystals suitable for X ⁇ ray diffraction studies were grown from the slow evaporation of a dichloromethane solution.
  • Single Crystal Characterization [414] The single crystal data and structure refinement parameters for the crystalline form 1 structure of 5 ⁇ Me ⁇ T are reported in Table 3b, below.
  • Preparation and Characterization of Crystalline form 1 of 4 ⁇ HO ⁇ MCPT fumarate [416] Crystallization [417] Crystals suitable for single crystal X ⁇ ray diffraction studies were grown from the slow evaporation of a commercial sample (The Indole Shop).
  • FIG. 1 shows the molecular structure of crystalline form 1 of 5 ⁇ MeO ⁇ T fumarate, showing the atomic labeling.
  • FIG. 2 shows the molecular structure of crystalline form 1 of tryptammonium hydromalate, showing the atomic labeling.
  • FIG. 3 shows the molecular structure of crystalline form 1 of tryptammonium hydrophthalate, showing the atomic labeling.
  • FIG. 28 shows the molecular structure of crystalline form 1 of tryptammonium hydrophthalate, showing the atomic labeling.
  • FIG. 4 shows the molecular structure of crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fumarate, showing the atomic labeling.
  • FIG. 5 shows the molecular structure of crystalline form 1 of 4 ⁇ HO ⁇ PiPT hydrofumarate, showing the atomic labeling.
  • FIG. 6 shows the molecular structure of crystalline form 1 of 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T, showing the atomic labeling.
  • FIG. 7 shows the molecular structure of crystalline form 1 of 5 ⁇ Cl ⁇ T hydromaleate, showing the atomic labeling.
  • FIG. 8 shows the molecular structure of crystalline form 1 of 5 ⁇ Cl ⁇ T hydrophthalate, showing the atomic labeling.
  • FIG. 9 shows the molecular structure of crystalline form 1 of 5 ⁇ Cl ⁇ T malate, showing the atomic labeling.
  • FIG. 10 shows the molecular structure of crystalline form 1 of 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T, showing the atomic labeling.
  • FIG. 11 shows the molecular structure of crystalline form 1 of 5 ⁇ Me ⁇ T, showing the atomic labeling.
  • FIG. 12 shows the molecular structure of crystalline form 1 of 4 ⁇ HO ⁇ MCPT fumarate, showing the atomic labeling.
  • FIG. 13 shows the molecular structure of crystalline form 1 of 4 ⁇ HO ⁇ DiPT hydrofumarate, showing the atomic labeling.
  • FIG. 14 shows the unit cell of crystalline form 1 of 5 ⁇ MeO ⁇ T fumarate along the a ⁇ axis.
  • FIG. 15 shows the unit cell of crystalline form 1 of tryptammonium hydromalate along the a ⁇ axis.
  • FIG. 16 shows the unit cell of crystalline form 1 of tryptammonium hydrophthalate along the b ⁇ axis.
  • FIG. 17 shows the unit cell of crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fumarate along the c ⁇ axis.
  • FIG. 18 shows the unit cell of crystalline form 1 of 4 ⁇ HO ⁇ PiPT hydrofumarate along the a ⁇ axis. [443] FIG.
  • FIG. 19 shows the unit cell of crystalline form 1 of 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T along the a ⁇ axis.
  • FIG. 20 shows the unit cell of crystalline form 1 of 5 ⁇ Cl ⁇ T hydromaleate along the b ⁇ axis.
  • FIG. 21 shows the unit cell of crystalline form 1 of 5 ⁇ Cl ⁇ T hydrophthalate along the c ⁇ axis.
  • FIG. 22 shows the unit cell of crystalline form 1 of 5 ⁇ Cl ⁇ T malate along the a ⁇ axis.
  • FIG. 23 shows the unit cell of crystalline form 1 of 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T along the a ⁇ axis.
  • FIG. 24 shows the unit cell of crystalline form 1 of 5 ⁇ Me ⁇ T along the a ⁇ axis.
  • FIG. 25 shows the unit cell of crystalline form 1 of 4 ⁇ HO ⁇ MCPT fumarate along the b ⁇ axis.
  • FIG. 26 shows the unit cell of crystalline form 1 of 4 ⁇ HO ⁇ DiPT hydrofumarate along the a ⁇ axis.
  • FIG. 27 shows the 2:1 ratio of crystalline form 1 of 5 ⁇ MeO ⁇ T fumarate as a dimer.
  • FIG. 28 shows the 2:1 ratio of crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fumarate as a dimer.
  • FIG. 3 shows the unit cell of crystalline form 1 of 5 ⁇ Me ⁇ T along the a ⁇ axis.
  • FIG. 30 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ MeO ⁇ T fumarate generated from its single crystal data.
  • Table 4 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 30. The entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 7.3, 12.5, and 24.8 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 30.
  • Simulated Powder X ⁇ ray Diffraction (PXRD) Pattern [457]
  • FIG. 31 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of tryptammonium hydromalate generated from its single crystal data. Table 5 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 31.
  • the entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 7.1, 11.3, and 20.9 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 31.
  • Simulated Powder X ⁇ ray Diffraction (PXRD) Pattern [459]
  • FIG. 32 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of tryptammonium hydrophthalate generated from its single crystal data.
  • Table 6 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 32.
  • the entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 6.0, 11.2, and 15.4 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 32.
  • Simulated Powder X ⁇ ray Diffraction (PXRD) Pattern [461] FIG.
  • XRPD simulated X ⁇ ray powder diffraction pattern
  • Table 7 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 33.
  • the entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 9.1, 14.5, and 16.0 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 33.
  • FIG. 34 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 4 ⁇ HO ⁇ PiPT hydrofumarate generated from its single crystal data.
  • Table 8 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 34. The entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 11.1, 12.0, and 15.8 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 34.
  • Simulated Powder X ⁇ ray Diffraction (PXRD) Pattern [465]
  • FIG. 35 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T generated from its single crystal data. Table 9 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG.
  • FIG. 35 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ Cl ⁇ T hydromaleate generated from its single crystal data.
  • Table 10 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 36.
  • the entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 9.2, 10.6, and 14.8 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 36.
  • Simulated Powder X ⁇ ray Diffraction (PXRD) Pattern [469] FIG.
  • XRPD X ⁇ ray powder diffraction pattern
  • Table 11 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 37.
  • the entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 11.3, 12.3, and 15.4 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 37.
  • FIG. 38 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ Cl ⁇ T malate generated from its single crystal data.
  • Table 12 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 38. The entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 12.5, 13.2, and 14.3 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 38.
  • Simulated Powder X ⁇ ray Diffraction (PXRD) Pattern [473]
  • FIG. 39 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T generated from its single crystal data. Table 13 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG.
  • FIG. 40 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 5 ⁇ Me ⁇ T generated from its single crystal data.
  • Table 14 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 40.
  • the entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 13.4, 15.5, and 19.5 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 40.
  • Simulated Powder X ⁇ ray Diffraction (PXRD) Pattern [477] FIG.
  • XRPD simulated X ⁇ ray powder diffraction pattern
  • Table 15 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 41.
  • the entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 9.6, 10.7, and 16.6 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 41.
  • FIG. 42 shows a simulated X ⁇ ray powder diffraction pattern (XRPD) for crystalline form 1 of 4 ⁇ HO ⁇ DiPT hydrofumarate generated from its single crystal data.
  • Table 16 lists the angles, °2 ⁇ ⁇ 0.2°2 ⁇ , and d ⁇ spacing of the peaks identified in the experimental XRPD pattern of FIG. 42. The entire list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal.
  • the cocrystal may be characterized by at least two peaks selected from the peaks at 8.3, 11.2, and 15.8 °2 ⁇ ⁇ 0.2°2 ⁇ or their corresponding d ⁇ spacing as well as by an XRPD pattern substantially similar to FIG. 42.
  • Table 4 Crystalline form 1 of 5 ⁇ MeO ⁇ T fumarate Table 5: Crystalline form 1 of tryptammonium hydromalate Table 6: Crystalline form 1 of tryptammonium hydrophthalate Table 7: Crystalline form 1 of 4 ⁇ MeO ⁇ MiPT fumarate Table 8: Crystalline form 1 of 4 ⁇ HO ⁇ PiPT hydrofumarate Table 9: Crystalline form 1 of 5 ⁇ Cl ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ Cl ⁇ T Table 10: Crystalline form 1 of 5 ⁇ Cl ⁇ T hydromaleate Table 11: Crystalline form 1 of 5 ⁇ Cl ⁇ T hydrophthalate Table 12: Crystalline form 1 of 5 ⁇ Cl ⁇ T malate Table 13: Crystalline form 1 of 5 ⁇ MeO ⁇ T ⁇ N ⁇ Suc ⁇ 5 ⁇ MeO ⁇ T Table 14: Crystalline form 1 of 5 ⁇ Me ⁇ T Table 15: Crystalline form 1 of 4 ⁇ HO ⁇ MCPT fumarate Table 16: Crystalline form 1 of 4 ⁇ HO ⁇ DiPT hydrofumarate References Dolom

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Abstract

This disclosure relates to bis(2-(5-methoxy-1H-indol-3-yl)ethan-1-aminium) (2E)-but-2 enedioate (5-MeO-T fumarate), crystalline 5-MeO-T fumarate, 2-(1H-indol-3-yl)ethan-1-aminium 3- carboxy-2-hydroxypropanoate (tryptammonium hydromalate), crystalline tryptammonium hydromalate, 2-(1H-indol-3-yl)ethan-1-aminium 2-carboxybenzoate (tryptammonium hydrophthalate), crystalline tryptammonium hydrophthalate, bis([2-(4-methoxy-1H-indol-3- yl)ethyl](methyl)(propan-2-yl)azanium) (2E)-but-2-enedioate (4-MeO-MiPT fumarate), crystalline 4- MeO-MiPT fumarate, [2-(4-hydroxy-1H-indol-3-yl)ethyl](propan-2-yl)propylazanium (2E)-3 carboxyprop-2-enoate (4-HO-PiPT hydrofumarate), crystalline 4-HO-PiPT hydrofumarate, 2-(5- chloro-1H-indol-3-yl)ethan-1-aminium 2-{[2-(5-chloro-1H-indol-3-yl)ethyl]azaniumyl}butanedioate (5-CI-T-N-Suc-5-CI-T), crystalline 5-CI-T- N-Suc-5-CI-T, 2-(5-chloro-1H-indol-3-yl)ethan-1-aminium 3- carboxy-2-hydroxypropanoate (5-CI-T hydromaleate), crystalline 5-CI-T hydromaleate, 2-(5-chloro- 1H-indol-3-yl)ethan-1-aminium 2-carboxybenzoate (5-CI-T hydrophthalate), crystalline 5-CI-T hydrophthalate, bis(2-(5-chloro-1H-indol-3-yl)ethan-1-aminium) 2-hydroxybutanedioate (5-CI-T malate), crystalline 5-CI-T malate, 2-(5-methoxy-1H-indol-3-yl)ethan-1-aminium 2-{[2-(5-methoxy- 1H-indol-3-yl)ethyl]azaniumyl}butanedioate (5-MeO-T-N-Suc-5-MeO-T), crystalline 5-MeO-T- N-Suc-5-MeO-T, 2-(5-methyl-lH-indol-3-yl)ethan-l-amine (5-Me-T), crystalline 5-Me-T, bis(N-[2-(4-hydroxy- 1H-indol-3-yl)ethyl]-N-methylcyclopropanaminium) (2E)-but-2-enedioate (4-HO-MCPT fumarate), crystalline 4-HO-MCPT fumarate, [2-(4-hydroxy-1H-indol-3-yl)ethyl]bis(propan-2-yl)azanium (2 E)-3- carboxyprop-2-enoate (4-HO-DiPT hydrofumarate), crystalline 4-HO-DiPT hydrofumarate, and specific crystalline forms thereof, including crystalline form 1 of each of the previously recited compounds, to compositions containing the same, and to methods of treatment using them.

