Cooley Docket No.: STBI-081/001WO PHARMACEUTICAL COMPOSITIONS COMPRISING (R)-1-(5-METHOXY-1H- INDOL-1-YL)-N,N- DIMETHYLPROPAN-2-AMINE OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF CROSS-REFERENCE TO RELATED APPLICATIONS [0001] This application claims priority to and the benefit of U.S. Provisional Application No. 63/496,337, filed on April 14, 2023, which is incorporated by reference herein in their entirety for all purposes. BACKGROUND [0002] The present disclosure relates to pharmaceutical compositions comprising (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or pharmaceutically acceptable salts thereof. There exists a need in the art to for pharmaceutical compositions comprising (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or pharmaceutically acceptable salts thereof, and excipients, for the treatment of diseases and disorders. The present disclosure addresses the need. SUMMARY [0003] In some aspects, the present disclosure provides a pharmaceutical composition comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or a pharmaceutically acceptable salt thereof, and an excipient. [0004] In some aspects, the present disclosure relates to a pharmaceutical composition comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate salt (e.g., amorphous (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, a crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, such as (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A, (R)- 1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B, (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I, (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II, (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a, (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5, (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 6, or a mixture thereof), and an excipient.
Cooley Docket No.: STBI-081/001WO [0005] In some aspects, the present disclosure provides a pharmaceutical composition for use in treating or preventing a disease or disorder disclosed herein. [0006] In some aspects, the present disclosure provides a pharmaceutical composition for use in treating a disease or disorder disclosed herein. [0007] In some aspects, the present disclosure provides use of a pharmaceutical composition in the manufacture of a medicament for treating or preventing a disease or disorder disclosed herein. [0008] In some aspects, the present disclosure provides use of a pharmaceutical composition in the manufacture of a medicament for treating a disease or disorder disclosed herein. [0009] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. In the specification, the singular forms also include the plural unless the context clearly dictates otherwise. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present disclosure, suitable methods and materials are described below. All publications, patent applications, patents and other references mentioned herein are incorporated by reference. The references cited herein are not admitted to be prior art to the claimed invention. In the case of conflict, the present specification, including definitions, will control. In addition, the materials, methods and examples are illustrative only and are not intended to be limiting. In the case of conflict between the chemical structures and names of the compounds disclosed herein, the chemical structures will control. [0010] Other features and advantages of the disclosure will be apparent from the following detailed description and claims. BRIEF DESCRIPTION OF FIGURES [0011] FIG. 1 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A. [0012] FIG. 2 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A. [0013] FIG. 3 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form A (wet pellet). [0014] FIG. 4 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form A.
Cooley Docket No.: STBI-081/001WO [0015] FIG. 5 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form A prepared as outlined in Example 1. [0016] FIG. 6 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form A prepared as outlined in Example 1. [0017] FIG. 7 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form B (wet pellet). [0018] FIG. 8 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine monofumarate Form B. [0019] FIG. 9 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I prepared as outlined in Example 2. [0020] FIG. 10 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I (wet pellet). [0021] FIG. 11 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II prepared as outlined in Example 2. [0022] FIG. 12 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a (wet pellet). [0023] FIG. 13 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a (wet pellet). [0024] FIG. 14 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5, isolated from MIBK overlaid with a XRPD diffractogram for the amorphous fumarate salt. [0025] FIG. 15 illustrates a XRPD diffractogram of crystalline (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 6 (wet pellet). [0026] FIG. 16 illustrates a UV Spectrum of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine. [0027] FIG. 17 illustrates (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Injector Linearity. [0028] FIG. 18 illustrates a 2μL (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine Injection, Full Scale. [0029] FIG. 19 illustrates a 2μL (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine Injection, Expanded Scale. [0030] FIG. 20 illustrates an Example T30 day API Chromatogram.