Description

  TRYPTAMINE DERIVATIVES  Cross‐Reference to Related Applications  [001] This application claims priority to U.S. Provisional Application No. 63/385,261, filed on  November 29, 2022; U.S. Provisional Application No. 63/385,287, filed on November 29, 2022; U.S.  Provisional Application No. 63/385,448, filed on November 30, 2022; U.S. Provisional Application No.  63/385,662, filed on December 1, 2022; U.S. Provisional Application No. 63/385,664, filed on  December 1, 2022; U.S. Provisional Application No. 63/385,665, filed on December 1, 2022; U.S.  Provisional Application No. 63/385,666, filed on December 1, 2022; U.S. Provisional Application No.  63/385,667, filed on December 1, 2022; U.S. Provisional Application No. 63/386,501, filed on  December 8, 2022; U.S. Provisional Application No. 63/386,523, filed on December 8, 2022; U.S.  Provisional Application No. 63/386,534, filed on December 8, 2022; U.S. Provisional Application No.  63/386,502, filed on December 8, 2022; and U.S. Provisional Application No. 63/386,503, filed on  December 8, 2022; the disclosures of which are each incorporated herein by reference.  Technical Field  [002] This disclosure relates to bis(2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐ enedioate (5‐methoxytryptammonium fumarate or 5‐MeO‐T fumarate), crystalline 5‐MeO‐T  fumarate, and specific crystalline forms thereof, including crystalline form 1 of 5‐MeO‐T fumarate; to  pharmaceutical compositions containing 5‐MeO‐T fumarate or crystalline 5‐MeO‐T fumarate,  including crystalline form 1 of 5‐MeO‐T fumarate; and to methods of treatment/therapeutic uses of  5‐MeO‐T fumarate or crystalline 5‐MeO‐T fumarate, including crystalline form 1 of 5‐MeO‐T  fumarate.  [003] This disclosure further relates to 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐ hydroxypropanoate (tryptammonium hydromalate), crystalline tryptammonium hydromalate, and  specific crystalline forms thereof, including crystalline form 1 of tryptammonium hydromalate; to  pharmaceutical compositions containing tryptammonium hydromalate or crystalline  tryptammonium hydromalate, including crystalline form 1 of tryptammonium hydromalate; and to  methods of treatment/therapeutic uses of tryptammonium hydromalate or crystalline  tryptammonium hydromalate, including crystalline form 1 of tryptammonium hydromalate.  [004] This disclosure further relates to 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate  (tryptammonium hydrophthalate), crystalline tryptammonium hydrophthalate, and specific  crystalline forms thereof, including crystalline form 1 of tryptammonium hydrophthalate; to  pharmaceutical compositions containing tryptammonium hydrophthalate or crystalline  tryptammonium hydrophthalate, including crystalline form 1 of tryptammonium hydrophthalate;    and to methods of treatment/therapeutic uses of tryptammonium hydrophthalate or crystalline  tryptammonium hydrophthalate, including crystalline form 1 of tryptammonium hydrophthalate.  [005] This disclosure further relates to bis([2‐(4‐methoxy‐1H‐indol‐3‐yl)ethyl](methyl)(propan‐2‐ yl)azanium) (2E)‐but‐2‐enedioate (4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate or 4‐ MeO‐MiPT fumarate), crystalline 4‐MeO‐MiPT fumarate, and specific crystalline forms thereof,  including crystalline form 1 of 4‐MeO‐MiPT fumarate; to pharmaceutical compositions containing 4‐ MeO‐MiPT fumarate or crystalline 4‐MeO‐MiPT fumarate, including crystalline form 1 of 4‐MeO‐ MiPT fumarate; and to methods of treatment/therapeutic uses of 4‐MeO‐MiPT fumarate or  crystalline 4‐MeO‐MiPT fumarate, including crystalline form 1 of 4‐MeO‐MiPT fumarate.  [006] This disclosure further relates to [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl](propan‐2‐ yl)propylazanium (2E)‐3‐carboxyprop‐2‐enoate (4‐hydroxy‐N‐propyl‐N‐isopropyltryptammnonium  hydrofumarate or 4‐HO‐PiPT hydrofumarate), crystalline 4‐HO‐PiPT hydrofumarate, and specific  crystalline forms thereof, including crystalline form 1 of 4‐HO‐PiPT hydrofumarate; to  pharmaceutical compositions containing 4‐HO‐PiPT hydrofumarate or crystalline 4‐HO‐PiPT  hydrofumarate, including crystalline form 1 of 4‐HO‐PiPT hydrofumarate; and to methods of  treatment/therapeutic uses of 4‐HO‐PiPT hydrofumarate or crystalline 4‐HO‐PiPT hydrofumarate,  including crystalline form 1 of 4‐HO‐PiPT hydrofumarate.  [007] This disclosure further relates to 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐chloro‐ 1H‐indol‐3‐yl)ethyl]azaniumyl}butanedioate (5‐chlorotryptammonium N‐succinyl‐5‐ chlorotryptammonium or 5‐Cl‐T∙N‐Suc‐5‐Cl‐T), crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, and specific crystalline  forms thereof, including crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T; to pharmaceutical compositions  containing 5‐Cl‐T∙N‐Suc‐5‐Cl‐T or crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, including crystalline form 1 of 5‐Cl‐ T∙N‐Suc‐5‐Cl‐T; and to methods of treatment/therapeutic uses of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T or crystalline 5‐ Cl‐T∙N‐Suc‐5‐Cl‐T, including crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T.  [008] This disclosure further relates to 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐ hydroxypropanoate (5‐chlorotryptammonium hydromaleate or 5‐Cl‐T hydromaleate), crystalline 5‐ Cl‐T hydromaleate, and specific crystalline forms thereof, including crystalline form 1 of 5‐Cl‐T  hydromaleate; to pharmaceutical compositions containing 5‐Cl‐T hydromaleate or crystalline 5‐Cl‐T  hydromaleate, including crystalline form 1 of 5‐Cl‐T hydromaleate; and to methods of  treatment/therapeutic uses of 5‐Cl‐T hydromaleate or crystalline 5‐Cl‐T hydromaleate, including  crystalline form 1 of 5‐Cl‐T hydromaleate.  [009] This disclosure further relates to 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐ carboxybenzoate (5‐chlorotryptammonium hydrophthalate or 5‐Cl‐T hydrophthalate), crystalline 5‐ Cl‐T hydrophthalate, and specific crystalline forms thereof, including crystalline form 1 of 5‐Cl‐T    hydrophthalate; to pharmaceutical compositions containing 5‐Cl‐T hydrophthalate or crystalline 5‐ Cl‐T hydrophthalate, including crystalline form 1 of 5‐Cl‐T hydrophthalate; and to methods of  treatment/therapeutic uses of 5‐Cl‐T hydrophthalate or crystalline 5‐Cl‐T hydrophthalate, including  crystalline form 1 of 5‐Cl‐T hydrophthalate.  [010] This disclosure further relates to bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium) 2‐ hydroxybutanedioate (5‐chlorotryptammonium malate or 5‐Cl‐T malate), crystalline 5‐Cl‐T malate,  and specific crystalline forms thereof, including crystalline form 1 of 5‐Cl‐T malate; to  pharmaceutical compositions containing 5‐Cl‐T malate or crystalline 5‐Cl‐T malate, including  crystalline form 1 of 5‐Cl‐T malate; and to methods of treatment/therapeutic uses of 5‐Cl‐T malate  or crystalline 5‐Cl‐T malate, including crystalline form 1 of 5‐Cl‐T malate.  [011] This disclosure further relates to 2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐ methoxy‐1H‐indol‐3‐yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium or 5‐MeO‐T∙N‐Suc‐5‐MeO‐T), crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, and  specific crystalline forms thereof, including crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T; to  pharmaceutical compositions containing 5‐MeO‐T∙N‐Suc‐5‐MeO‐T or crystalline 5‐MeO‐T∙N‐Suc‐5‐ MeO‐T, including crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T; and to methods of  treatment/therapeutic uses of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T or crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T,  including crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T.  [012] This disclosure further relates to 2‐(5‐methyl‐1H‐indol‐3‐yl)ethan‐1‐amine (5‐ methyltryptamine or 5‐Me‐T), crystalline 5‐Me‐T, and specific crystalline forms thereof, including  crystalline form 1 of 5‐Me‐T; to pharmaceutical compositions containing 5‐Me‐T or crystalline 5‐Me‐ T, including crystalline form 1 of 5‐Me‐T; and to methods of treatment/therapeutic uses of 5‐Me‐T  or crystalline 5‐Me‐T, including crystalline form 1 of 5‐Me‐T.  [013] This disclosure further relates to bis(N‐[2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]‐N‐ methylcyclopropanaminium) (2E)‐but‐2‐enedioate (4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate or 4‐HO‐MCPT fumarate), crystalline 4‐HO‐MCPT fumarate,  and specific crystalline forms thereof, including crystalline form 1 of 4‐HO‐MCPT fumarate; to  pharmaceutical compositions containing 4‐HO‐MCPT fumarate or crystalline 4‐HO‐MCPT fumarate,  including crystalline form 1 of 4‐HO‐MCPT fumarate; and to methods of treatment/therapeutic uses  of 4‐HO‐MCPT fumarate or crystalline 4‐HO‐MCPT fumarate, including crystalline form 1 of 4‐HO‐ MCPT fumarate.  [014] This disclosure further relates to [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]bis(propan‐2‐yl)azanium  (2E)‐3‐carboxyprop‐2‐enoate (4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate or 4‐HO‐ DiPT hydrofumarate), crystalline 4‐HO‐DiPT hydrofumarate, and specific crystalline forms thereof,    including crystalline form 1 of 4‐HO‐DiPT hydrofumarate; to pharmaceutical compositions containing  4‐HO‐DiPT hydrofumarate or crystalline 4‐HO‐DiPT hydrofumarate, including crystalline form 1 of 4‐ HO‐DiPT hydrofumarate; and to methods of treatment/therapeutic uses of 4‐HO‐DiPT  hydrofumarate or crystalline 4‐HO‐DiPT hydrofumarate, including crystalline form 1 of 4‐HO‐DiPT  hydrofumarate.  Background of the Invention  [015] Obtaining specific salts or crystalline forms of an active pharmaceutical ingredient (API) is  extremely useful in drug development. It permits better characterization of the drug candidate’s  chemical and physical properties. Crystalline forms often have better chemical and physical  properties than the API in its amorphous state. Such crystalline forms may possess more favorable  pharmaceutical and pharmacological properties or be easier to process. Additionally, preparing a  crystalline API and solving its crystal structure provides the gold standard for chemical  characterization and determining the molecular formula (and molecular weight) of the API.  Accordingly, preparing a crystalline form with an accompanying crystal structure thereof prevents  potential ambiguities and/or inaccuracies in the API’s molecular weight. This is important because  the API’s molecular weight is used to calculate the concentration of compositions comprising that  API. Thus, inaccuracies in molecular weight may lead to errors in the calculations pertaining to  dosing, potency, toxicity, etc. in all downstream in vitro and in vivo assays that correlated the  concentration of the API with a measured property. Accordingly, there remains a need to obtain and  characterize crystalline forms of APIs, such as tryptamines and other psychedelic drug compounds.   Summary of the Invention  [016] This disclosure relates to bis(2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐ enedioate (5‐methoxytryptammonium fumarate or 5‐MeO‐T fumarate), crystalline 5‐MeO‐T  fumarate, and specific crystalline forms thereof. In one embodiment, this disclosure pertains to  particular crystalline forms of 5‐MeO‐T fumarate, including crystalline form 1 of 5‐MeO‐T fumarate.  In one embodiment, crystalline form 1 of 5‐MeO‐T fumarate is characterized by at least one of: a  monoclinic, P21/c space group at a temperature of about 297(2) K; unit cell dimensions a = 5.8070(3)  Å, b = 24.2768(13) Å, c = 8.9334(5) Å, α = 90°, β = 103.360(2)°, and ɣ = 90°; an X‐ray powder  diffraction (XRPD) pattern substantially similar to FIG. 30; and an X‐ray powder diffraction pattern  characterized by at least two peaks selected from 7.3, 12.5, and 24.8 °2θ ± 0.2 °2θ.    [017] This disclosure further relates to 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐ hydroxypropanoate (tryptammonium hydromalate), crystalline tryptammonium hydromalate, and  specific crystalline forms thereof. In one embodiment, this disclosure pertains to particular  crystalline forms of tryptammonium hydromalate, including crystalline form 1 of tryptammonium    hydromalate. In one embodiment, crystalline form 1 of tryptammonium hydromalate is  characterized by at least one of: an orthorhombic, P212121 space group at a temperature of about  297(2) K; unit cell dimensions a = 7.2012(5) Å, b = 8.2509(5) Å, c = 24.7541(16) Å, α = 90°, β = 90°,  and ɣ = 90°; an X‐ray powder diffraction (XRPD) pattern substantially similar to FIG. 31; and an X‐ray  powder diffraction pattern characterized by at least two peaks selected from 7.1, 11.3, and 20.9 °2θ  ± 0.2 °2θ.    [018] This disclosure further relates to 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate  (tryptammonium hydrophthalate), crystalline tryptammonium hydrophthalate, and specific  crystalline forms thereof. In one embodiment, this disclosure pertains to particular crystalline forms  of tryptammonium hydrophthalate, including crystalline form 1 of tryptammonium hydrophthalate.  In one embodiment, crystalline form 1 of tryptammonium hydrophthalate is characterized by at  least one of: a monoclinic, C2/c space group at a temperature of about 297(2) K; unit cell dimensions  a = 18.7823(11) Å, b = 5.7731(3) Å, c = 29.3825(19) Å, α = 90°, β = 90.617(2)°, and ɣ = 90°; an X‐ray  powder diffraction (XRPD) pattern substantially similar to FIG. 32; and an X‐ray powder diffraction  pattern characterized by at least two peaks selected from 6.0, 11.2, and 15.4 °2θ ± 0.2 °2θ.    [019] This disclosure further relates to bis([2‐(4‐methoxy‐1H‐indol‐3‐yl)ethyl](methyl)(propan‐2‐ yl)azanium) (2E)‐but‐2‐enedioate (4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate or 4‐ MeO‐MiPT fumarate), crystalline 4‐MeO‐MiPT fumarate, and specific crystalline forms thereof. In  one embodiment, this disclosure pertains to particular crystalline forms of 4‐MeO‐MiPT fumarate,  including crystalline form 1 of 4‐MeO‐MiPT fumarate. In one embodiment, crystalline form 1 of 4‐ MeO‐MiPT fumarate is characterized by at least one of: a monoclinic, P21/n space group at a  temperature of about 297(2) K; unit cell dimensions a = 9.1438(3) Å, b = 13.8957(6) Å, c = 13.6658(6)  Å, α = 90°, β = 94.6140(10)°, and ɣ = 90°; an X‐ray powder diffraction (XRPD) pattern substantially  similar to FIG. 33; and an X‐ray powder diffraction pattern characterized by at least two peaks  selected from 9.1, 14.5, and 16.0 °2θ ± 0.2 °2θ.    [020] This disclosure further relates to [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl](propan‐2‐ yl)propylazanium (2E)‐3‐carboxyprop‐2‐enoate (4‐hydroxy‐N‐propyl‐N‐isopropyltryptammnonium  hydrofumarate or 4‐HO‐PiPT hydrofumarate), crystalline 4‐HO‐PiPT hydrofumarate, and specific  crystalline forms thereof. In one embodiment, this disclosure pertains to particular crystalline forms  of 4‐HO‐PiPT hydrofumarate, including crystalline form 1 of 4‐HO‐PiPT hydrofumarate. In one  embodiment, crystalline form 1 of 4‐HO‐PiPT hydrofumarate is characterized by at least one of: an  orthorhombic, P212121 space group at a temperature of about 297(2) K; unit cell dimensions a =  7.8854(7) Å, b = 12.7401(11) Å, c = 20.5577(18) Å, α = 90°, β = 90°, and ɣ = 90°; an X‐ray powder    diffraction (XRPD) pattern substantially similar to FIG. 34; and an X‐ray powder diffraction pattern  characterized by at least two peaks selected from 11.1, 12.0, and 15.8 °2θ ± 0.2 °2θ.    [021] This disclosure further relates to 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐chloro‐ 1H‐indol‐3‐yl)ethyl]azaniumyl}butanedioate (5‐chlorotryptammonium N‐succinyl‐5‐ chlorotryptammonium or 5‐Cl‐T∙N‐Suc‐5‐Cl‐T), crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, and specific crystalline  forms thereof. In one embodiment, this disclosure pertains to particular crystalline forms of 5‐Cl‐ T∙N‐Suc‐5‐Cl‐T, including crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T. In one embodiment, crystalline  form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T is characterized by at least one of: a triclinic, P1ത  space group at a  temperature of about 300(2) K; unit cell dimensions a = 9.5806(13) Å, b = 11.1666(14) Å, c =  11.5518(17) Å, α = 87.333(5)°, β = 74.347(5)°, and ɣ = 85.637(5)°; an X‐ray powder diffraction (XRPD)  pattern substantially similar to FIG. 35; and an X‐ray powder diffraction pattern characterized by at  least two peaks selected from 12.8, 15.9, and 22.9 °2θ ± 0.2 °2θ.    [022] This disclosure further relates to 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐ hydroxypropanoate (5‐chlorotryptammonium hydromaleate or 5‐Cl‐T hydromaleate), crystalline 5‐ Cl‐T hydromaleate, and specific crystalline forms thereof. In one embodiment, this disclosure  pertains to particular crystalline forms of 5‐Cl‐T hydromaleate, including crystalline form 1 of 5‐Cl‐T  hydromaleate. In one embodiment, crystalline form 1 of 5‐Cl‐T hydromaleate is characterized by at  least one of: a monoclinic, P21/c space group at a temperature of about 300(2) K; unit cell  dimensions a = 9.6320(7) Å, b = 5.4224(4) Å, c = 28.494(2) Å, α = 90°, β = 95.758(3)°, and ɣ = 90°; an  X‐ray powder diffraction (XRPD) pattern substantially similar to FIG. 36; and an X‐ray powder  diffraction pattern characterized by at least two peaks selected from 9.2, 10.6, and 14.8 °2θ ± 0.2  °2θ.    [023] This disclosure further relates to 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐ carboxybenzoate (5‐chlorotryptammonium hydrophthalate or 5‐Cl‐T hydrophthalate), crystalline 5‐ Cl‐T hydrophthalate, and specific crystalline forms thereof. In one embodiment, this disclosure  pertains to particular crystalline forms of 5‐Cl‐T hydrophthalate, including crystalline form 1 of 5‐Cl‐T  hydrophthalate. In one embodiment, crystalline form 1 of 5‐Cl‐T hydrophthalate is characterized by  at least one of: a triclinic, P1ത  space group at a temperature of about 300(2) K; unit cell dimensions a  = 7.4013(6) Å, b = 9.8217(9) Å, c = 12.1614(12) Å, α = 83.285(3)°, β = 79.601(3)°, and ɣ = 78.437(3)°;  an X‐ray powder diffraction (XRPD) pattern substantially similar to FIG. 37; and an X‐ray powder  diffraction pattern characterized by at least two peaks selected from 11.3, 12.3, and 15.4 °2θ ± 0.2  °2θ.    [024] This disclosure further relates to bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium) 2‐ hydroxybutanedioate (5‐chlorotryptammonium malate or 5‐Cl‐T malate), crystalline 5‐Cl‐T malate,    and specific crystalline forms thereof. In one embodiment, this disclosure pertains to particular  crystalline forms of 5‐Cl‐T malate, including crystalline form 1 of 5‐Cl‐T malate. In one embodiment,  crystalline form 1 of 5‐Cl‐T malate is characterized by at least one of: a monoclinic, P21 space group  at a temperature of about 300(2) K; unit cell dimensions a = 8.9975(8) Å, b = 12.3798(12) Å, c =  11.3628(11) Å, α = 90°, β = 106.617(3)°, and ɣ = 90°; an X‐ray powder diffraction (XRPD) pattern  substantially similar to FIG. 38; and an X‐ray powder diffraction pattern characterized by at least two  peaks selected from 12.5, 13.2, and 14.3 °2θ ± 0.2 °2θ.    [025] This disclosure further relates to 2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐ methoxy‐1H‐indol‐3‐yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium or 5‐MeO‐T∙N‐Suc‐5‐MeO‐T), crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, and  specific crystalline forms thereof. In one embodiment, this disclosure pertains to particular  crystalline forms of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, including crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐ T. In one embodiment, crystalline form 5‐MeO‐T∙N‐Suc‐5‐MeO‐T is characterized by at least one of: a  triclinic, P1ത space group at a temperature of about 300(2) K; unit cell dimensions a = 9.5838(10) Å, b  = 10.9915(12) Å, c = 12.6894(11) Å, α = 87.708(3)°, β = 71.246(3)°, and ɣ = 84.805(4)°; an X‐ray  powder diffraction (XRPD) pattern substantially similar to FIG. 39; and an X‐ray powder diffraction  pattern characterized by at least two peaks selected from 7.4, 18.4, and 19.6 °2θ ± 0.2 °2θ.    [026] This disclosure further relates to 2‐(5‐methyl‐1H‐indol‐3‐yl)ethan‐1‐amine (5‐ methyltryptamine or 5‐Me‐T), crystalline 5‐Me‐T, and specific crystalline forms thereof. In one  embodiment, this disclosure pertains to particular crystalline forms of 5‐Me‐T, including crystalline  form 1 of 5‐Me‐T. In one embodiment, crystalline form 1 of 5‐Me‐T is characterized by at least one  of: an orthorhombic, Pbca space group at a temperature of about 300(2) K; unit cell dimensions a =  9.1099(11) Å, b = 11.3907(11) Å, c = 19.154(2) Å, α = 90°, β = 90°, and ɣ = 90°; an X‐ray powder  diffraction (XRPD) pattern substantially similar to FIG. 40; and an X‐ray powder diffraction pattern  characterized by at least two peaks selected from 13.4, 15.5, and 19.5 °2θ ± 0.2 °2θ.    [027] This disclosure further relates to bis(N‐[2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]‐N‐ methylcyclopropanaminium) (2E)‐but‐2‐enedioate (4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate or 4‐HO‐MCPT fumarate), crystalline 4‐HO‐MCPT fumarate,  and specific crystalline forms thereof. In one embodiment, this disclosure pertains to particular  crystalline forms of 4‐HO‐MCPT fumarate, including crystalline form 1 of 4‐HO‐MCPT fumarate. In  one embodiment, crystalline form 1 of 4‐HO‐MCPT fumarate is characterized by at least one of: a  monoclinic, C2/c space group at a temperature of about 300(2) K; unit cell dimensions a =  19.5453(17) Å, b = 9.3265(7) Å, c = 17.4448(16) Å, α = 90°, β = 109.390(3)°, and ɣ = 90°; an X‐ray    powder diffraction (XRPD) pattern substantially similar to FIG. 41; and an X‐ray powder diffraction  pattern characterized by at least two peaks selected from 9.6, 10.7, and 16.6 °2θ ± 0.2 °2θ.    [028] This disclosure further relates to [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]bis(propan‐2‐yl)azanium  (2E)‐3‐carboxyprop‐2‐enoate (4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate or 4‐HO‐ DiPT hydrofumarate), crystalline 4‐HO‐DiPT hydrofumarate, and specific crystalline forms thereof. In  one embodiment, this disclosure pertains to particular crystalline forms of 4‐HO‐DiPT  hydrofumarate, including crystalline form 1 of 4‐HO‐DiPT hydrofumarate. In one embodiment,  crystalline form 1 of 4‐HO‐DiPT hydrofumarate is characterized by at least one of: an orthorhombic,  P212121 space group at a temperature of about 300(2) K; unit cell dimensions a = 7.9541(3) Å, b =  12.5763(5) Å, c = 20.3351(6) Å, α = 90°, β = 90°, and ɣ = 90°; an X‐ray powder diffraction (XRPD)  pattern substantially similar to FIG. 42; and an X‐ray powder diffraction pattern characterized by at  least two peaks selected from 8.3, 11.2, and 15.8 °2θ ± 0.2 °2θ.    [029] The disclosure further relates to a composition comprising 5‐MeO‐T fumarate, crystalline 5‐ MeO‐T fumarate, or specific crystalline forms thereof, such as crystalline form 1 of 5‐MeO‐T  fumarate, and at least one excipient.  [030] The disclosure further relates to a composition comprising tryptammonium hydromalate,  crystalline tryptammonium hydromalate, or specific crystalline forms thereof, such as crystalline  form 1 of tryptammonium hydromalate, and at least one excipient.  [031] The disclosure further relates to a composition comprising tryptammonium hydrophthalate,  crystalline tryptammonium hydrophthalate, or specific crystalline forms thereof, such as crystalline  form 1 of tryptammonium hydrophthalate, and at least one excipient.  [032] The disclosure further relates to a composition comprising 4‐MeO‐MiPT fumarate, crystalline  4‐MeO‐MiPT fumarate, or specific crystalline forms thereof, such as crystalline form 1 of 4‐MeO‐ MiPT fumarate, and at least one excipient.  [033] The disclosure further relates to a composition comprising 4‐HO‐PiPT hydrofumarate,  crystalline 4‐HO‐PiPT hydrofumarate, or specific crystalline forms thereof, such as crystalline form 1  of 4‐HO‐PiPT hydrofumarate, and at least one excipient.  [034] The disclosure further relates to a composition comprising 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐ Cl‐T∙N‐Suc‐5‐Cl‐T, or specific crystalline forms thereof, such as crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐ T, and at least one excipient.  [035] The disclosure further relates to a composition comprising 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, or specific crystalline forms thereof, such as crystalline form 1 of 5‐Cl‐T  hydromaleate, and at least one excipient.    [036] The disclosure further relates to a composition comprising 5‐Cl‐T hydrophthalate, crystalline  5‐Cl‐T hydrophthalate, or specific crystalline forms thereof, such as crystalline form 1 of 5‐Cl‐T  hydrophthalate, and at least one excipient.  [037] The disclosure further relates to a composition comprising 5‐Cl‐T malate, crystalline 5‐Cl‐T  malate, or specific crystalline forms thereof, such as crystalline form 1 of 5‐Cl‐T malate, and at least  one excipient.  [038] The disclosure further relates to a composition comprising 5‐MeO‐T∙N‐Suc‐5‐MeO‐T,  crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, or specific crystalline forms thereof, such as crystalline form 1  of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, and at least one excipient.  [039] The disclosure further relates to a composition comprising 5‐Me‐T, crystalline 5‐Me‐T, or  specific crystalline forms thereof, such as crystalline form 1 of 5‐Me‐T, and at least one excipient.  [040] The disclosure further relates to a composition comprising 4‐HO‐MCPT fumarate, crystalline  4‐HO‐MCPT fumarate, or specific crystalline forms thereof, such as crystalline form 1 of 4‐HO‐MCPT  fumarate, and at least one excipient.  [041] The disclosure further relates to a composition comprising 4‐HO‐DiPT hydrofumarate,  crystalline 4‐HO‐DiPT hydrofumarate, or specific crystalline forms thereof, such as crystalline form 1  of 4‐HO‐DiPT hydrofumarate, and at least one excipient.  [042] The disclosure also provides a composition comprising 5‐MeO‐T fumarate, crystalline 5‐ MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate,  tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐MiPT  fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate, or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate, as a first  component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic    drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone; and at least one excipient.  [043] The disclosure also relates to a method of preventing or treating a psychological disorder  comprising the step of administering to a subject in need thereof a therapeutically effective amount  of  5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate, or a composition according to this disclosure.  [044] The disclosure further relates to a method of preventing or treating inflammation and/or  pain, preventing or treating a neurological disorder, modulating activity of a mitogen‐activated  protein kinase (MAPK), modulating neurogenesis, or modulating neurite outgrowth comprising the  step of administering to a subject in need thereof a therapeutically effective amount of a compound  of  5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐   Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate, and to administering a pharmaceutical composition or a composition according to  the invention.  [045] As used herein, the term “a subject in need thereof” refers to a person requiring a  composition to treat a particular disease or condition (e.g., inflammation, pain, a psychological  disorder, modulating activity at a receptor, etc.). In one embodiment, the “subject in need thereof”  may be identified by analyzing, diagnosing, and/or determining whether the person (or subject)  requires the composition for treatment of a particular disease or condition. In one embodiment,  identifying a person in need of treatment comprises diagnosing a person with a medical condition,  e.g., a neurological disorder, a chemical imbalance, a hereditary condition, etc. In one embodiment,  identifying a person in need of treatment comprises performing a psychiatric evaluation. In one  embodiment, identifying a person in need of treatment comprises performing a blood test. In one  embodiment, identifying a person in need of treatment comprises determining whether a person  has a compulsive disorder. In one embodiment, identifying a person in need of treatment comprises  self‐identifying as having a compulsive disorder.  Description of the Figures  [046] FIG. 1 shows the molecular structure of crystalline form 1 of 5‐methoxytryptammonium  fumarate.  [047] FIG. 2 shows the molecular structure of crystalline form 1 of tryptammonium hydromalate.  [048] FIG. 3 shows the molecular structure of crystalline form 1 of tryptammonium  hydrophthalate.  [049] FIG. 4 shows the molecular structure of crystalline form 1 of 4‐methoxy‐N‐methyl‐N‐ isopropyltryptammonium fumarate.  [050] FIG. 5 shows the molecular structure of crystalline form 1 of 4‐hydroxy‐N‐propyl‐N‐ isopropyltryptammnonium hydrofumarate.  [051] FIG. 6 shows the molecular structure of crystalline form 1 of 5‐chlorotryptammonium N‐ succinyl‐5‐chlorotryptammonium.  [052] FIG. 7 shows the molecular structure of crystalline form 1 of 5‐chlorotryptammonium  hydromaleate.  [053] FIG. 8 shows the molecular structure of crystalline form 1 of 5‐chlorotryptammonium  hydrophthalate.    [054] FIG. 9 shows the molecular structure of crystalline form 1 of 5‐chlorotryptammonium  malate.  [055] FIG. 10 shows the molecular structure of crystalline form 1 of 5‐methoxytryptammonium N‐ succinyl‐5‐methoxytryptammonium.  [056] FIG. 11 shows the molecular structure of crystalline form 1 of 5‐methyltryptamine.  [057] FIG. 12 shows the molecular structure of crystalline form 1 of 4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate.  [058] FIG. 13 shows the molecular structure of crystalline form 1 of 4‐hydroxy‐N,N‐ diisopropyltryptammonium hydrofumarate.  [059] FIG. 14 shows the unit cell of crystalline form 1 of 5‐methoxytryptammonium fumarate  along the a‐axis.  [060] FIG. 15 shows the unit cell of crystalline form 1 of tryptammonium hydromalate along the a‐ axis.  [061] FIG. 16 shows the unit cell of crystalline form 1 of tryptammonium hydrophthalate along the  b‐axis.  [062] FIG. 17 shows the unit cell of crystalline form 1 of 4‐methoxy‐N‐methyl‐N‐ isopropyltryptammonium fumarate along the c‐axis.  [063] FIG. 18 shows the unit cell of crystalline form 1 of 4‐hydroxy‐N‐propyl‐N‐ isopropyltryptammnonium hydrofumarate along the a‐axis.  [064] FIG. 19 shows the unit cell of crystalline form 1 of 5‐chlorotryptammonium N‐succinyl‐5‐ chlorotryptammonium along the a‐axis.  [065] FIG. 20 shows the unit cell of crystalline form 1 of 5‐chlorotryptammonium hydromaleate  along the b‐axis.  [066] FIG. 21 shows the unit cell of crystalline form 1 of 5‐chlorotryptammonium hydrophthalate  along the c‐axis.  [067] FIG. 22 shows the unit cell of crystalline form 1 of 5‐chlorotryptammonium malate along the  a‐axis.  [068] FIG. 23 shows the unit cell of crystalline form 1 of 5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium along the a‐axis.  [069] FIG. 24 shows the unit cell of crystalline form 1 of 5‐methyltryptamine along the a‐axis.  [070] FIG. 25 shows the unit cell of crystalline form 1 of 4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate along the b‐axis.  [071] FIG. 26 shows the unit cell of crystalline form 1 of 4‐hydroxy‐N,N‐diisopropyltryptammonium  hydrofumarate along the a‐axis.    [072] FIG. 27 shows the 2:1 ratio of crystalline form 1 of 5‐methoxytryptammonium fumarate as a  dimer.  [073] FIG. 28 shows the 2:1 ratio of crystalline form 1 of 4‐methoxy‐N‐methyl‐N‐ isopropyltryptammonium fumarate as a dimer.  [074] FIG. 29 shows the 2:1 ratio of crystalline form 1 of 4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate as a dimer.  [075] FIG. 30 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐methoxytryptammonium fumarate.  [076] FIG. 31 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  tryptammonium hydromalate.  [077] FIG. 32 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  tryptammonium hydrophthalate.  [078] FIG. 33 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate.  [079] FIG. 34 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  4‐hydroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate.  [080] FIG. 35 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium.  [081] FIG. 36 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐chlorotryptammonium hydromaleate.  [082] FIG. 37 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐chlorotryptammonium hydrophthalate.  [083] FIG. 38 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐chlorotryptammonium malate.  [084] FIG. 39 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium.  [085] FIG. 40 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐methyltryptamine.  [086] FIG. 41 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  4‐hydroxy‐N‐methyl‐N‐cyclopropypltrytammonium fumarate.  [087] FIG. 42 shows the simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate.  Detailed Description   [088] Compounds     [089] This disclosure relates to bis(2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐ enedioate (5‐methoxytryptammonium fumarate or 5‐MeO‐T fumarate), crystalline 5‐MeO‐T  fumarate, 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate (tryptammonium  hydromalate), crystalline tryptammonium hydromalate, 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐ carboxybenzoate (tryptammonium hydrophthalate), crystalline tryptammonium hydrophthalate,  bis([2‐(4‐methoxy‐1H‐indol‐3‐yl)ethyl](methyl)(propan‐2‐yl)azanium) (2E)‐but‐2‐enedioate (4‐ methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate or 4‐MeO‐MiPT fumarate), crystalline 4‐ MeO‐MiPT fumarate, [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl](propan‐2‐yl)propylazanium (2E)‐3‐ carboxyprop‐2‐enoate (4‐hydroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate or 4‐HO‐ PiPT hydrofumarate), crystalline 4‐HO‐PiPT hydrofumarate, 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐ aminium 2‐{[2‐(5‐chloro‐1H‐indol‐3‐yl)ethyl]azaniumyl}butanedioate (5‐chlorotryptammonium N‐ succinyl‐5‐chlorotryptammonium or 5‐Cl‐T∙N‐Suc‐5‐Cl‐T), crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 2‐(5‐chloro‐ 1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate (5‐chlorotryptammonium  hydromaleate or 5‐Cl‐T hydromaleate), crystalline 5‐Cl‐T hydromaleate, 2‐(5‐chloro‐1H‐indol‐3‐ yl)ethan‐1‐aminium 2‐carboxybenzoate (5‐chlorotryptammonium hydrophthalate or 5‐Cl‐T  hydrophthalate), crystalline 5‐Cl‐T hydrophthalate, bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium)  2‐hydroxybutanedioate (5‐chlorotryptammonium malate or 5‐Cl‐T malate), crystalline 5‐Cl‐T malate,  2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐methoxy‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium  or 5‐MeO‐T∙N‐Suc‐5‐MeO‐T), crystalline or 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 2‐(5‐methyl‐1H‐indol‐3‐ yl)ethan‐1‐amine (5‐methyltryptamine or 5‐Me‐T), crystalline 5‐Me‐T, bis(N‐[2‐(4‐hydroxy‐1H‐indol‐ 3‐yl)ethyl]‐N‐methylcyclopropanaminium) (2E)‐but‐2‐enedioate (4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate or 4‐HO‐MCPT fumarate), crystalline 4‐HO‐MCPT fumarate, [2‐ (4‐hydroxy‐1H‐indol‐3‐yl)ethyl]bis(propan‐2‐yl)azanium (2E)‐3‐carboxyprop‐2‐enoate (4‐hydroxy‐ N,N‐diisopropyltryptammonium hydrofumarate or 4‐HO‐DiPT hydrofumarate), crystalline 4‐HO‐DiPT  hydrofumarate, and specific crystalline forms thereof, including crystalline form 1 of 5‐MeO‐T  fumarate, crystalline form 1 of tryptammonium hydromalate, crystalline form 1 of tryptammonium  hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT  hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate,  crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of  5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate,  and crystalline form 1 of 4‐HO‐DiPT hydrofumarate; to pharmaceutical compositions containing 5‐ MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium    hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate according to the disclosure. The therapeutic uses of 5‐MeO‐T fumarate, crystalline 5‐ MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate,  tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐MiPT  fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate according to the  disclosure are described below as well as compositions containing them. 5‐MeO‐T fumarate,  crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,    crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate, and some  exemplary methods used to characterize them are described below.   [090] 5‐MeO‐T fumarate has the following chemical formula: 
Figure imgf000018_0001
  [091] Tryptammonium hydromalate has the following chemical formula: 
Figure imgf000018_0002
  [092] Tryptammonium hydrophthalate has the following chemical formula: 
Figure imgf000018_0003
  [093] 4‐MeO‐MiPT fumarate has the following chemical formula:   
Figure imgf000019_0001
  [094] 4‐HO‐PiPT hydrofumarate has the following chemical formula: 
Figure imgf000019_0002
  [095] 5‐Cl‐T∙N‐Suc‐5‐Cl‐T has the following chemical formula: 
Figure imgf000019_0003
  [096] 5‐Cl‐T hydromaleate has the following chemical formula: 
Figure imgf000019_0004
  [097] 5‐Cl‐T hydrophthalate has the following chemical formula:   
Figure imgf000020_0001
  [098] 5‐Cl‐T malate has the following chemical formula: 
Figure imgf000020_0002
  [099] 5‐MeO‐T∙N‐Suc‐5‐MeO‐T has the following chemical formula: 
Figure imgf000020_0003
  [100] 5‐Me‐T has the following chemical formula: 
Figure imgf000020_0004
  [101] 4‐HO‐MCPT fumarate has the following chemical formula:   
Figure imgf000021_0001
  [102] 4‐HO‐DiPT hydrofumarate has the following chemical formula: 
Figure imgf000021_0002
  [103] Methods of Treatment and Therapeutic Uses  [104] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate according to the disclosure, and the methods and the compositions (e.g.,  pharmaceutical compositions) are used to regulate the activity of a neurotransmitter receptor by  administering a therapeutically effective dose of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate,  tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium  hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐ MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐   5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T  hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐ T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT  fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT  hydrofumarate or specific crystalline forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate,  crystalline form 1 of tryptammonium hydromalate, crystalline form 1 of tryptammonium  hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT  hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate,  crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of  5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate,  and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the disclosure. In one embodiment, 5‐MeO‐T  fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate according to the  disclosure, and the methods and the compositions (e.g., pharmaceutical compositions) are used to  treat inflammation and/or pain by administering a therapeutically effective dose of 5‐MeO‐T  fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT    hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the  disclosure.  [105] Methods of the disclosure also relate to the administration of a therapeutically effective  amount of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate,  crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate to prevent or treat a disease or condition, such as those discussed below for a  subject in need of treatment. 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium  hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐   MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate may be administered neat or as a composition comprising 5‐MeO‐T fumarate,  crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate as discussed  below.  [106] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT    hydrofumarate of the disclosure may be used to prevent and/or treat a psychological disorder. The  disclosure provides a method for preventing and/or treating a psychological disorder by  administering to a subject in need thereof a therapeutically effective amount of 5‐MeO‐T fumarate,  crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the  disclosure, including the exemplary embodiments discussed herein. The psychological disorder may  be chosen from: depression; psychotic disorder; schizophrenia; schizophreniform disorder (acute  schizophrenic episode); schizoaffective disorder; bipolar I disorder (mania, manic disorder, manic‐ depressive psychosis); bipolar II disorder; major depressive disorder; major depressive disorder with  psychotic feature (psychotic depression); delusional disorders (paranoia); shared psychotic disorder  (shared paranoia disorder); brief psychotic disorder (other and unspecified reactive psychosis);  psychotic disorder not otherwise specified (unspecified psychosis); paranoid personality disorder;  schizoid personality disorder; schizotypal personality disorder; anxiety disorder; social anxiety  disorder; substance‐induced anxiety disorder; selective mutism; panic disorder; panic attacks;  agoraphobia; attention deficit syndrome; post‐traumatic stress disorder (PTSD); premenstrual  dysphoric disorder (PMDD); and premenstrual syndrome (PMS).   [107] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐   MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used to prevent and/or treat a brain disorder. The  disclosure provides a method for preventing and/or treating a brain disorder (e.g., Huntington's  disease, Alzheimer's disease, dementia, and Parkinson's disease) by administering to a subject in  need thereof a therapeutically effective amount of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T  fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium  hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐ MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐ 5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T  hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐ T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT  fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT  hydrofumarate or specific crystalline forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate,  crystalline form 1 of tryptammonium hydromalate, crystalline form 1 of tryptammonium  hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT  hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate,  crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of  5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate,  and crystalline form 1 of 4‐HO‐DiPT hydrofumarate.   [108] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline    forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used to prevent and/or treat developmental disorders,  delirium, dementia, amnestic disorders and other cognitive disorders, psychiatric disorders due to a  somatic condition, drug‐related disorders, schizophrenia and other psychotic disorders, mood  disorders, anxiety disorders, somatoform disorders, factitious disorders, dissociative disorders,  eating disorders, sleep disorders, impulse control disorders, adjustment disorders, or personality  disorders. The disclosure provides a method for preventing and/or treating these disorders by  administering to a subject in need thereof a therapeutically effective amount of 5‐MeO‐T fumarate,  crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate including the  exemplary embodiments discussed above.  [109] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐   MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used to prevent and/or treat inflammation and/or pain,  such as for example inflammation and/or pain associated with inflammatory skeletal or muscular  diseases or conditions. The disclosure provides a method for preventing and/or treating an  inflammation and/or pain by administering to a subject in need thereof a therapeutically effective  amount of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate,  crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure, including the exemplary embodiments discussed herein. Generally  speaking, treatable “pain” includes nociceptive, neuropathic, and mix‐type. A method of the  disclosure may reduce or alleviate the symptoms associated with inflammation, including but not  limited to treating localized manifestation of inflammation characterized by acute or chronic  swelling, pain, redness, increased temperature, or loss of function in some cases. A method of the  disclosure may reduce or alleviate the symptoms of pain regardless of the cause of the pain,  including but not limited to reducing pain of varying severity, i.e., mild, moderate and severe pain,  acute pain and chronic pain. A method of the disclosure is effective in treating joint pain, muscle    pain, tendon pain, burn pain, and pain caused by inflammation such as rheumatoid arthritis. Skeletal  or muscular diseases or conditions which may be treated include but are not limited to  musculoskeletal sprains, musculoskeletal strains, tendinopathy, peripheral radiculopathy,  osteoarthritis, joint degenerative disease, polymyalgia rheumatica, juvenile arthritis, gout,  ankylosing spondylitis, psoriatic arthritis, systemic lupus erythematosus, costochondritis, tendonitis,  bursitis, such as the common lateral epicondylitis (tennis elbow), medial epicondylitis (pitchers  elbow) and trochanteric bursitis, temporomandibular joint syndrome, and fibromyalgia.  [110] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used to modulate activity of a mitogen‐activated protein  kinase (MAPK), comprising administering a composition of the invention. MAPKs provide a wide‐ ranging signaling cascade that allow cells to quickly respond to biotic and abiotic stimuli. Exemplary  MAPKs include, but are not limited to, Tropomyosin Receptor Kinase A (TrkA), P38‐alpha, and c‐Jun  N‐Terminal Kinase 3 (JNK3). TrkA is a high affinity catalytic receptor of nerve growth factor (NGF)  protein. TrkA regulates NGF response, influencing neuronal differentiation and outgrowth as well as  programmed cell death. p38‐alpha is involved with the regulation of pro‐inflammatory cytokines,  including TNF‐a. In the central nervous system, p38‐alpha regulates neuronal death and neurite  degeneration, and it is a common target of Alzheimer's disease therapies. JNK3 is a neuronal‐specific  protein isoform of the JNKs. It is involved with the regulation of apoptosis. JNK3 also plays a role in  modulating the response of cytokines, growth factors, and oxidative stress.  [111] As used herein, the term “modulating activity of a mitogen‐activated protein kinase” refers  to changing, manipulating, and/or adjusting the activity of a mitogen‐activated protein kinase. In one    embodiment, modulating the activity of a MAPK can influence neural health, neurogenesis, neural  growth and differentiation, and neurodegenerative diseases.   [112] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used to modulate neurogenesis, comprising administering a  composition of the invention. As used herein, the term “modulating neurogenesis” refers to  changing, manipulating, and/or adjusting the growth and development of neural tissue. In one  embodiment, neurogenesis comprises adult neurogenesis, in which new neural stem cells are  generated from neural stem cells in an adult animal. In one embodiment, modulating neurogenesis  comprises increasing and/or enhancing the rate at which new neural tissue is developed.  [113] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,    crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used to modulate neurite outgrowth, comprising  administering a composition of the invention. As used herein, the term “modulating neurite  outgrowth” refers to changing, manipulating, and/or adjusting the growth and development of  neural projections, or “neurites.” In one embodiment, neurogenesis comprises modulating the  growth of new neurites, the number of neurites per neuron, and/or neurite length. In one  embodiment, modulating neurite outgrowth comprises increasing and/or enhancing the rate and/or  length at which neurites develop.  [114] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used to prevent and/or treat sexual health disorders  including, but not limited to, hypoactive sexual desire disorder, hyperactive sexual desire disorder,  orgasmic disorder, arousal disorder, vaginismus, and dyspareunia. In some embodiments, the  disorder is a male sexual dysfunction disorder. In some embodiments, the disorder is a female sexual  dysfunction disorder.  [115] 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐   MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used to prevent and/or treat women’s health disorders  including, but not limited to, menstrual cramping, dysmenorrhea, post‐hysterectomy pain, vaginal or  vulvar vestibule mucosa disorder, menopausal‐related disorders, vaginal atrophy, or vulvar  vestibulitis.  [116] Compositions  [117] The disclosure also relates to compositions comprising an effective amount of 5‐MeO‐T  fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate and an excipient  (e.g., a pharmaceutically‐acceptable excipient). In another embodiment, the disclosure also relates  to pharmaceutical compositions comprising a therapeutically effective amount of 5‐MeO‐T  fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline    5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate and a  pharmaceutically acceptable excipient (also known as a pharmaceutically acceptable carrier). As  discussed above, 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate,  crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be, for example, therapeutically useful to prevent and/or treat  the psychological disorders, brain disorders, pain, and inflammation as well as the other disorders  described herein.   [118] A composition or a pharmaceutical composition of the disclosure may be in any form which  contains 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T    hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate. The composition may be, for example, a tablet, capsule, liquid suspension,  injectable, topical, or transdermal. The compositions generally contain, for example, about 1% to  about 99% by weight of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium  hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure and, for example, 99% to 1% by weight of at least one suitable  pharmaceutically acceptable excipient. In one embodiment, the composition may be between about  5% and about 75% by weight of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium  hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT    fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure, with the rest being at least one suitable pharmaceutically  acceptable excipient or at least one other adjuvant, as discussed below.  [119] Published US applications US 2018/0221396 A1 and US 2019/0142851 A1 disclose  compositions comprising a combination of a first purified psilocybin derivative with a second purified  psilocybin derivative, with one or two purified cannabinoids or with a purified terpene. Various  ratios of these components in the composition are also disclosed. The disclosures of US  2018/0221396 A1 and US 2019/0142851 A1 are incorporated herein by reference. According to this  disclosure, 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate,  crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used as the “first purified psilocybin derivative” in the  compositions described in US 2018/0221396 A1 and US 2019/0142851 A1. Accordingly, this  disclosure provides a composition comprising: a first component comprising 5‐MeO‐T fumarate,  crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT    hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the  disclosure; at least one second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, and (d) a purified terpene; and at least one  pharmaceutically‐acceptable excipient or at least one other adjuvant. Such a composition may be a  pharmaceutical composition wherein the components are present individually in therapeutically  effective amounts or by combination in a therapeutically effective amount to treat a disease,  disorder, or condition as described herein.   [120] When used in such compositions as a first component comprising 5‐MeO‐T fumarate,  crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the disclosure  with a second component selected from at least one of (a) a serotonergic drug, (b) a purified  psilocybin derivative, (c) a purified cannabinoid, and (d) a purified terpene, the compositions    represent particular embodiments of the invention. Compositions having as a first component 5‐ MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure with a second component selected from at least one of (e) an  adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine,  and (i) a purified hericenone represent additional particular embodiments of the invention  represented by the compositions having 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate,  tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium  hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐ MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐ 5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T  hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐ T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT  fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT  hydrofumarate or specific crystalline forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate,  crystalline form 1 of tryptammonium hydromalate, crystalline form 1 of tryptammonium  hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT  hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate,  crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of  5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate,  and crystalline form 1 of 4‐HO‐DiPT hydrofumarate according to the disclosure. In some  embodiments, the first and second components can be administered at the same time (e.g.,    together in the same composition), or at separate times over the course of treating a patient in need  thereof. Such a composition may be a pharmaceutical composition wherein the components are  present individually in therapeutically effective amounts or by combination in a therapeutically  effective amount to treat a disease, disorder, or condition as described herein.  [121] Within the context of this disclosure, the term “purified” means separated from other  materials, such as plant or fungal material, e.g., protein, chitin, cellulose, or water. In one  embodiment, the term “purified” refers to a compound substantially free of other materials. In one  embodiment, the term “purified” refers to a compound that is substantially free from a second  tryptamine compound. In one embodiment, the term “purified” refers to a compound substantially  free from histidine. In one embodiment, the term “purified” refers to a compound substantially free  from a biological material, such as mold, fungus, plant matter, or bacteria. In one embodiment, the  term “purified” refers to a compound substantially free from a paralytic.  [122] In one embodiment, the term “purified” refers to a compound which has been separated  from other compounds that are typically co‐extracted when the purified compound is extracted  from a naturally occurring organism. In one embodiment, a “purified” psilocybin derivative is  partially or completely isolated from other psilocybin derivatives present in a source material, such  as a psilocybin‐containing mushroom. In one example, “purified” baeocystin is substantially free  from psilocybin and/or psilocin. By contrast, traditional psilocybin mushroom extracts (aka crude  extracts or fruit body extracts) would be expected to contain an unpredictable and varying amount  of psilocybin, psilocin, baeocystin, norbaeocystin, salts thereof, or combinations thereof. Other  examples of unpurified psilocybin derivatives would include mycelium containing psilocybin  derivatives and/or naturally occurring fungal material such as biological material and/or structural  material such as chitin. Similarly, the term “cannabis extracts'' or “cannabinoid extracts” traditionally  refers to whole plants (aka crude or full spectrum extracts) which have not been subjected to further  purification to eliminate unwanted molecules that naturally occur in the cannabis plant. For  example, a “cannabis extract comprising cannabidiol” could be expected to include cannabidiol (aka  “CBD”) and also varying amounts of other compounds, including cannabinoids, terpenes, and other  biological material.  [123] In one embodiment, the term “purified” refers to a compound or composition that has been  crystallized.  [124] In one embodiment, the term “purified” refers to a compound or composition that has been  chromatographed, for example by gas chromatography, liquid chromatography (e.g., LC, HPLC, etc.),  etc.    [125] In one embodiment, the term “purified” refers to a compound or composition that has been  distilled.  [126] In one embodiment, the term “purified” refers to a compound or composition that has been  sublimed.  [127] In one embodiment, the term “purified” refers to a compound or composition that has been  subject to two or more steps chosen from crystallization, chromatography, distillation, or  sublimation.  [128] In one embodiment, the term “purified” refers to a compound that is between 80‐100%  pure.  [129] In one embodiment, the term “purified” refers to a compound that is between 90‐100%  pure.  [130] In one embodiment, the term “purified” refers to a compound that is between 95‐100%  pure.  [131] In one embodiment, the term “purified” refers to a compound that is between 99‐100%  pure.  [132] In one embodiment, the term “purified” refers to a compound that is between 99.9‐100%  pure.  [133] A serotonergic drug refers to a compound that binds to, blocks, or otherwise influences (e.g.,  via an allosteric reaction) activity at a serotonin receptor as described in paragraphs [0245]‐[0253] of  US 2018/0221396 A1 and [0305]‐[0311] US 2019/0142851 A1 as well as the disclosed exemplary  embodiments. Exemplary psilocybin derivatives include but are not limited to psilocybin itself and  the psilocybin derivatives described in paragraphs [0081]‐[0109] of US 2018/0221396 A1 and [0082]‐ [0110] US 2019/0142851 A1 as well as the disclosed exemplary embodiments. Exemplary  cannabinoids include but are not limited to the cannabinoids described in paragraphs [0111]‐[0145]  of US 2018/0221396 A1 and [0112]‐[0146] US 2019/0142851 A1 as well as the disclosed exemplary  embodiments. Exemplary terpenes include but are not limited to the terpenes described in  paragraphs [0160]‐[0238] of US 2018/0221396 A1 and [0161]‐[0300] US 2019/0142851 A1 as well as  the disclosed exemplary embodiments.   [134] A pharmaceutical formulation of the disclosure may comprise, consist essentially of, or  consist of (a) 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate,  crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐   Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure and (b) at least one second active compound selected from a  serotonergic drug, a purified psilocybin derivative, a purified cannabinoid, a purified terpene, an  adrenergic drug, a dopaminergic drug, a monoamine oxidase inhibitor, a purified erinacine, and a  purified hericenone, and (c) a pharmaceutically acceptable excipient. In some embodiments, 5‐MeO‐ T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate and the second active compound(s) are each present in a therapeutically effective  amount using purposefully engineered and unnaturally occurring molar ratios. Exemplary molar  ratios of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T    hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure to the second active compound in a composition of the disclosure  include but are not limited to from about 0.1:100 to about 100:0.1, from about 1:100 to about  100:1, from about 1:50 to about 50:1, from about 1:25 to about 25:1, from about 1:20 to about 20:1,  from about 1:10 to about 10:1, from about 1:5 to about 5:1, from about 1:2 to about 2:1 or may be  about 1:1.  [135] A pharmaceutical formulation of the disclosure may comprise a composition containing 5‐ MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure and a serotonergic drug, a purified psilocybin derivative, a purified  cannabinoid, or a purified terpene, each present in a therapeutically effective amount using  purposefully engineered and unnaturally occurring molar ratios. Published US applications US  2018/0221396 A1 and US 2019/0142851 A1 disclose compositions comprising a combination of a  purified psilocybin derivative with a second purified psilocybin derivative, with one or two purified    cannabinoids or with a purified terpene. According to this disclosure composition containing 5‐MeO‐ T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be used in place of a “purified psilocybin derivative” in the  compositions described in US 2018/0221396 A1 and US 2019/0142851 A1. Accordingly, the  disclosure provides a pharmaceutical formulation comprising as (a) 5‐MeO‐T fumarate, crystalline 5‐ MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate,  tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐MiPT  fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the disclosure  and at least one second component selected from (a) a purified psilocybin derivative, (b) a purified  cannabinoid, and (c) a purified terpene; and at least one pharmaceutically‐acceptable excipient or at    least one other adjuvant, as described herein. Such a composition may be a pharmaceutical  composition wherein the components are present individually in therapeutically effective amounts  or by combination in a therapeutically effective amount to treat a disease, disorder, or condition as  described herein.  [136] A serotonergic drug refers to a compound that binds to, blocks, or otherwise influences (e.g.,  via an allosteric reaction) activity at a serotonin receptor as described in paragraphs [0245]‐[0253] of  US 2018/0221396 A1 and [0305]‐[0311] US 2019/0142851 A1 as well as the disclosed exemplary  embodiments. Some exemplary serotonergic drugs include SSRIs and SNRIs. Some examples of  specific serotonergic drugs include the following molecules, including any salts, solvates, or  polymorphs thereof: 6‐allyl‐N,N‐diethyl‐NL; N,N‐dibutyl‐T; N,N‐diethyl‐T; N,N‐diisopropyl‐T; 5‐ methyoxy‐alpha‐methyl‐T; N,N‐dimethyl‐T; 2,alpha‐dimethyl‐T; alpha,N‐dimethyl‐T; N,N‐dipropyl‐T;  N‐ethyl‐N‐isopropyl‐T; alpha‐ethyl‐T; 6‐N,N‐Triethyl‐NL; 3,4‐dihydro‐7‐methoxy‐1‐methyl‐C; 7‐ methyoxy‐1‐methyl‐C; N,N‐dibutyl‐4‐hydroxy‐T; N,N‐diethyl‐4‐hydroxy‐T; N,N‐diisopropyl‐4‐hydroxy‐ T; N,N‐dimethyl‐4‐hydroxy‐T; N,N‐dimethyl‐5‐hydroxy‐T; N, N‐dipropyl‐4‐hydroxy‐T; N‐ethyl‐4‐ hydroxy‐N‐methyl‐T; 4‐hydroxy‐N‐isopropyl‐N‐methyl‐T; 4‐hydroxy‐N‐methyl‐N‐propyl‐T; 4‐hydroxy‐ N,N‐tetramethylene‐T; ibogaine; N,N‐diethyl‐L; N‐butyl‐N‐methyl‐T; N,N‐diisopropyl‐4,5‐ methylenedioxy‐T; N,N‐diisopropyl‐5,6‐methylenedioxy‐T; N,N‐dimethyl‐4,5‐methylenedioxy‐T; N,N‐ dimethyl‐5,6‐methylenedioxy‐T; N‐isopropyl‐N‐methyl‐5,6‐methylenedioxy‐T; N,N‐diethyl‐2‐methyl‐ T; 2‐N,N‐trimethyl‐T; N‐acetyl‐5‐methoxy‐T; N,N‐diethyl‐5‐methoxy‐T; N,N‐diisopropyl‐5‐methoxy‐T;  5‐methoxy‐N,N‐dimethyl‐T; N‐isopropyl‐4‐methoxy‐N‐methyl‐T; N‐isopropyl‐5‐methoxy‐N‐methyl‐T;  5,6‐dimethoxy‐N‐isopropyl‐N‐methyl‐T; 5‐methoxy‐N‐methyl‐T; 5‐methoxy‐N,N‐tetramethylene‐T;  6‐methoxy‐1‐methyl‐1,2,3,4‐tetrahydro‐C; 5‐methoxy‐2‐N,N‐trimethyl‐T; N,N‐dimethyl‐5‐ methylthio‐T; N‐isopropyl‐N‐methyl‐T; alpha‐methyl‐T; N‐ethyl‐T; N‐methyl‐T; 6‐propyl‐N L; N,N‐ tetramethylene‐T; tryptamine; 7‐methoxy‐1‐methyl‐1,2,3,4‐tetrahydro‐C; and alpha,N‐dimethyl‐5‐ methoxy‐T. For additional information regarding these compounds see Shulgin, A. T., & Shulgin, A.  (2016). Tihkal: The Continuation. Berkeley, Calif.: Transform Press. In one embodiment, a  serotonergic drug is chosen from alprazolam, amphetamine, aripiprazole, azapirone, a barbiturate,  bromazepam, bupropion, buspirone, a cannabinoid, chlordiazepoxide, citalopram, clonazepam,  clorazepate, dextromethorphan, diazepam, duloxetine, escitalopram, fluoxetine, flurazepam,  fluvoxamine, lorazepam, lysergic acid diethylamide, lysergamide, 3,4‐ methylenedioxymethamphetamine, milnacipran, mirtazapine, naratriptan, paroxetine, pethidine,  phenethylamine, psicaine, oxazepam, reboxetine, serenic, serotonin, sertraline, temazepam,  tramadol, triazolam, a tryptamine, venlafaxine, vortioxetine, and/or derivatives thereof. In an  exemplary embodiment, the serotonergic drug is 3,4‐methylenedioxymethamphetamine.     [137] Exemplary psilocybin derivatives include but are not limited to psilocybin itself and the  psilocybin derivatives described in paragraphs [0081]‐[0109] of US 2018/0221396 A1 and [0082]‐ [0110] US 2019/0142851 A1 as well as the disclosed exemplary embodiments, incorporated here by  reference. In one embodiment, the compositions disclosed herein comprise one or more purified  psilocybin derivatives chosen from: [3‐(2‐dimethylaminoethyl)‐1H‐indol‐4‐yl] dihydrogen phosphate;  4‐hydroxytryptamine; 4‐hydroxy‐N,N‐dimethyltryptamine; [3‐(2‐methylaminoethyl)‐1H‐indol‐4‐yl]  dihydrogen phosphate; 4‐hydroxy‐N‐methyltryptamine; [3‐(aminoethyl)‐1H‐indol‐4‐yl] dihydrogen  phosphate; [3‐(2‐trimethylaminoethyl)‐1H‐indol‐4‐yl] dihydrogen phosphate; and 4‐hydroxy‐N,N,N‐ trimethyltryptamine.   [138] Exemplary cannabinoids include but are not limited to the cannabinoids described in  paragraphs [0111]‐[0145] of US 2018/0221396 A1 and [0112]‐[0146] US 2019/0142851 A1 as well as  the disclosed exemplary embodiments. Examples of cannabinoids within the context of this  disclosure include the following molecules: cannabichromene (CBC); cannabichromenic acid (CBCA);  cannabichromevarin (CBCV); cannabichromevarinic acid (CBCVA); cannabicyclol (CBL);  cannabicyclolic acid (CBLA); cannabicyclovarin (CBLV); cannabidiol (CBD); cannabidiol  monomethylether (CBDM); cannabidiolic acid (CBDA); cannabidiorcol (CBD‐C1); cannabidivarin  (CBDV); cannabidivarinic acid (CBDVA); cannabielsoic acid B (CBEA‐B); cannabielsoin (CBE);  cannabielsoin acid A (CBEA‐A); cannabigerol (CBG); cannabigerol monomethylether (CBGM);  cannabigerolic acid (CBGA); cannabigerolic acid monomethylether (CBGAM); cannabigerovarin  (CBGV); cannabigerovarinic acid (CBGVA); cannabinodiol (CBND); cannabinodivarin (CBVD);  cannabinol (CBN); cannabinol methylether (CBNM); cannabinol‐C2 (CBN‐C2); cannabinol‐C4 (CBN‐ C4); cannabinolic acid (CBNA); cannabiorcol (CBN‐C1); cannabivarin (CBV); cannabitriol (CBT);  cannabitriolvarin (CBTV); 10‐ethoxy‐9‐hydroxy‐delta‐6a‐tetrahydrocannabinol; cannabicitran (CBTC);  cannabiripsol (CBR); 8,9‐dihydroxy‐delta‐6a‐tetrahydrocannabinol; delta‐8‐tetrahydrocannabinol  (Δ8‐THC); delta‐8‐tetrahydrocannabinolic acid (Δ8‐THCA); delta‐9‐tetrahydrocannabinol (THC); delta‐ 9‐tetrahydrocannabinol‐C4 (THC‐C4); delta‐9‐tetrahydrocannabinolic acid A (THCA‐A); delta‐9‐ tetrahydrocannabinolic acid B (THCA‐B); delta‐9‐tetrahydrocannabinolic acid‐C4 (THCA‐C4); delta‐9‐ tetrahydrocannabiorcol (THC‐C1); delta‐9‐tetrahydrocannabiorcolic acid (THCA‐C1); delta‐9‐ tetrahydrocannabivarin (THCV); delta‐9‐tetrahydrocannabivarinic acid (THCVA); 10‐oxo‐delta‐6a‐ tetrahydrocannabinol (OTHC); cannabichromanon (CBCF); cannabifuran (CBF); cannabiglendol;  delta‐9‐cis‐tetrahydrocannabinol (cis‐THC); trihydroxy‐delta‐9‐tetrahydrocannabinol (triOH‐THC);  dehydrocannabifuran (DCBF); and 3,4,5,6‐tetrahydro‐7‐hydroxy‐alpha‐alpha‐2‐trimethyl‐9‐n‐propyl‐ 2,6‐methano‐2H‐1‐benzoxocin‐5‐methanol. In one embodiment, the purified cannabinoid is chosen    from THC, THCA, THCV, THCVA, CBC, CBCA, CBCV, CBCVA, CBD, CBDA, CBDV, CBVD, CBDVA, CBG,  CBGA, CBGV, or CBGVA.  [139] Exemplary terpenes include but are not limited to the terpenes described in paragraphs  [0160]‐[0238] of US 2018/0221396 A1 and [0161]‐[0300] US 2019/0142851 A1 as well as the  disclosed exemplary embodiments. In one embodiment, a purified terpene is chosen from  acetanisole, acetyl cedrene, anethole, anisole, benzaldehyde, bornyl acetate, borneol, cadinene,  cafestol, caffeic acid, camphene, camphor, capsaicin, carene, carotene, carvacrol, carvone,  caryophyllene, caryophyllene, caryophyllene oxide, cedrene, cedrene epoxide, cecanal, cedrol,  cembrene, cinnamaldehyde, cinnamic acid, citronellal, citronellol, cymene, eicosane, elemene,  estragole, ethyl acetate, ethyl cinnamate, ethyl maltol, eucalyptol/1,8‐cineole, eudesmol, eugenol,  euphol, farnesene, farnesol, fenchone, geraniol, geranyl acetate, guaia‐1(10),11‐diene, guaiacol,  guaiol, guaiene, gurjunene, herniarin, hexanaldehyde, hexanoic acid, humulene, ionone, ipsdienol,  isoamyl acetate, isoamyl alcohol, isoamyl formate, isoborneol, isomyrcenol, isoprene, isopulegol,  isovaleric acid, lavandulol, limonene, gamma‐linolenic acid, linalool, longifolene, lycopene, menthol,  methyl butyrate, 3‐mercapto‐2‐methylpentanal, beta‐mercaptoethanol, mercaptoacetic acid, methyl  salicylate, methylbutenol, methyl‐2‐methylvalerate, methyl thiobutyrate, myrcene, gamma‐ muurolene, nepetalactone, nerol, nerolidol, neryl acetate, nonanaldehyde, nonanoic acid, ocimene,  octanal, octanoic acid, pentyl butyrate, phellandrene, phenylacetaldehyde, phenylacetic acid,  phenylethanethiol, phytol, pinene, propanethiol, pristimerin, pulegone, retinol, rutin, sabinene,  squalene, taxadiene, terpineol, terpine‐4‐ol, terpinolene, thujone, thymol, umbelliferone, undecanal,  verdoxan, or vanillin. In one embodiment, a purified terpene is chosen from bornyl acetate, alpha‐ bisabolol, borneol, camphene, camphor, carene, caryophyllene, cedrene, cymene, elemene,  eucalyptol, eudesmol, farnesene, fenchol, geraniol, guaiacol, humulene, isoborneol, limonene,  linalool, menthol, myrcene, nerolidol, ocimene, phellandrene, phytol, pinene, pulegone, sabinene,  terpineol, terpinolene, or valencene.  [140] As used herein, the term “adrenergic drug” refers to a compound that binds, blocks, or  otherwise influences (e.g., via an allosteric reaction) activity at an adrenergic receptor. In one  embodiment, an adrenergic drug binds to an adrenergic receptor. In one embodiment, an adrenergic  drug indirectly affects an adrenergic receptor, e.g., via interactions affecting the reactivity of other  molecules at the adrenergic receptor. In one embodiment, an adrenergic drug is an agonist, e.g., a  compound activating an adrenergic receptor. In one embodiment, an adrenergic drug is an  antagonist, e.g., a compound binding but not activating an adrenergic receptor, e.g., blocking a  receptor. In one embodiment, an adrenergic drug is an effector molecule, e.g., a compound binding  to an enzyme for allosteric regulation. In one embodiment, an adrenergic drug acts (either directly    or indirectly) at more than one type of receptor (e.g., 5HT, dopamine, adrenergic, acetylcholine,  etc.).  [141] In one embodiment, an adrenergic drug is an antidepressant. In one embodiment, an  adrenergic drug is a norepinephrine transporter inhibitor. In one embodiment, an adrenergic drug is  a vesicular monoamine transporter inhibitor. In one embodiment, an adrenergic drug is chosen from  adrenaline, agmatine, amoxapine, aptazapine, atomoxetine, bupropion, clonidine, doxepin,  duloxetine, esmirtazpine, mianserin, ketanserin, mirabegron, mirtazapine, norepinephrine,  phentolamine, phenylephrine, piperoxan, reserpine, ritodrine, setiptiline, tesofensine, timolol,  trazodone, trimipramine, or xylazine.  [142] As used herein, the term “dopaminergic drug” refers to a compound that binds, blocks, or  otherwise influences (e.g., via an allosteric reaction) activity at a dopamine receptor. In one  embodiment, a dopaminergic drug binds to a dopamine receptor. In one embodiment, a  dopaminergic drug indirectly affects a dopamine receptor, e.g., via interactions affecting the  reactivity of other molecules at the dopamine receptor. In one embodiment, a dopaminergic drug is  an agonist, e.g., a compound activating a dopamine receptor. In one embodiment, a dopaminergic  drug is an antagonist, e.g., a compound binding but not activating a dopamine receptor, e.g.,  blocking a receptor. In one embodiment, a dopaminergic drug is an effector molecule, e.g., a  compound binding to an enzyme for allosteric regulation. In one embodiment, a dopaminergic drug  acts (either directly or indirectly) at more than one type of receptor (e.g., 5HT, dopamine,  adrenergic, acetylcholine, etc.).  [143] In one embodiment, a dopaminergic drug is a dopamine transporter inhibitor. In one  embodiment, a dopaminergic drug is a vesicular monoamine transporter inhibitor. In one  embodiment, a dopaminergic drug is chosen from amineptine, apomorphine, benzylpiperazine,  bromocriptine, cabergoline, chlorpromazine, clozapine, dihydrexidine, domperidone, dopamine,  fluphenazine, haloperidol, ketamine, loxapine, methamphetamine, olanzapine, pemoline,  perphenazine, pergolide, phencyclidine, phenethylamine, phenmetrazine, pimozide, piribedil, a  psychostimulant, reserpine, risperidone, ropinirole, tetrabenazine, or thioridazine.  [144] As used herein, the term “monoamine oxidase inhibitor” (MAOI) refers to a compound that  blocks the actions of monoamine oxidase enzymes. In one embodiment, a MAOI inhibits the activity  of one or both monoamine oxidase A and monoamine oxidase B. In one embodiment a MAOI is a  reversible inhibitor of monoamine oxidase A. In one embodiment a MAOI is a drug chosen from  isocarboxazid, phenelzine, or tranylcypromine. In one embodiment, a MAOI is β‐carboline, pinoline,  harmane, harmine, harmaline, harmalol, tetrahydroharmine, 9‐methyl‐β‐carboline, or 3‐carboxy‐ tetrahydrononharman.     [145] In one embodiment, the compositions and methods disclosed herein include one or more  purified erinacine molecules. In one embodiment, the compositions and methods disclosed herein  comprise purified erinacine A. In one embodiment, the compositions and methods disclosed herein  comprise erinacine B. In one embodiment, the compositions and methods disclosed herein comprise  erinacine C. In one embodiment, the compositions and methods disclosed herein comprise erinacine  D. In one embodiment, the compositions and methods disclosed herein comprise erinacine E. In one  embodiment, the compositions and methods disclosed herein comprise erinacine F. In one  embodiment, the compositions and methods disclosed herein comprise erinacine G. In one  embodiment, the compositions and methods disclosed herein comprise erinacine H. In one  embodiment, the compositions and methods disclosed herein comprise erinacine I. In one  embodiment, the compositions and methods disclosed herein comprise erinacine J. In one  embodiment, the compositions and methods disclosed herein comprise erinacine K In one  embodiment, the compositions and methods disclosed herein comprise erinacine P. In one  embodiment, the compositions and methods disclosed herein comprise erinacine Q. In one  embodiment, the compositions and methods disclosed herein comprise erinacine R. In one  embodiment, the compositions and methods disclosed herein comprise erinacine S.   [146] In one embodiment, the compositions and methods disclosed herein include one or more  purified hericenone molecules. In one embodiment, the compositions and methods disclosed herein  comprise purified hericenone A. In one embodiment, the compositions and methods disclosed  herein comprise purified hericenone B. In one embodiment, the compositions and methods  disclosed herein comprise purified hericenone C. In one embodiment, the compositions and  methods disclosed herein comprise purified hericenone D. In one embodiment, the compositions  and methods disclosed herein comprise purified hericenone E. In one embodiment, the  compositions and methods disclosed herein comprise purified hericenone F. In one embodiment,  the compositions and methods disclosed herein comprise purified hericenone G. In one  embodiment, the compositions and methods disclosed herein comprise purified hericenone H.   [147] Exemplary compositions of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate,  tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium  hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐ MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐ 5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T  hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐ T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT  fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT    hydrofumarate or specific crystalline forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate,  crystalline form 1 of tryptammonium hydromalate, crystalline form 1 of tryptammonium  hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT  hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate,  crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of  5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate,  and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the disclosure and a second compound  selected from a serotonergic drug, a purified psilocybin derivative, a purified cannabinoid, a purified  terpene, an adrenergic drug, a dopaminergic drug, a monoamine oxidase inhibitor, a purified  erinacine, and a purified hericenone in exemplary molar ratios are shown in Tables 1a and 1b. 5‐ MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline  tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium  hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT  hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T  hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be any one of the exemplary embodiments described above  including the crystalline forms as disclosed herein.  Table 1a 
Figure imgf000048_0001
 
Figure imgf000049_0001
 
Figure imgf000050_0001
 
Figure imgf000051_0001
 
Figure imgf000052_0001
 
Figure imgf000053_0001
 
Figure imgf000054_0001
 
Figure imgf000055_0001
  Table 1b 
Figure imgf000055_0002
 
Figure imgf000056_0001
 
Figure imgf000057_0001
 
Figure imgf000058_0001
 
Figure imgf000059_0001
 
Figure imgf000060_0001
 
Figure imgf000061_0001
  [148] Exemplary pharmaceutical compositions of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T  fumarate, tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium  hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐ MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐ 5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T  hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐ T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT  fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT  hydrofumarate or specific crystalline forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate,  crystalline form 1 of tryptammonium hydromalate, crystalline form 1 of tryptammonium  hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT  hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate,  crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of  5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate,  and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the disclosure and a second compound  selected from a serotonergic drug, a purified psilocybin derivative, a purified cannabinoid, a purified  terpene, an adrenergic drug, a dopaminergic drug, a monoamine oxidase inhibitor, a purified  erinacine, and a purified hericenone and an excipient with exemplary molar ratios of 5‐MeO‐T  fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐   T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate to the second  compound are shown in Tables 2a and 2b. 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate,  tryptammonium hydromalate, crystalline tryptammonium hydromalate, tryptammonium  hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐ MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐ 5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T  hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐ T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT  fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT  hydrofumarate or specific crystalline forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate,  crystalline form 1 of tryptammonium hydromalate, crystalline form 1 of tryptammonium  hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT  hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate,  crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of  5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate,  and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the disclosure may be any one of the  exemplary embodiments described above including the crystalline forms as disclosed herein.  Table 2a 
Figure imgf000062_0001
 