Cooley Docket No.: STBI-081/001WO DETAILED DESCRIPTION [0031] The present disclosure relates to pharmaceutical compositions comprising (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine having the following chemical structure:

[0032] The present disclosure relates to a pharmaceutical composition comprising (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or a pharmaceutically acceptable salt thereof, and an excipient. [0033] In some embodiments, the pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine. [0034] In some embodiments, the pharmaceutical composition of the present disclosure comprises a pharmaceutically acceptable salt of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine. [0035] In some embodiments, the pharmaceutically acceptable salt of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine is (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate salt, also known as (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate, and having the structural formula:

. [0036] In some embodiments, the pharmaceutical composition of the present disclosure comprises a (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine racemate, or a pharmaceutically acceptable salt thereof. [0037] In some embodiments, the pharmaceutical composition of the present disclosure comprises a pharmaceutically acceptable salt of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine. [0038] In some embodiments, the pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate salt.
Cooley Docket No.: STBI-081/001WO [0039] Solid forms of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine are disclosed in PCT/US2022/079993 which is incorporated by reference herein in its entirety for all purposes. [0040] In some embodiments, the pharmaceutical composition of the present disclosure comprises amorphous (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, a crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, such as (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate hemi-Form II, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 6, or a mixture thereof. [0041] In some embodiments, the pharmaceutical composition of the present disclosure comprises a crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate, such as (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 6, or a mixture thereof. [0042] In some embodiments, the pharmaceutical composition of the present disclosure comprises pure (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A (i.e., Form A not in mixture with one or more of Form B, Form I, Form II, Pattern 3a, Pattern 5, and Pattern 6). In some embodiments, the pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A, wherein the (R)-1-(5-methoxy-1H-indol-1- yl)-N,N-dimethylpropan-2-amine fumarate monoForm A is mixed with Form B, Form I, Form II, Pattern 3a, Pattern 5, and Pattern 6. In some embodiments, the amount of one or more of Form B, Form I, Form II, Pattern 3a, Pattern 5, and Pattern 6 as present in the mixture with the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine
Cooley Docket No.: STBI-081/001WO monofumarate Form A is less than 50%, less than 40%, less than 30%, less than 20%, less than 15%, less than 10%, less than 9%, less than 8%, less than 7%, less than 6%, less than 5%, less than 4%, less than 3%, less than 2%, less than 1%, less than 0.5%, less than 0.2%, or less than 0.1%, wt/wt, individually or in aggregate. [0043] In some embodiments, the pharmaceutical composition comprises one or more excipients selected from the group consisting of a filler, a binder, a glidant, a lubricant, a disintegrant, and a plasticizer. [0044] In some embodiments, the filler is selected from the group consisting of lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, silicified microcrystalline cellulose, and maltose, and a combination thereof. [0045] In some embodiments, the binder is selected from the group consisting of povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, ethyl cellulose, and PEO 1NF, and a combination thereof. [0046] In some embodiments, the glidant is selected from the group consisting of talc and colloidal silicon dioxide, and a combination thereof. [0047] In some embodiments, the lubricant is selected from the group consisting of magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, and PEO 1NF, and a combination thereof. [0048] In some embodiments, the disintegrant is selected from the group consisting of sodium starch glycolate, croscarmellose sodium, polyplasdone, and L-HPC, and a combination thereof. [0049] In some embodiments, the plasticizer comprises polyethylene glycol. [0050] In some embodiments, the pharmaceutical composition may further comprise a film coating. [0051] In some embodiments, the film coating comprises Opadry. [0052] In some embodiments, the pharmaceutical composition may further comprise a release controlling polymer. [0053] In some embodiments, the release controlling polymer is selected from the group consisting of hypromellose, ethyl cellulose, and methacrylic acid copolymer, and a combination thereof. [0054] In some embodiments, the pharmaceutical composition may further comprise a capsule shell.