Figure imgf000063_0001
 
Figure imgf000064_0001
 
Figure imgf000065_0001
 
Figure imgf000066_0001
 
Figure imgf000067_0001
 
Figure imgf000068_0001
 
Figure imgf000069_0001
  Table 2b 
Figure imgf000069_0002
 
Figure imgf000070_0001
 
Figure imgf000071_0001
 
Figure imgf000072_0001
 
Figure imgf000073_0001
 
Figure imgf000074_0001
  [149] An “effective amount” or a “therapeutically effective amount” of 5‐MeO‐T fumarate,  crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,    crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the disclosure  is generally in the range of about 0.1 to about 100 mg daily (oral dose), of about 0.1 to about 50 mg  daily (oral dose), of about 0.25 to about 25 mg daily (oral dose), of about 0.1 to about 5 mg daily  (oral dose), or of about 0.5 to about 2.5 mg daily (oral dose). The actual amount required for  treatment of any particular patient may depend upon a variety of factors including, for example, the  disease being treated and its severity; the specific pharmaceutical composition employed; the age,  body weight, general health, sex, and diet of the patient; the mode of administration; the time of  administration; the route of administration; and the rate of excretion; the duration of the treatment;  any drugs used in combination or coincidental with the specific compound employed; and other  such factors well known in the medical arts. These factors are discussed in Goodman and Gilman’s  “The Pharmacological Basis of Therapeutics,” Tenth Edition, A. Gilman, J. Hardman and L. Limbird,  eds., McGraw‐Hill Press, 155‐173 (2001), which is incorporated herein by reference. 5‐MeO‐T  fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate, crystalline tryptammonium  hydromalate, tryptammonium hydrophthalate, crystalline tryptammonium hydrophthalate, 4‐MeO‐ MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐PiPT hydrofumarate, crystalline 4‐HO‐PiPT  hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline  5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐Cl‐T hydrophthalate, 5‐Cl‐T malate,  crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T,  crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT fumarate, 4‐HO‐DiPT  hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline forms thereof, such as  crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium hydromalate,  crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐MiPT fumarate,  crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline  form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate, crystalline form 1 of 5‐Cl‐ T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1 of 5‐Me‐T, crystalline  form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT hydrofumarate of the disclosure    and pharmaceutical compositions containing it may be used in combination with other agents that  are generally administered to a patient being treated for psychological and other disorders discussed  above. They may also be co‐formulated with one or more of such agents in a single pharmaceutical  composition.  [150] Depending on the type of pharmaceutical composition, the pharmaceutically acceptable  carrier may be chosen from any one or a combination of carriers known in the art. The choice of the  pharmaceutically acceptable carrier depends upon the pharmaceutical form and the desired method  of administration to be used. Exemplary carriers include those that do not substantially alter the  structure or activity of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium  hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure, or produce undesirable biological effects or otherwise interact in a  deleterious manner with any other component(s) of the pharmaceutical composition.  [151] The pharmaceutical compositions of the disclosure may be prepared by methods know in  the pharmaceutical formulation art, for example, see Remington’s Pharmaceutical Sciences, 18th  Ed., (Mack Publishing Company, Easton, Pa., 1990), which is incorporated herein by reference. In a  solid dosage form, 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium hydromalate,  crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT    fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure may be admixed with at least one pharmaceutically acceptable  excipient such as, for example, sodium citrate or dicalcium phosphate or (a) fillers or extenders, such  as, for example, starches, lactose, sucrose, glucose, mannitol, and silicic acid, (b) binders, such as, for  example, cellulose derivatives, starch, alginates, gelatin, polyvinylpyrrolidone, sucrose, and gum  acacia, (c) humectants, such as, for example, glycerol, (d) disintegrating agents, such as, for example,  agar‐agar, calcium carbonate, potato or tapioca starch, alginic acid, croscarmellose sodium, complex  silicates, and sodium carbonate, (e) solution retarders, such as, for example, paraffin, (f) absorption  accelerators, such as, for example, quaternary ammonium compounds, (g) wetting agents, such as,  for example, cetyl alcohol, and glycerol monostearate, magnesium stearate and the like,  (h) adsorbents, such as, for example, kaolin and bentonite, and (i) lubricants, such as, for example,  talc, calcium stearate, magnesium stearate, solid polyethylene glycols, sodium lauryl sulfate, or  mixtures thereof. In the case of capsules, tablets, and pills, the dosage forms may also comprise  buffering agents. In some embodiments, the excipient is not water. In some embodiments, the  excipient is not a solvent (e.g., EtOH, diethyl ether, ethyl acetate, or hydrocarbon‐based solvents  (e.g., hexanes). In some embodiments, the dosage form is substantially free of water and/or  solvents, for example less than about 5% water by mass, less than 2% water by mass, less than 1%  water by mass, less than 0.5% water by mass, or less than 0.1% water by mass.  [152] Excipients or pharmaceutically acceptable adjuvants known in the pharmaceutical  formulation art may also be used in the pharmaceutical compositions of the disclosure. These  include, but are not limited to, preserving, wetting, suspending, sweetening, flavoring, perfuming,  emulsifying, and dispensing agents. Prevention of the action of microorganisms may be ensured by  inclusion of various antibacterial and antifungal agents, for example, parabens, chlorobutanol,  phenol, sorbic acid, and the like. It may also be desirable to include isotonic agents, for example,  sugars, sodium chloride, and the like. If desired, a pharmaceutical composition of the disclosure may  also contain minor amounts of auxiliary substances such as wetting or emulsifying agents, pH  buffering agents, antioxidants, and the like, such as, for example, citric acid, sorbitan monolaurate,  triethanolamine oleate, butylated hydroxytoluene, etc.    [153] Solid dosage forms as described above may be prepared with coatings and shells, such as  enteric coatings and others well known in the art. They may contain pacifying agents and can also be  of such composition that they release the active compound or compounds in a certain part of the  intestinal tract in a delayed manner. Non‐limiting examples of embedded compositions that may be  used are polymeric substances and waxes. The active compounds may also be in microencapsulated  form, if appropriate, with one or more of the above‐mentioned excipients.   [154] Suspensions, in addition to the active compounds, may contain suspending agents, such as,  for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters,  microcrystalline cellulose, aluminum metahydroxide, bentonite, agar‐agar and tragacanth, or  mixtures of these substances, and the like.  [155] Solid dosage forms for oral administration, which includes capsules, tablets, pills, powders,  and granules, may be used. In such solid dosage forms, the active compound may be mixed with at  least one inert, pharmaceutically acceptable excipient (also known as a pharmaceutically acceptable  carrier).   [156] Administration of 5‐MeO‐T fumarate, crystalline 5‐MeO‐T fumarate, tryptammonium  hydromalate, crystalline tryptammonium hydromalate, tryptammonium hydrophthalate, crystalline  tryptammonium hydrophthalate, 4‐MeO‐MiPT fumarate, crystalline 4‐MeO‐MiPT fumarate, 4‐HO‐ PiPT hydrofumarate, crystalline 4‐HO‐PiPT hydrofumarate, 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, crystalline 5‐Cl‐T∙N‐ Suc‐5‐Cl‐T, 5‐Cl‐T hydromaleate, crystalline 5‐Cl‐T hydromaleate, 5‐Cl‐T hydrophthalate, crystalline 5‐ Cl‐T hydrophthalate, 5‐Cl‐T malate, crystalline 5‐Cl‐T malate, 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline 5‐ MeO‐T∙N‐Suc‐5‐MeO‐T, 5‐Me‐T, crystalline 5‐Me‐T, 4‐HO‐MCPT fumarate, crystalline 4‐HO‐MCPT  fumarate, 4‐HO‐DiPT hydrofumarate, crystalline 4‐HO‐DiPT hydrofumarate or specific crystalline  forms thereof, such as crystalline form 1 of 5‐MeO‐T fumarate, crystalline form 1 of tryptammonium  hydromalate, crystalline form 1 of tryptammonium hydrophthalate, crystalline form 1 of 4‐MeO‐ MiPT fumarate, crystalline form 1 of 4‐HO‐PiPT hydrofumarate, crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐ Cl‐T, crystalline form 1 of 5‐Cl‐T hydromaleate, crystalline form 1 of 5‐Cl‐T hydrophthalate,  crystalline form 1 of 5‐Cl‐T malate, crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T, crystalline form 1  of 5‐Me‐T, crystalline form 1 of 4‐HO‐MCPT fumarate, and crystalline form 1 of 4‐HO‐DiPT  hydrofumarate of the disclosure in pure form or in an appropriate pharmaceutical composition may  be carried out via any of the accepted modes of administration or agents for serving similar utilities.  Thus, administration may be, for example, orally, buccally, nasally, parenterally (intravenous,  intramuscular, or subcutaneous), topically, transdermally, intravaginally, intravesically, or  intrasystemically, in the form of solid, semi‐solid, lyophilized powder, or liquid dosage forms, such  as, for example, tablets, suppositories, pills, soft elastic and hard gelatin capsules, powders,    solutions, suspensions, or aerosols, or the like, such as, for example, in unit dosage forms suitable  for simple administration of precise dosages. One route of administration may be oral  administration, using a convenient daily dosage regimen that can be adjusted according to the  degree of severity of the disease‐state to be treated.   [157] Exemplary Embodiments of the Invention  [158] E1. Bis(2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐enedioate (5‐ methoxytryptammonium fumarate).  [159] E2. Crystalline bis(2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐enedioate (5‐ methoxytryptammonium fumarate).  [160] E3. Crystalline form 1 of bis(2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐ enedioate (5‐methoxytryptammonium fumarate).  [161] E4. Crystalline form 1 of 5‐methoxytryptammonium fumarate according to E3, characterized  by at least one of:    a monoclinic crystal system at a temperature of about 297 K;    a P21/c  space group at a temperature of about 297 K;    unit cell dimensions a = 5.8070(3) Å, b = 24.2768(13) Å, c = 8.9334(5) Å, α = 90°, β =  103.360(2)°, and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 30; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 7.3,  12.5, and 24.8 °2θ ± 0.2 °2θ.  [162] E5. A composition comprising 5‐methoxytryptammonium fumarate according to E1 and an  excipient.  [163] E6. A composition comprising crystalline 5‐methoxytryptammonium fumarate according to  any one of E2‐E4 and an excipient.  [164] E7. A composition comprising 5‐methoxytryptammonium fumarate according to E1 as a first  component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.  [165] E8. A composition comprising crystalline 5‐methoxytryptammonium fumarate according to  any one of E2‐E4 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    [166] E9. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ methoxytryptammonium fumarate according to E1.  [167] E10. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ methoxytryptammonium fumarate according to any one of E2‐E4.  [168] E11. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E5 or E7.  [169] E12. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E6 or E8.  [170] E13. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ methoxytryptammonium fumarate according to E1.  [171] E14. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ methoxytryptammonium fumarate according to any one of E2‐E4.  [172] E15. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E5 or E7.  [173] E16. A method of preventing or treating inflammation and/or pain comprising the step of:  administering to a subject in need thereof a composition according to E6 or E8.  [174] E17. 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate (tryptammonium  hydromalate).  [175] E18. Crystalline 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate  (tryptammonium hydromalate)  [176] E19. Crystalline form 1 of 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate  (tryptammonium hydromalate).  [177] E20. Crystalline form 1 of tryptammonium hydromalate according to E19, characterized by  at least one of:    an orthorhombic crystal system at a temperature of about 297 K;    a P212121 space group at a temperature of about 297 K;    unit cell dimensions a = 7.2012(5) Å, b = 8.2509(5) Å, c = 24.7541(16) Å, α = 90°, β = 90°, and  ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 31; or      an X‐ray powder diffraction pattern characterized by at least two peaks selected from 7.1,  11.3, and 20.9 °2θ ± 0.2 °2θ.  [178] E21. A composition comprising tryptammonium hydromalate according to E17 and an  excipient.  [179] E22. A composition comprising crystalline tryptammonium hydromalate according to any  one of E18‐E20 and an excipient.  [180] E23. A composition comprising tryptammonium hydromalate according to E17 as a first  component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.  [181] E24. A composition comprising crystalline tryptammonium hydromalate according to any  one of E18‐E20 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.  [182] E25. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of  tryptammonium hydromalate according to E17.  [183] E26. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline  tryptammonium hydromalate according to any one of E18‐E20.  [184] E27. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E21 or E23.  [185] E28. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E22 or E24.  [186] E29. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of  tryptammonium hydromalate according to E17.  [187] E30. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline  tryptammonium hydromalate according to any one of E18‐E20.  [188] E31. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E21 or E23.    [189] E32. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E22 or E24.  [190] E33. 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (tryptammonium  hydrophthalate).  [191] E34. Crystalline 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (tryptammonium  hydrophthalate).  [192] E35. Crystalline form 1 of 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate  (tryptammonium hydrophthalate).  [193] E36. Crystalline form 1 of tryptammonium hydrophthalate according to E35, characterized  by at least one of:    a monoclinic crystal system at a temperature of about 297 K;    a C2/c space group at a temperature of about 297 K;    unit cell dimensions a = 18.7823(11) Å, b = 5.7731(3) Å, c = 29.3825(19) Å, α = 90°, β =  90.617(2)°, and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 32; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 6.0,  11.2, and 15.4 °2θ ± 0.2 °2θ.  [194] E37. A composition comprising tryptammonium hydrophthalate according to E33 and an  excipient.  [195] E38. A composition comprising crystalline tryptammonium hydrophthalate according to any  one of E34‐E36 and an excipient.  [196] E39. A composition comprising tryptammonium hydrophthalate according to E33 as a first  component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.  [197] E40. A composition comprising crystalline tryptammonium hydrophthalate according to any  one of E34‐E36 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.  [198] E41. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of  tryptammonium hydrophthalate according to E33.    [199] E42. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline  tryptammonium hydrophthalate according to any one of E34‐E36.  [200] E43. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E37 or E39.  [201] E44. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E38 or E40.  [202] E45. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of  tryptammonium hydrophthalate according to E33.  [203] E46. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline  tryptammonium hydrophthalate according to any one of E34‐E36.  [204] E47. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E37 or E39.  [205] E48. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E38 or E40.  [206] E49. Bis([2‐(4‐methoxy‐1H‐indol‐3‐yl)ethyl](methyl)(propan‐2‐yl)azanium) (2E)‐but‐2‐ enedioate (4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate).  [207] E50. Crystalline bis([2‐(4‐methoxy‐1H‐indol‐3‐yl)ethyl](methyl)(propan‐2‐yl)azanium) (2E)‐ but‐2‐enedioate (4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate).  [208] E51. Crystalline form 1 of bis([2‐(4‐methoxy‐1H‐indol‐3‐yl)ethyl](methyl)(propan‐2‐ yl)azanium) (2E)‐but‐2‐enedioate (4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate).  [209] E52. Crystalline form 1 of 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate  according to E51, characterized by at least one of:    a monoclinic crystal system at a temperature of about 297 K;    a P21/n space group at a temperature of about 297 K;    unit cell dimensions a = 9.1438(3) Å, b = 13.8957(6) Å, c = 13.6658(6) Å, α = 90°, β =  94.6140(10)°, and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG.33; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 9.1,  14.5, and 16.0 °2θ ± 0.2 °2θ.  [210] E53. A composition comprising 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate  according to E49 and an excipient.    [211] E54. A composition comprising crystalline 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium  fumarate according to any one of E50‐E52 and an excipient.  [212] E55. A composition comprising 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate  according to E49 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.  [213] E56. A composition comprising crystalline 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium  fumarate according to any one of E50‐E52 as a first component and a second component selected  from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified  cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a  monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.  [214] E57. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 4‐methoxy‐ N‐methyl‐N‐isopropyltryptammonium fumarate according to E49.  [215] E58. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 4‐ methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate according to any one of E50‐E52.  [216] E59. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E53 or E55.  [217] E60. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E54 or E56.  [218] E61. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 4‐methoxy‐ N‐methyl‐N‐isopropyltryptammonium fumarate according to E49.  [219] E62. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 4‐ methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate according to any one of E50‐E52.  [220] E63. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E53 or E55.  [221] E64. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E54 or E56.  [222] E65. Crystalline [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl](propan‐2‐yl)propylazanium (2E)‐3‐ carboxyprop‐2‐enoate (4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate).    [223] E66. Crystalline form 1 of [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl](propan‐2‐yl)propylazanium (2E)‐ 3‐carboxyprop‐2‐enoate (4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate).  [224] E67. Crystalline form 1 of 4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate  according to claim E66, characterized by at least one of:    an orthorhombic crystal system at a temperature of about 297 K;    a P212121 space group at a temperature of about 297 K;    unit cell dimensions a = 7.8854(7) Å, b = 12.7401(11) Å, c = 20.5577(18) Å, α = 90°, β = 90°,  and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 34; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 11.1,  12.0, and 15.8 °2θ ± 0.2 °2θ.  [225] E68. A composition comprising crystalline 4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium  hydrofumarate according to any one of E65‐E67 and an excipient.  [226] E69. A composition comprising crystalline 4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium  hydrofumarate according to any one of E65‐E67 as a first component and a second component  selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified  cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a  monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.  [227] E70. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 4‐ hyroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate according to any one of E65‐E67.  [228] E71. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E68 or E69.  [229] E72. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 4‐ hyroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate according to any one of E65‐E67.  [230] E73. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E68 or E69.  [231] E74. 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐chloro‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium).  [232] E75. Crystalline 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐chloro‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium).    [233] E76. Crystalline form 1 of 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐chloro‐1H‐ indol‐3‐yl)ethyl]azaniumyl}butanedioate (5‐chlorotryptammonium N‐succinyl‐5‐ chlorotryptammonium).  [234] E77. Crystalline form 1 of 5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium  according to E76, characterized by at least one of:    a triclinic crystal system at a temperature of about 300 K;    a P1 ത  space group at a temperature of about 300 K;    unit cell dimensions a = 9.5806(13) Å, b = 11.1666(14) Å, c = 11.5518(17) Å, α = 87.333(5)°, β  = 74.347(5)°, and ɣ = 85.637(5)°;    an X‐ray powder diffraction pattern substantially similar to FIG. 35; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 12.8,  15.9, and 22.9 °2θ ± 0.2 °2θ.  [235] E78. A composition comprising 5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium  according to E74 and an excipient.  [236] E79. A composition comprising crystalline 5‐chlorotryptammonium N‐succinyl‐5‐ chlorotryptammonium according to any one of E75‐E77 and an excipient.  [237] E80. A composition comprising 5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium  according to E74 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.  [238] E81. A composition comprising crystalline 5‐chlorotryptammonium N‐succinyl‐5‐ chlorotryptammonium according to any one of E75‐E77 as a first component and a second  component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative,  (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g)  a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.  [239] E82. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium according to E74.  [240] E83. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium according to any one of E75‐E77.  [241] E84. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E78 or E80.    [242] E85. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E79 or E81.  [243] E86. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium according to E74.  [244] E87. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium according to any one of E75‐E77.  [245] E88. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E78 or E80.  [246] E89. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E79 or E81.  [247] E90. 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate (5‐ chlorotryptammonium hydromaleate).  [248] E91. Crystalline 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate  (5‐chlorotryptammonium hydromaleate).  [249] E92. Crystalline form 1 of 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐ hydroxypropanoate (5‐chlorotryptammonium hydromaleate).  [250] E93. Crystalline form 1 of 5‐chlorotryptammonium hydromaleate according to E92,  characterized by at least one of:    a monoclinic crystal system at a temperature of about 300 K;    a P21/c space group at a temperature of about 300 K;    unit cell dimensions a = 9.6320(7) Å, b = 5.4224(4) Å, c = 28.494(2) Å, α = 90°, β = 95.758(3)°,  and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 36; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 9.2,  10.6, and 14.8 °2θ ± 0.2 °2θ.  [251] E94. A composition comprising 5‐chlorotryptammonium hydromaleate according to E90 and  an excipient.  [252] E95. A composition comprising crystalline 5‐chlorotryptammonium hydromaleate according  to any one of E91‐E93 and an excipient.  [253] E96. A composition comprising 5‐chlorotryptammonium hydromaleate according to E90 as a  first component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic    drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.  [254] E97. A composition comprising crystalline 5‐chlorotryptammonium hydromaleate according  to any one of E91‐E93 as a first component and a second component selected from at least one of  (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.  [255] E98. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ chlorotryptammonium hydromaleate according to E90.  [256] E99. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ chlorotryptammonium hydromaleate according to any one of E91‐E93.  [257] E100. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E94 or E96.  [258] E101. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E95 or E97.  [259] E102. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ chlorotryptammonium hydromaleate according to E90.  [260] E103. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ chlorotryptammonium hydromaleate according to any one of E91‐E93.  [261] E104. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E94 or E96.  [262] E105. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E95 or E97.  [263] E106. 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (5‐ chlorotryptammonium hydrophthalate).  [264] E107. Crystalline 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (5‐ chlorotryptammonium hydrophthalate).  [265] E108. Crystalline form 1 of 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate  (5‐chlorotryptammonium hydrophthalate).    [266] E109. Crystalline form 1 of 5‐chlorotryptammonium hydrophthalate according to E108,  characterized by at least one of:    a triclinic crystal system at a temperature of about 300 K;    a P1 ത   space group at a temperature of about 300 K;    unit cell dimensions a = 7.4013(6) Å, b = 9.8217(9) Å, c = 12.1614(12) Å, α = 83.285(3)°, β =  79.601(3)°, and ɣ = 78.437(3)°;    an X‐ray powder diffraction pattern substantially similar to FIG. 37; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 11.3,  12.3, and 15.4 °2θ ± 0.2 °2θ.  [267] E110. A composition comprising 5‐chlorotryptammonium hydrophthalate according to E106  and an excipient.  [268] E111. A composition comprising crystalline 5‐chlorotryptammonium hydrophthalate  according to any one of E107‐E109 and an excipient.  [269] E112. A composition comprising 5‐chlorotryptammonium hydrophthalate according to E106  as a first component and a second component selected from at least one of (a) a serotonergic drug,  (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an  adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine,  and (i) a purified hericenone.  [270] E113. A composition comprising crystalline 5‐chlorotryptammonium hydrophthalate  according to any one of E107‐E109 as a first component and a second component selected from at  least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d)  a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase  inhibitor, (h) a purified erinacine, and (i) a purified hericenone.  [271] E114. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ chlorotryptammonium hydrophthalate according to E106.  [272] E115. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ chlorotryptammonium hydrophthalate according to any one of E107‐E109.  [273] E116. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E110 or E112.  [274] E117. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E111 or E113.  [275] E118. A method of preventing or treating inflammation and/or pain comprising the step of:      administering to a subject in need thereof a therapeutically effective amount of 5‐ chlorotryptammonium hydrophthalate according to E106.  [276] E119. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ chlorotryptammonium hydrophthalate according to any one of E107‐E109.  [277] E120. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E110 or E112.  [278] E121. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E111 or E113.  [279] E122. Bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium) 2‐hydroxybutanedioate (5‐ chlorotryptammonium malate).  [280] E123. Crystalline bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium) 2‐hydroxybutanedioate (5‐ chlorotryptammonium malate).  [281] E124. Crystalline form 1 of bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium) 2‐ hydroxybutanedioate (5‐chlorotryptammonium malate).  [282] E125. Crystalline form 1 of 5‐chlorotryptammonium malate according to E124, characterized  by at least one of:    a monoclinic crystal system at a temperature of about 300 K;    a P21 space group at a temperature of about 300 K;    unit cell dimensions a = 8.9975(8) Å, b = 12.3798(12) Å, c = 11.3628(11) Å, α = 90°, β =  106.617(3)°, and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 38; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 12.5,  13.2, and 14.3 °2θ ± 0.2 °2θ.  [283] E126. A composition comprising 5‐chlorotryptammonium malate according to E122 and an  excipient.  [284] E127. A composition comprising crystalline 5‐chlorotryptammonium malate according to any  one of E123‐E125 and an excipient.  [285] E128. A composition comprising 5‐chlorotryptammonium malate according to E122 as a first  component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.    [286] E129. A composition comprising crystalline 5‐chlorotryptammonium malate according to any  one of E123‐E125 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.  [287] E130. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ chlorotryptammonium malate according to E122.  [288] E131. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ chlorotryptammonium malate according to any one of E123‐E125.  [289] E132. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E126 or E128.  [290] E133. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E127 or E129.  [291] E134. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ chlorotryptammonium malate according to E122.  [292] E135. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ chlorotryptammonium malate according to any one of E123‐E125.  [293] E136. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E126 or E128.  [294] E137. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E127 or E129.  [295] E138. 2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐methoxy‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium).  [296] E139. Crystalline 2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐methoxy‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium).  [297] E140. Crystalline form 1 of 2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐methoxy‐ 1H‐indol‐3‐yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium).    [298] E141. Crystalline form 1 of 5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium according to E140, characterized by at least one of:    a triclinic crystal system at a temperature of about 300 K;    a P1 ത  space group at a temperature of about 300 K;    unit cell dimensions a = 9.5838(10) Å, b = 10.9915(12) Å, c = 12.6894(11) Å, α = 87.708(3)°, β  = 71.246(3)°, and ɣ = 84.805(4)°;    an X‐ray powder diffraction pattern substantially similar to FIG. 39; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 7.4,  18.4, and 19.6 °2θ ± 0.2 °2θ.  [299] E142. A composition comprising 5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium according to E138 and an excipient.  [300] E143. A composition comprising crystalline 5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium according to any one of E139‐E141 and an excipient.  [301] E144. A composition comprising 5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium according to E138 as a first component and a second component selected  from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified  cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a  monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.  [302] E145. A composition comprising crystalline 5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium according to any one of E139‐E141 as a first component and a second  component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative,  (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g)  a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.  [303] E146. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium according to E138.  [304] E147. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium according to any one of E139‐E141.  [305] E148. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E142 and E144.  [306] E149. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E143 and E145.  [307] E150. A method of preventing or treating inflammation and/or pain comprising the step of:      administering to a subject in need thereof a therapeutically effective amount of 5‐ methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium according to E138.  [308] E151. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium according to any one of E139‐E141.  [309] E152. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E142 or E144.  [310] E153. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E143 or E145.  [311] E154. Crystalline 2‐(5‐methyl‐1H‐indol‐3‐yl)ethan‐1‐amine (5‐methyltryptamine).  [312] E155. Crystalline form 1 of 2‐(5‐methyl‐1H‐indol‐3‐yl)ethan‐1‐amine (5‐methyltryptamine).  [313] E156. Crystalline form 1 of 5‐methyltryptamine according to E155, characterized by at least  one of:    an orthorhombic crystal system at a temperature of about 300 K;    a Pbca space group at a temperature of about 300 K;    unit cell dimensions a = 9.1099(11) Å, b = 11.3907(11) Å, c = 19.154(2) Å, α = 90°, β = 90°,  and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 40; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 13.4,  15.5, and 19.5 °2θ ± 0.2 °2θ.  [314] E157. A composition comprising crystalline 5‐methyltryptamine according to any one of 154‐ E156 and an excipient.  [315] E158. A composition comprising crystalline 5‐methyltryptamine according to any one of  E154‐E156 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.  [316] E159. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ methyltryptamine according to any one of E154‐E156.  [317] E160. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E157 or E158.  [318] E161. A method of preventing or treating inflammation and/or pain comprising the step of:      administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ methyltryptamine according to any one of E154‐E156.  [319] E162. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E157 or E158.  [320] E163. Crystalline bis(N‐[2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]‐N‐methylcyclopropanaminium)  (2E)‐but‐2‐enedioate (4‐hydroxy‐N‐methyl‐N‐cyclopropyltryptammonium fumarate).  [321] E164. Crystalline form 1 of bis(N‐[2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]‐N‐ methylcyclopropanaminium) (2E)‐but‐2‐enedioate (4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate).  [322] E165. Crystalline form 1 of 4‐hydroxy‐N‐methyl‐N‐cyclopropyltryptammonium fumarate  according to E164, characterized by at least one of:    a monoclinic crystal system at a temperature of about 300 K;    a C2/c space group at a temperature of about 300 K;    unit cell dimensions a = 19.5453(17) Å, b = 9.3265(7) Å, c = 17.4448(16) Å, α = 90°, β =  109.390(3)°, and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 41; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 9.6,  10.7, and 16.6 °2θ ± 0.2 °2θ.  [323] E166. A composition comprising crystalline 4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate according to any one of E163‐E165 and an excipient.  [324] E167. A composition comprising crystalline 4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate according to any one of E163‐E165 as a first component and a  second component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin  derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a  dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified  hericenone.  [325] E168. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 4‐ hydroxy‐N‐methyl‐N‐cyclopropyltryptammonium fumarate according to any one of E163‐E165.  [326] E169. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E166 or E167.  [327] E170. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 4‐ hydroxy‐N‐methyl‐N‐cyclopropyltryptammonium fumarate according to any one of E163‐E165.    [328] E171. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E166 or E167.  [329] E172. Crystalline [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]bis(propan‐2‐yl)azanium (2E)‐3‐ carboxyprop‐2‐enoate (4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate).  [330] E173. Crystalline form 1 of [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]bis(propan‐2‐yl)azanium (2E)‐3‐ carboxyprop‐2‐enoate (4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate).  [331] E174. Crystalline form 1 of 4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate  according to E173, characterized by at least one of:    an orthorhombic crystal system at a temperature of about 300 K;    a P212121space group at a temperature of about 300 K;    unit cell dimensions a = 7.9541(3) Å, b = 12.5763(5) Å, c = 20.3351(6) Å, α = 90°, β = 90°, and  ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 42; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 8.3,  11.2, and 15.8 °2θ ± 0.2 °2θ.  [332] E175. A composition comprising crystalline 4‐hydroxy‐N,N‐diisopropyltryptammonium  hydrofumarate according to any one of E172‐E174 and an excipient.  [333] E176. A composition comprising crystalline 4‐hydroxy‐N,N‐diisopropyltryptammonium  hydrofumarate according to any one of E172‐E174 as a first component and a second component  selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified  cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a  monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.  [334] E177. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 4‐ hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate according to any one of E172‐E174.  [335] E178. A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to E175 or E176.  [336] E179. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 4‐ hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate according to any one of E172‐E174.  [337] E180. A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to E175 or E176.  Examples  [338] The preparation and characterization of each of crystalline form 1 of bis(2‐(5‐methoxy‐1H‐   indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐enedioate (5‐methoxytryptammonium fumarate or 5‐MeO‐T  fumarate), crystalline form 1 of 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate  (tryptammonium hydromalate), crystalline form 1 of 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐ carboxybenzoate (tryptammonium hydrophthalate), crystalline form 1 of bis([2‐(4‐methoxy‐1H‐ indol‐3‐yl)ethyl](methyl)(propan‐2‐yl)azanium) (2E)‐but‐2‐enedioate (4‐methoxy‐N‐methyl‐N‐ isopropyltryptammonium fumarate or 4‐MeO‐MiPT fumarate), crystalline form 1 of [2‐(4‐hydroxy‐ 1H‐indol‐3‐yl)ethyl](propan‐2‐yl)propylazanium (2E)‐3‐carboxyprop‐2‐enoate (4‐hydroxy‐N‐propyl‐ N‐isopropyltryptammnonium hydrofumarate or 4‐HO‐PiPT hydrofumarate), crystalline form 1 of 2‐ (5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐chloro‐1H‐indol‐3‐yl)ethyl]azaniumyl}butanedioate  (5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium or 5‐Cl‐T∙N‐Suc‐5‐Cl‐T), crystalline  form 1 of 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate (5‐ chlorotryptammonium hydromaleate or 5‐Cl‐T hydromaleate), crystalline form 1 of 2‐(5‐chloro‐1H‐ indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (5‐chlorotryptammonium hydrophthalate or 5‐Cl‐T  hydrophthalate), crystalline form 1 of bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium) 2‐ hydroxybutanedioate (5‐chlorotryptammonium malate or 5‐Cl‐T malate), crystalline form 1 of 2‐(5‐ methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐methoxy‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium  or 5‐MeO‐T∙N‐Suc‐5‐MeO‐T), crystalline form 1 of 2‐(5‐methyl‐1H‐indol‐3‐yl)ethan‐1‐amine (5‐ methyltryptamine or 5‐Me‐T), crystalline form 1 of bis(N‐[2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]‐N‐ methylcyclopropanaminium) (2E)‐but‐2‐enedioate (4‐hydroxy‐N‐methyl‐N‐ cyclopropyltryptammonium fumarate or 4‐HO‐MCPT fumarate), and crystalline form 1 of [2‐(4‐ hydroxy‐1H‐indol‐3‐yl)ethyl]bis(propan‐2‐yl)azanium (2E)‐3‐carboxyprop‐2‐enoate (4‐hydroxy‐N,N‐ diisopropyltryptammonium hydrofumarate 4‐HO‐DiPT hydrofumarate) are described below.   [339] Single Crystal X‐Ray Diffraction (SCXRD) Characterization: Data were collected on a Bruker  D8 Venture CMOS Diffractometer equipped with an Oxford Cryosystems Cryostream cooling device  and using Mo Kα radiation. Structures were solved using the Bruker SHELXTL program and refined  with the SHELXTL program as part of the Bruker SHELXTL suite, or OLEX2 software. Unless otherwise  stated, hydrogen atoms attached to carbon were placed geometrically and allowed to refine with a  riding isotropic displacement parameter. Hydrogen atoms attached to a heteroatom were located in  a difference Fourier synthesis and were allowed to refine freely with an isotropic displacement  parameter.  [340] Preparation and Characterization of Crystalline form 1 of 5‐MeO‐T fumarate    [341] Synthesis  [342] 100 mg of 5‐methoxytryptamine freebase and 61 mg of fumaric acid were dissolved in 15 mL  of methanol. The solution was refluxed under nitrogen for 12 hours and solvent was removed in  vacuo. The residue was triturated with diethyl ether and filtered to yield the product as pale yellow  powder.  [343] Crystallization  [344] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  an acetone/water solution.  [345] Single Crystal Characterization  [346] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 5‐MeO‐T fumarate are reported in Table 3a, below. The data for crystalline form 1 of 5‐ MeO‐T fumarate in Table 3a relates to the asymmetric unit.  [347] Preparation and Characterization of Crystalline form 1 of tryptammonium hydromalate  [348] Synthesis  [349] 100 mg of tryptamine and 125 mg of DL‐malic acid were dissolved in 10 mL of methanol. The  solution was refluxed for 12 hours under an atmosphere of nitrogen. Solvent was removed in vacuo  to yield a tan oil that was recrystallized from acetone.  [350] Crystallization  [351] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  an aqueous solution.  [352] Single Crystal Characterization  [353] The single crystal data and structure refinement parameters for the crystalline form 1  structure of tryptammonium hydromalate are reported in Table 3a, below.   [354] Preparation and Characterization of Crystalline form 1 of tryptammonium hydrophthalate  [355] Synthesis  [356] 150 mg of tryptamine and 155 mg of phthalic acid were dissolved in 10 mL of methanol. The  solution was refluxed for 12 hours under an atmosphere of nitrogen. Solvent was removed in vacuo  to yield a brown oil that solidified to yield the hydrophthalate salt.  [357] Crystallization  [358] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  a methanol solution.    [359] Single Crystal Characterization  [360] The single crystal data and structure refinement parameters for the crystalline form 1  structure of tryptammonium hydrophthalate are reported in Table 3a, below.   [361] Preparation and Characterization of Crystalline form 1 of 4‐MeO‐MiPT fumarate  [362] Synthesis  [363] 100 mg of 4‐methoxy‐N‐methyl‐N‐isopropyltryptamine hydrofumarate and 104 mg of lead  (II) acetate were dissolved in 15 mL of distilled water and allowed to stir for one hour. The resulting  white precipitate (lead fumarate) was removed via filtration and the solvent of the filtrate was  removed in vacuo. The resulting residue was picked up in acetone and filtered again. Solvent was  removed in vacuo to yield a yellow oil which was recrystallized from acetone.  [364] Crystallization  [365] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  an acetone solution.  [366] Single Crystal Characterization  [367] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 4‐MeO‐MiPT fumarate are reported in Table 3a, below. The data for crystalline form 1 of  4‐MeO‐MiPT fumarate in Table 3a relates to the asymmetric unit.  [368] Preparation and Characterization of Crystalline form 1 of 4‐HO‐PiPT hydrofumarate  [369] Crystallization  [370] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  an isopropanol/acetone solution of a commercial sample (ChemLogix).  [371] Single Crystal Characterization  [372] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 4‐HO‐PiPT hydrofumarate are reported in Table 3a, below.   [373] Preparation and Characterization of Crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T  [374] Synthesis  [375] 76 mg of freebase 5‐chlorotryptamine and 23 mg of maleic acid were mixed together in  methanol and heated at reflux for 48 hours. Solvent was removed in vacuo to yield solid product.  [376] Crystallization  [377] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  an acetone solution.    [378] Single Crystal Characterization  [379] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T are reported in Table 3a, below.   [380] Preparation and Characterization of Crystalline form 1 of 5‐Cl‐T hydromaleate  [381] Synthesis  [382] 75 mg of 5‐chlorotryptamine and 45 mg of maleic acid were dissolved in 15 mL of methanol.  The solution was heated at reflux for 24 hours. Solvent was removed in vacuo to yield a solid which  was recrystallized from methanol.  [383] Crystallization  [384] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  a methanol solution.  [385] Single Crystal Characterization  [386] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 5‐Cl‐T hydromaleate are reported in Table 3a, below.   [387] Preparation and Characterization of Crystalline form 1 of 5‐Cl‐T hydrophthalate  [388] Synthesis  [389] 82 mg of 5‐chlorotryptamine and 70 mg of phthalic acid were dissolved in 15 mL of  methanol. The solution was heated at reflux for 48 hours. Solvent was removed in vacuo to yield the  product as a powder.  [390] Crystallization  [391] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  a methanol solution.  [392] Single Crystal Characterization  [393] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 5‐Cl‐T hydrophthalate are reported in Table 3b, below.   [394] Preparation and Characterization of Crystalline form 1 of 5‐Cl‐T malate  [395] Synthesis  [396] 93 mg of 5‐chlorotryptamine and 32 mg of DL‐malic acid were dissolved in 20 mL of  methanol. The solution was refluxed for 24 hours. Solvent was removed in vacuo to yield a  crystalline solid.  [397] Crystallization  [398] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  a methanol solution.    [399] Single Crystal Characterization  [400] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 5‐Cl‐T malate are reported in Table 3b, below.   [401] Preparation and Characterization of Crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T  [402] Synthesis  [403] 87 mg of 5‐methoxytryptamine freebase was mixed with 26 mg of maleic acid in methanol.  The solution was heated at reflux for 48 hours. Solvent was removed in vacuo to yield a solid.  [404] Crystallization  [405] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  an acetone/water solution.  [406] Single Crystal Characterization  [407] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T are reported in Table 3b, below.   [408] Preparation and Characterization of Crystalline form 1 of 5‐Me‐T  [409] Synthesis  [410] 506 mg of 5‐methyltryptamine hydrochloride was dissolved in 35 mL of dichloromethane.  193 mg of sodium hydroxide was dissolved in 35 mL of distilled water and this was added to the first  solution. The biphasic mixture was stirred for two hours. The organic layer was isolated, washed four  times, and dried over sodium sulfate. Solvent was removed in vacuo to yield the freebase.  [411] Crystallization  [412] Single crystals suitable for X‐ray diffraction studies were grown from the slow evaporation of  a dichloromethane solution.  [413] Single Crystal Characterization  [414] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 5‐Me‐T are reported in Table 3b, below.   [415] Preparation and Characterization of Crystalline form 1 of 4‐HO‐MCPT fumarate  [416] Crystallization  [417] Crystals suitable for single crystal X‐ray diffraction studies were grown from the slow  evaporation of a commercial sample (The Indole Shop).  [418] Single Crystal Characterization  [419] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 4‐HO‐MCPT fumarate are reported in Table 3b, below. The data for crystalline form 1 of  4‐HO‐MCPT fumarate in Table 3b relates to the asymmetric unit.    [420] Preparation and Characterization of Crystalline form 1 of 4‐HO‐DiPT hydrofumarate  [421] Crystallization  [422] Crystals suitable for single crystal X‐ray analysis were grown from the slow evaporation of a  methanol/water solution of a commercial sample from ChemLogix (Burnaby, BC Canada).  [423] Single Crystal Characterization  [424] The single crystal data and structure refinement parameters for the crystalline form 1  structure of 4‐HO‐DiPT hydrofumarate are reported in Table 3b, below.   Table 3a 
Figure imgf000101_0001
 
Figure imgf000102_0001
 
Figure imgf000103_0001
 
Figure imgf000104_0001
 
Figure imgf000105_0001
  Table 3b 
Figure imgf000105_0002
 
Figure imgf000106_0001
 
Figure imgf000107_0001
 
Figure imgf000108_0001
  [425] FIG. 1 shows the molecular structure of crystalline form 1 of 5‐MeO‐T fumarate, showing the  atomic labeling.   [426] FIG. 2 shows the molecular structure of crystalline form 1 of tryptammonium hydromalate,  showing the atomic labeling.   [427] FIG. 3 shows the molecular structure of crystalline form 1 of tryptammonium  hydrophthalate, showing the atomic labeling.   [428] FIG. 4 shows the molecular structure of crystalline form 1 of 4‐MeO‐MiPT fumarate, showing  the atomic labeling.   [429] FIG. 5 shows the molecular structure of crystalline form 1 of 4‐HO‐PiPT hydrofumarate,  showing the atomic labeling.   [430] FIG. 6 shows the molecular structure of crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T, showing the  atomic labeling.   [431] FIG. 7 shows the molecular structure of crystalline form 1 of 5‐Cl‐T hydromaleate, showing  the atomic labeling.   [432] FIG. 8 shows the molecular structure of crystalline form 1 of 5‐Cl‐T hydrophthalate, showing  the atomic labeling.   [433] FIG. 9 shows the molecular structure of crystalline form 1 of 5‐Cl‐T malate, showing the  atomic labeling.   [434] FIG. 10 shows the molecular structure of crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T,  showing the atomic labeling.   [435] FIG. 11 shows the molecular structure of crystalline form 1 of 5‐Me‐T, showing the atomic  labeling.     [436] FIG. 12 shows the molecular structure of crystalline form 1 of 4‐HO‐MCPT fumarate, showing  the atomic labeling.   [437] FIG. 13 shows the molecular structure of crystalline form 1 of 4‐HO‐DiPT hydrofumarate,  showing the atomic labeling.   [438] FIG. 14 shows the unit cell of crystalline form 1 of 5‐MeO‐T fumarate along the a‐axis.  [439] FIG. 15 shows the unit cell of crystalline form 1 of tryptammonium hydromalate along the a‐ axis.  [440] FIG. 16 shows the unit cell of crystalline form 1 of tryptammonium hydrophthalate along the  b‐axis.  [441] FIG. 17 shows the unit cell of crystalline form 1 of 4‐MeO‐MiPT fumarate along the c‐axis.  [442] FIG. 18 shows the unit cell of crystalline form 1 of 4‐HO‐PiPT hydrofumarate along the a‐axis.  [443] FIG. 19 shows the unit cell of crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T along the a‐axis.  [444] FIG. 20 shows the unit cell of crystalline form 1 of 5‐Cl‐T hydromaleate along the b‐axis.  [445] FIG. 21 shows the unit cell of crystalline form 1 of 5‐Cl‐T hydrophthalate along the c‐axis.  [446] FIG. 22 shows the unit cell of crystalline form 1 of 5‐Cl‐T malate along the a‐axis.  [447] FIG. 23 shows the unit cell of crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T along the a‐axis.  [448] FIG. 24 shows the unit cell of crystalline form 1 of 5‐Me‐T along the a‐axis.  [449] FIG. 25 shows the unit cell of crystalline form 1 of 4‐HO‐MCPT fumarate along the b‐axis.  [450] FIG. 26 shows the unit cell of crystalline form 1 of 4‐HO‐DiPT hydrofumarate along the a‐ axis.  [451] FIG. 27 shows the 2:1 ratio of crystalline form 1 of 5‐MeO‐T fumarate as a dimer.  [452] FIG. 28 shows the 2:1 ratio of crystalline form 1 of 4‐MeO‐MiPT fumarate as a dimer.  [453] FIG. 29 shows the 2:1 ratio of crystalline form 1 of 4‐HO‐MCPT fumarate as a dimer.  [454] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [455] FIG. 30 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐MeO‐T fumarate generated from its single crystal data. Table 4 lists the angles, °2θ ± 0.2°2θ, and  d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 30. The entire list of  peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the cocrystal  may be characterized by at least two peaks selected from the peaks at 7.3, 12.5, and 24.8 °2θ ±  0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to FIG. 30.  [456] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [457] FIG. 31 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  tryptammonium hydromalate generated from its single crystal data. Table 5 lists the angles, °2θ ±  0.2°2θ, and d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 31. The entire    list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the  cocrystal may be characterized by at least two peaks selected from the peaks at 7.1, 11.3, and 20.9  °2θ ± 0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to  FIG. 31.  [458] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [459] FIG. 32 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  tryptammonium hydrophthalate generated from its single crystal data. Table 6 lists the angles, °2θ ±  0.2°2θ, and d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 32. The entire  list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the  cocrystal may be characterized by at least two peaks selected from the peaks at 6.0, 11.2, and 15.4  °2θ ± 0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to  FIG. 32.  [460] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [461] FIG. 33 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  4‐MeO‐MiPT fumarate generated from its single crystal data. Table 7 lists the angles, °2θ ± 0.2°2θ,  and d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 33. The entire list of  peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the cocrystal  may be characterized by at least two peaks selected from the peaks at 9.1, 14.5, and 16.0 °2θ ±  0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to FIG. 33.  [462] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [463] FIG. 34 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  4‐HO‐PiPT hydrofumarate generated from its single crystal data. Table 8 lists the angles, °2θ ±  0.2°2θ, and d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 34. The entire  list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the  cocrystal may be characterized by at least two peaks selected from the peaks at 11.1, 12.0, and 15.8  °2θ ± 0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to  FIG. 34.  [464] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [465] FIG. 35 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐Cl‐T∙N‐Suc‐5‐Cl‐T generated from its single crystal data. Table 9 lists the angles, °2θ ± 0.2°2θ, and  d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 35. The entire list of  peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the cocrystal  may be characterized by at least two peaks selected from the peaks at 12.8, 15.9, and 22.9 °2θ ±  0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to FIG. 35.    [466] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [467] FIG. 36 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐Cl‐T hydromaleate generated from its single crystal data. Table 10 lists the angles, °2θ ± 0.2°2θ,  and d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 36. The entire list of  peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the cocrystal  may be characterized by at least two peaks selected from the peaks at 9.2, 10.6, and 14.8 °2θ ±  0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to FIG. 36.  [468] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [469] FIG. 37 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐Cl‐T hydrophthalate generated from its single crystal data. Table 11 lists the angles, °2θ ± 0.2°2θ,  and d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 37. The entire list of  peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the cocrystal  may be characterized by at least two peaks selected from the peaks at 11.3, 12.3, and 15.4 °2θ ±  0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to FIG. 37.  [470] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [471] FIG. 38 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐Cl‐T malate generated from its single crystal data. Table 12 lists the angles, °2θ ± 0.2°2θ, and d‐ spacing of the peaks identified in the experimental XRPD pattern of FIG. 38. The entire list of peaks,  or a subset thereof, may be sufficient to characterize the cocrystal. For example, the cocrystal may  be characterized by at least two peaks selected from the peaks at 12.5, 13.2, and 14.3 °2θ ± 0.2°2θ  or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to FIG. 38.  [472] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [473] FIG. 39 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐MeO‐T∙N‐Suc‐5‐MeO‐T generated from its single crystal data. Table 13 lists the angles, °2θ ±  0.2°2θ, and d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 39. The entire  list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the  cocrystal may be characterized by at least two peaks selected from the peaks at 7.4, 18.4, and 19.6  °2θ ± 0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to  FIG. 39.  [474] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [475] FIG. 40 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  5‐Me‐T generated from its single crystal data. Table 14 lists the angles, °2θ ± 0.2°2θ, and d‐spacing of  the peaks identified in the experimental XRPD pattern of FIG. 40. The entire list of peaks, or a subset  thereof, may be sufficient to characterize the cocrystal. For example, the cocrystal may be    characterized by at least two peaks selected from the peaks at 13.4, 15.5, and 19.5 °2θ ± 0.2°2θ or  their corresponding d‐spacing as well as by an XRPD pattern substantially similar to FIG. 40.  [476] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [477] FIG. 41 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  4‐HO‐MCPT fumarate generated from its single crystal data. Table 15 lists the angles, °2θ ± 0.2°2θ,  and d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 41. The entire list of  peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the cocrystal  may be characterized by at least two peaks selected from the peaks at 9.6, 10.7, and 16.6 °2θ ±  0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to FIG. 41.  [478] Simulated Powder X‐ray Diffraction (PXRD) Pattern  [479] FIG. 42 shows a simulated X‐ray powder diffraction pattern (XRPD) for crystalline form 1 of  4‐HO‐DiPT hydrofumarate generated from its single crystal data. Table 16 lists the angles, °2θ ±  0.2°2θ, and d‐spacing of the peaks identified in the experimental XRPD pattern of FIG. 42. The entire  list of peaks, or a subset thereof, may be sufficient to characterize the cocrystal. For example, the  cocrystal may be characterized by at least two peaks selected from the peaks at 8.3, 11.2, and 15.8  °2θ ± 0.2°2θ or their corresponding d‐spacing as well as by an XRPD pattern substantially similar to  FIG. 42.  Table 4: Crystalline form 1 of 5‐MeO‐T fumarate 
Figure imgf000112_0001
 
Figure imgf000113_0001
  Table 5: Crystalline form 1 of tryptammonium hydromalate 
Figure imgf000113_0002
 
Figure imgf000114_0001
  Table 6: Crystalline form 1 of tryptammonium hydrophthalate 
Figure imgf000114_0002
 
Figure imgf000115_0001
 
Figure imgf000116_0001
  Table 7: Crystalline form 1 of 4‐MeO‐MiPT fumarate 
Figure imgf000116_0002
 
Figure imgf000117_0001
  Table 8: Crystalline form 1 of 4‐HO‐PiPT hydrofumarate 
Figure imgf000117_0002
 
Figure imgf000118_0001
 
Figure imgf000119_0001
  Table 9: Crystalline form 1 of 5‐Cl‐T∙N‐Suc‐5‐Cl‐T 
Figure imgf000119_0002
 
Figure imgf000120_0001
 
Figure imgf000121_0001
  Table 10: Crystalline form 1 of 5‐Cl‐T hydromaleate 
Figure imgf000121_0002
 
Figure imgf000122_0001
  Table 11: Crystalline form 1 of 5‐Cl‐T hydrophthalate 
Figure imgf000122_0002
 
Figure imgf000123_0001
 
Figure imgf000124_0001
  Table 12: Crystalline form 1 of 5‐Cl‐T malate 
Figure imgf000124_0002
 
Figure imgf000125_0001
  Table 13: Crystalline form 1 of 5‐MeO‐T∙N‐Suc‐5‐MeO‐T 
Figure imgf000125_0002
 
Figure imgf000126_0001
 
Figure imgf000127_0001
 
Figure imgf000128_0001
  Table 14: Crystalline form 1 of 5‐Me‐T 
Figure imgf000128_0002
 
Figure imgf000129_0001
  Table 15: Crystalline form 1 of 4‐HO‐MCPT fumarate 
Figure imgf000129_0002
 
Figure imgf000130_0001
  Table 16: Crystalline form 1 of 4‐HO‐DiPT hydrofumarate 
Figure imgf000130_0002
 
Figure imgf000131_0001
    References  Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst.  42, 339–341.  Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.       

Claims

  The claimed invention is:    1.  Bis(2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐enedioate (5‐ methoxytryptammonium fumarate).    2.  Crystalline bis(2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐enedioate (5‐ methoxytryptammonium fumarate).    3.  Crystalline form 1 of bis(2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium) (2E)‐but‐2‐enedioate (5‐ methoxytryptammonium fumarate).    4.  Crystalline form 1 of 5‐methoxytryptammonium fumarate according to claim 3, characterized  by at least one of:    a monoclinic crystal system at a temperature of about 297 K;    a P21/c  space group at a temperature of about 297 K;    unit cell dimensions a = 5.8070(3) Å, b = 24.2768(13) Å, c = 8.9334(5) Å, α = 90°, β = 103.360(2)°,  and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 30; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 7.3, 12.5,  and 24.8 °2θ ± 0.2 °2θ.    5.  A composition comprising 5‐methoxytryptammonium fumarate according to claim 1 and an  excipient.    6.  A composition comprising crystalline 5‐methoxytryptammonium fumarate according to any one  of claims 2‐4 and an excipient.    7.  A composition comprising 5‐methoxytryptammonium fumarate according to claim 1 as a first  component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.      8.  A composition comprising crystalline 5‐methoxytryptammonium fumarate according to any one  of claims 2‐4 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    9.  A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ methoxytryptammonium fumarate according to claim 1.    10.  A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ methoxytryptammonium fumarate according to any one of claims 2‐4.    11.  A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to claim 5.    12.  A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to claim 7.    13.  A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to claim 6.    14.  A method of preventing or treating a psychological disorder comprising the step of:    administering to a subject in need thereof a composition according to claim 8.    15.  A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of 5‐ methoxytryptammonium fumarate according to claim 1.    16.  A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a therapeutically effective amount of crystalline 5‐ methoxytryptammonium fumarate according to any one of claims 2‐4.      17.  A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to claim 5.    18.  A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to claim 7.    19.  A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to claim 6.    20.   A method of preventing or treating inflammation and/or pain comprising the step of:    administering to a subject in need thereof a composition according to claim 8.    21.  2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate (tryptammonium  hydromalate).    22.  Crystalline 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate (tryptammonium  hydromalate).    23.  Crystalline form 1 of 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate  (tryptammonium hydromalate).    24.  Crystalline form 1 of tryptammonium hydromalate according to claim 23, characterized by at  least one of:    an orthorhombic crystal system at a temperature of about 297 K;    a P212121 space group at a temperature of about 297 K;    unit cell dimensions a = 7.2012(5) Å, b = 8.2509(5) Å, c = 24.7541(16) Å, α = 90°, β = 90°, and ɣ =  90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 31; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 7.1, 11.3,  and 20.9 °2θ ± 0.2 °2θ.    25.  A composition comprising tryptammonium hydromalate according to claim 21 and an excipient.      26.  A composition comprising crystalline tryptammonium hydromalate according to any one of  claims 22‐24 and an excipient.    27.  A composition comprising tryptammonium hydromalate according to claim 21 as a first  component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.    28.  A composition comprising crystalline tryptammonium hydromalate according to any one of  claims 22‐24 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    29.  2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (tryptammonium hydrophthalate).    30.  Crystalline 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (tryptammonium  hydrophthalate).    31.  Crystalline form 1 of 2‐(1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (tryptammonium  hydrophthalate).    32.  Crystalline form 1 of tryptammonium hydrophthalate according to claim 31, characterized by at  least one of:    a monoclinic crystal system at a temperature of about 297 K;    a C2/c space group at a temperature of about 297 K;    unit cell dimensions a = 18.7823(11) Å, b = 5.7731(3) Å, c = 29.3825(19) Å, α = 90°, β =  90.617(2)°, and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 32; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 6.0, 11.2,  and 15.4 °2θ ± 0.2 °2θ.      33.  A composition comprising tryptammonium hydrophthalate according to claim 29 and an  excipient.    34.  A composition comprising crystalline tryptammonium hydrophthalate according to any one of  claims 30‐32 and an excipient.    35.  A composition comprising tryptammonium hydrophthalate according to claim 29 as a first  component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.    36.  A composition comprising crystalline tryptammonium hydrophthalate according to any one of  claims 30‐32as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    37.  Bis([2‐(4‐methoxy‐1H‐indol‐3‐yl)ethyl](methyl)(propan‐2‐yl)azanium) (2E)‐but‐2‐enedioate (4‐ methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate).    38.  Crystalline bis([2‐(4‐methoxy‐1H‐indol‐3‐yl)ethyl](methyl)(propan‐2‐yl)azanium) (2E)‐but‐2‐ enedioate (4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate).    39.  Crystalline form 1 of bis([2‐(4‐methoxy‐1H‐indol‐3‐yl)ethyl](methyl)(propan‐2‐yl)azanium) (2E)‐ but‐2‐enedioate (4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate).    40.  Crystalline form 1 of 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate according to  claim 39, characterized by at least one of:    a monoclinic crystal system at a temperature of about 297 K;    a P21/n space group at a temperature of about 297 K;    unit cell dimensions a = 9.1438(3) Å, b = 13.8957(6) Å, c = 13.6658(6) Å, α = 90°, β =  94.6140(10)°, and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 33; or      an X‐ray powder diffraction pattern characterized by at least two peaks selected from 9.1, 14.5,  and 16.0 °2θ ± 0.2 °2θ.    41.  A composition comprising 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate  according to claim 37 and an excipient.    42.  A composition comprising crystalline 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium  fumarate according to any one of claims 38‐40 and an excipient.    43.  A composition comprising 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium fumarate  according to claim 37 as a first component and a second component selected from at least one of (a)  a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    44.  A composition comprising crystalline 4‐methoxy‐N‐methyl‐N‐isopropyltryptammonium  fumarate according to any one of claims 38‐40 as a first component and a second component  selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified  cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a  monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.    45.  Crystalline [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl](propan‐2‐yl)propylazanium (2E)‐3‐carboxyprop‐2‐ enoate (4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate).    46.  Crystalline form 1 of [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl](propan‐2‐yl)propylazanium (2E)‐3‐ carboxyprop‐2‐enoate (4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate).    47.  Crystalline form 1 of 4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium hydrofumarate according  to claim 46, characterized by at least one of:    an orthorhombic crystal system at a temperature of about 297 K;    a P212121 space group at a temperature of about 297 K;    unit cell dimensions a = 7.8854(7) Å, b = 12.7401(11) Å, c = 20.5577(18) Å, α = 90°, β = 90°, and ɣ  = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 34; or      an X‐ray powder diffraction pattern characterized by at least two peaks selected from 11.1,  12.0, and 15.8 °2θ ± 0.2 °2θ.    48.  A composition comprising crystalline 4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium  hydrofumarate according to any one of claims 45‐47 and an excipient.    49.  A composition comprising crystalline 4‐hyroxy‐N‐propyl‐N‐isopropyltryptammnonium  hydrofumarate according to any one of claims 45‐47 as a first component and a second component  selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified  cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a  monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.    50.  2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐chloro‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium).    51.  Crystalline 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐chloro‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium).    52.  Crystalline form 1 of 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐chloro‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium).    53.  Crystalline form 1 of 5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium according to  claim 52, characterized by at least one of:    a triclinic crystal system at a temperature of about 300 K;    a P1 ത  space group at a temperature of about 300 K;    unit cell dimensions a = 9.5806(13) Å, b = 11.1666(14) Å, c = 11.5518(17) Å, α = 87.333(5)°, β =  74.347(5)°, and ɣ = 85.637(5)°;    an X‐ray powder diffraction pattern substantially similar to FIG. 35; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 12.8,  15.9, and 22.9 °2θ ± 0.2 °2θ.    54.  A composition comprising 5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium  according to claim 50 and an excipient.      55.  A composition comprising crystalline 5‐chlorotryptammonium N‐succinyl‐5‐ chlorotryptammonium according to any one of claims 51‐53 and an excipient.    56.  A composition comprising 5‐chlorotryptammonium N‐succinyl‐5‐chlorotryptammonium  according to claim 50 as a first component and a second component selected from at least one of (a)  a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    57.  A composition comprising crystalline 5‐chlorotryptammonium N‐succinyl‐5‐ chlorotryptammonium according to any one of claims 51‐53 as a first component and a second  component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative,  (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g)  a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.    58.  2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate (5‐ chlorotryptammonium hydromaleate).    59.  Crystalline 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐hydroxypropanoate (5‐ chlorotryptammonium hydromaleate).    60.  Crystalline form 1 of 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 3‐carboxy‐2‐ hydroxypropanoate (5‐chlorotryptammonium hydromaleate).    61.  Crystalline form 1 of 5‐chlorotryptammonium hydromaleate according to claim 60,  characterized by at least one of:    a monoclinic crystal system at a temperature of about 300 K;    a P21/c space group at a temperature of about 300 K;    unit cell dimensions a = 9.6320(7) Å, b = 5.4224(4) Å, c = 28.494(2) Å, α = 90°, β = 95.758(3)°,  and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 36; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 9.2, 10.6,  and 14.8 °2θ ± 0.2 °2θ.      62.  A composition comprising 5‐chlorotryptammonium hydromaleate according to claim 58 and an  excipient.    63.  A composition comprising crystalline 5‐chlorotryptammonium hydromaleate according to any  one of claims 59‐61 and an excipient.    64.  A composition comprising 5‐chlorotryptammonium hydromaleate according to claim 58 as a  first component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.    65.  A composition comprising crystalline 5‐chlorotryptammonium hydromaleate according to any  one of claims 59‐61as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    66.  2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (5‐chlorotryptammonium  hydrophthalate).    67.  Crystalline 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (5‐ chlorotryptammonium hydrophthalate).    68.  Crystalline form 1 of 2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐carboxybenzoate (5‐ chlorotryptammonium hydrophthalate).    69.  Crystalline form 1 of 5‐chlorotryptammonium hydrophthalate according to claim 68,  characterized by at least one of:    a triclinic crystal system at a temperature of about 300 K;    a P1 ത   space group at a temperature of about 300 K;    unit cell dimensions a = 7.4013(6) Å, b = 9.8217(9) Å, c = 12.1614(12) Å, α = 83.285(3)°, β =  79.601(3)°, and ɣ = 78.437(3)°;    an X‐ray powder diffraction pattern substantially similar to FIG. 37; or      an X‐ray powder diffraction pattern characterized by at least two peaks selected from 11.3,  12.3, and 15.4 °2θ ± 0.2 °2θ.    70.  A composition comprising 5‐chlorotryptammonium hydrophthalate according to claim 66 and  an excipient.    71.  A composition comprising crystalline 5‐chlorotryptammonium hydrophthalate according to any  one of claims 67‐69 and an excipient.    72.  A composition comprising 5‐chlorotryptammonium hydrophthalate according to claim 66 as a  first component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.    73.  A composition comprising crystalline 5‐chlorotryptammonium hydrophthalate according to any  one of claims 67‐69  as a first component and a second component selected from at least one of (a)  a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    74.  Bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium) 2‐hydroxybutanedioate (5‐ chlorotryptammonium malate).    75.  Crystalline bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium) 2‐hydroxybutanedioate (5‐ chlorotryptammonium malate).    76.  Crystalline form 1 of bis(2‐(5‐chloro‐1H‐indol‐3‐yl)ethan‐1‐aminium) 2‐hydroxybutanedioate (5‐ chlorotryptammonium malate).    77.  Crystalline form 1 of 5‐chlorotryptammonium malate according to claim 76, characterized by at  least one of:    a monoclinic crystal system at a temperature of about 300 K;    a P21 space group at a temperature of about 300 K;      unit cell dimensions a = 8.9975(8) Å, b = 12.3798(12) Å, c = 11.3628(11) Å, α = 90°, β =  106.617(3)°, and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 38; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 12.5,  13.2, and 14.3 °2θ ± 0.2 °2θ.    78.  A composition comprising 5‐chlorotryptammonium malate according to claim 74 and an  excipient.    79.  A composition comprising crystalline 5‐chlorotryptammonium malate according to any one of  claims 75‐77 and an excipient.    80.  A composition comprising 5‐chlorotryptammonium malate according to claim 74 as a first  component and a second component selected from at least one of (a) a serotonergic drug, (b) a  purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic  drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a  purified hericenone.    81.  A composition comprising crystalline 5‐chlorotryptammonium malate according to any one of  claims 75‐77 as a first component and a second component selected from at least one of (a) a  serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    82.  2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐methoxy‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium).    83.  Crystalline 2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐methoxy‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium).      84.  Crystalline form 1 of 2‐(5‐methoxy‐1H‐indol‐3‐yl)ethan‐1‐aminium 2‐{[2‐(5‐methoxy‐1H‐indol‐3‐ yl)ethyl]azaniumyl}butanedioate (5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium).    85.  Crystalline form 1 of 5‐methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium  according to claim 84, characterized by at least one of:    a triclinic crystal system at a temperature of about 300(2) K;    a P1 ത  space group at a temperature of about 300(2) K;    unit cell dimensions a = 9.5838(10) Å, b = 10.9915(12) Å, c = 12.6894(11) Å, α = 87.708(3)°, β =  71.246(3)°, and ɣ = 84.805(4)°;    an X‐ray powder diffraction pattern substantially similar to FIG. 39; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 7.4, 18.4,  and 19.6 °2θ ± 0.2 °2θ.    86.  A composition comprising 5‐methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium  according to claim 82 and an excipient.    87.  A composition comprising crystalline 5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium according to any one of claims 83‐85 and an excipient.    88.  A composition comprising 5‐methoxytryptammonium N‐succinyl‐5‐methoxytryptammonium  according to claim 82 as a first component and a second component selected from at least one of (a)  a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified  terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a  purified erinacine, and (i) a purified hericenone.    89.  A composition comprising crystalline 5‐methoxytryptammonium N‐succinyl‐5‐ methoxytryptammonium according to any one of claims 83‐85 as a first component and a second  component selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative,  (c) a purified cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g)  a monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.    90.  Crystalline 2‐(5‐methyl‐1H‐indol‐3‐yl)ethan‐1‐amine (5‐methyltryptamine).      91.  Crystalline form 1 of 2‐(5‐methyl‐1H‐indol‐3‐yl)ethan‐1‐amine (5‐methyltryptamine).    92.  Crystalline form 1 of 5‐methyltryptamine according to claim 91, characterized by at least one of:    an orthorhombic crystal system at a temperature of about 300 K;    a Pbca space group at a temperature of about 300 K;    unit cell dimensions a = 9.1099(11) Å, b = 11.3907(11) Å, c = 19.154(2) Å, α = 90°, β = 90°, and ɣ  = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 40; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 13.4,  15.5, and 19.5 °2θ ± 0.2 °2θ.    93.  A composition comprising crystalline 5‐methyltryptamine according to any one of claims 90‐92  and an excipient.    94.  A composition comprising crystalline 5‐methyltryptamine according to any one of claims 90‐ 92as a first component and a second component selected from at least one of (a) a serotonergic  drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid, (d) a purified terpene, (e) an  adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase inhibitor, (h) a purified erinacine,  and (i) a purified hericenone.    95.  Crystalline bis(N‐[2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]‐N‐methylcyclopropanaminium) (2E)‐but‐2‐ enedioate (4‐hydroxy‐N‐methyl‐N‐cyclopropyltryptammonium fumarate).    96.  Crystalline form 1 of bis(N‐[2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]‐N‐methylcyclopropanaminium)  (2E)‐but‐2‐enedioate (4‐hydroxy‐N‐methyl‐N‐cyclopropyltryptammonium fumarate).    97.  Crystalline form 1 of 4‐hydroxy‐N‐methyl‐N‐cyclopropyltryptammonium fumarate according to  claim 96, characterized by at least one of:    a monoclinic crystal system at a temperature of about 300 K;    a C2/c space group at a temperature of about 300 K;    unit cell dimensions a = 19.5453(17) Å, b = 9.3265(7) Å, c = 17.4448(16) Å, α = 90°, β =  109.390(3)°, and ɣ = 90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 41; or      an X‐ray powder diffraction pattern characterized by at least two peaks selected from 9.6, 10.7,  and 16.6 °2θ ± 0.2 °2θ.    98.  A composition comprising crystalline 4‐hydroxy‐N‐methyl‐N‐cyclopropyltryptammonium  fumarate according to any one of claims 95‐97 and an excipient.    99.  A composition comprising crystalline 4‐hydroxy‐N‐methyl‐N‐cyclopropyltryptammonium  fumarate according to any one of claims 95‐97  as a first component and a second component  selected from at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified  cannabinoid, (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a  monoamine oxidase inhibitor, (h) a purified erinacine, and (i) a purified hericenone.    100. Crystalline [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]bis(propan‐2‐yl)azanium (2E)‐3‐carboxyprop‐2‐ enoate (4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate).    101. Crystalline form 1 of [2‐(4‐hydroxy‐1H‐indol‐3‐yl)ethyl]bis(propan‐2‐yl)azanium (2E)‐3‐ carboxyprop‐2‐enoate (4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate).    102. Crystalline form 1 of 4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate according to  claim 101, characterized by at least one of:    an orthorhombic crystal system at a temperature of about 300 K;    a P212121space group at a temperature of about 300 K;    unit cell dimensions a = 7.9541(3) Å, b = 12.5763(5) Å, c = 20.3351(6) Å, α = 90°, β = 90°, and ɣ =  90°;    an X‐ray powder diffraction pattern substantially similar to FIG. 42; or    an X‐ray powder diffraction pattern characterized by at least two peaks selected from 8.3, 11.2,  and 15.8 °2θ ± 0.2 °2θ.    103. A composition comprising crystalline 4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate  according to any one of claims 100‐102 and an excipient.    104. A composition comprising crystalline 4‐hydroxy‐N,N‐diisopropyltryptammonium hydrofumarate  according to any one of claims 100‐102 as a first component and a second component selected from  at least one of (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) a purified cannabinoid,    (d) a purified terpene, (e) an adrenergic drug, (f) a dopaminergic drug, (g) a monoamine oxidase  inhibitor, (h) a purified erinacine, and (i) a purified hericenone.     
PCT/US2023/081591 2022-11-29 2023-11-29 Tryptamine derivatives Ceased WO2024118767A2 (en)

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WO2024227149A3 (en) * 2023-04-27 2025-02-06 Atai Therapeutics, Inc. Alkoxy and carbamoyl quaternary amine salts as prodrugs of trpytamines
WO2025042937A1 (en) * 2023-08-22 2025-02-27 Caamtech, Inc. 5-methoxytryptammonium hydrophthalate
WO2025043053A1 (en) * 2023-08-23 2025-02-27 Caamtech, Inc. 4-methoxy-n,n-dicyclopropyltryptammonium chloride
US12378194B2 (en) 2021-05-25 2025-08-05 Atai Therapeutics, Inc. N, n-dimethyltryptamine salts and crystalline salt forms
US12396982B2 (en) 2020-05-08 2025-08-26 Atai Therapeutics, Inc. Compositions of matter and pharmaceutical compositions

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WO2020181194A1 (en) * 2019-03-07 2020-09-10 University Of Padova Compositions and methods of use comprising substances with neural plasticity actions administered at non-psychedelic/psychotomimetic dosages and formulations
AU2020386445A1 (en) * 2019-11-19 2022-06-02 Paul Edward Stamets Tryptamine compositions for enhancing neurite outgrowth

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US12396982B2 (en) 2020-05-08 2025-08-26 Atai Therapeutics, Inc. Compositions of matter and pharmaceutical compositions
US12472163B2 (en) 2020-05-08 2025-11-18 Atai Therapeutics, Inc. Compositions of matter and pharmaceutical compositions
US12378194B2 (en) 2021-05-25 2025-08-05 Atai Therapeutics, Inc. N, n-dimethyltryptamine salts and crystalline salt forms
WO2024227149A3 (en) * 2023-04-27 2025-02-06 Atai Therapeutics, Inc. Alkoxy and carbamoyl quaternary amine salts as prodrugs of trpytamines
WO2025042937A1 (en) * 2023-08-22 2025-02-27 Caamtech, Inc. 5-methoxytryptammonium hydrophthalate
WO2025043053A1 (en) * 2023-08-23 2025-02-27 Caamtech, Inc. 4-methoxy-n,n-dicyclopropyltryptammonium chloride

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