Cooley Docket No.: STBI-081/001WO [0055] In some embodiments, the capsule shell is selected from the group consisting of HPMC capsule shell and gelatin capsule shell. [0056] In some embodiments, the pharmaceutical composition of the present disclosure optionally comprises a capsule shell selected from the group consisting of HPMC capsule shell and gelatin capsule shell and one or more excipients, wherein the excipient is selected from the group consisting of lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, talc, colloidal silicon dioxide, magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, sodium starch glycolate, croscarmellose sodium, polyplasdone, L-HPC, Opadry, ethyl cellulose, silicified microcrystalline cellulose, maltose, polyethylene glycol, PEO 1NF, and methacrylic acid copolymer, and a combination thereof. [0057] In some embodiments, the excipient is not Neusilin UFL2, sodium carboxy methyl cellulose, polyplasdone, or Opadry. [0058] In some embodiments, the pharmaceutical composition of the present disclosure optionally comprises a capsule shell comprising an HPMC capsule shell and one or more excipients, wherein the excipient is selected from the group consisting of lactose monohydrate, maize starch, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, povidone, hydroxypropyl cellulose, hypromellose, dextrates, alginic acid, talc, colloidal silicon dioxide, magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, sodium starch glycolate, croscarmellose sodium, L-HPC, ethyl cellulose, silicified microcrystalline cellulose, maltose, polyethylene glycol, PEO 1NF, and methacrylic acid copolymer, and a combination thereof. [0059] In some embodiments, the one or more excipients comprise lactose monohydrate. [0060] In some embodiments, the one or more excipients comprise maize starch. [0061] In some embodiments, the one or more excipients comprise microcrystalline cellulose. [0062] In some embodiments, the one or more excipients comprise dicalcium phosphate. [0063] In some embodiments, the one or more excipients comprise mannitol. [0064] In some embodiments, the one or more excipients comprise PROSOLV® EASYtab Nutra CM. [0065] In some embodiments, the one or more excipients comprise isomalt. [0066] In some embodiments, the one or more excipients comprise povidone.
Cooley Docket No.: STBI-081/001WO [0067] In some embodiments, the one or more excipients comprise hydroxypropyl cellulose. [0068] In some embodiments, the one or more excipients comprise hypromellose. [0069] In some embodiments, the one or more excipients comprise dextrates. [0070] In some embodiments, the one or more excipients comprise alginic acid. [0071] In some embodiments, the one or more excipients comprise talc. [0072] In some embodiments, the one or more excipients comprise colloidal silicon dioxide. [0073] In some embodiments, the one or more excipients comprise magnesium stearate. [0074] In some embodiments, the one or more excipients comprise sodium stearyl fumarate. [0075] In some embodiments, the one or more excipients comprise hydrogenated vegetable oil. [0076] In some embodiments, the one or more excipients comprise stearic acid. [0077] In some embodiments, the one or more excipients comprise sodium starch glycolate. [0078] In some embodiments, the one or more excipients comprise croscarmellose sodium. [0079] In some embodiments, the one or more excipients comprise L-HPC. [0080] In some embodiments, the one or more excipients comprise ethyl cellulose. [0081] In some embodiments, the one or more excipients comprise silicified microcrystalline cellulose. [0082] The present disclosure relates to a pharmaceutical composition comprising (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or a pharmaceutically acceptable salt thereof, and a one or more excipients, wherein the one or more excipients comprise maltose. [0083] In some embodiments, the one or more excipients comprise polyethylene glycol. [0084] In some embodiments, the one or more excipients comprise PEO 1NF. [0085] In some embodiments, the one or more excipients comprise methacrylic acid copolymer. [0086] In some embodiments, the pharmaceutical composition is stable (e.g., no or little impurity from (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof) under various storage conditions (e.g., at an elevated temperature and/or elevated humidity). [0087] In some embodiments, after storing for at least 15 days at 40°C/75%RH, the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 95% pure when measured by high pressure liquid chromatography (HPLC). [0088] In some embodiments, after storing for at least 15 days at 40°C/75%RH, the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable
Cooley Docket No.: STBI-081/001WO salt thereof is at least 96% pure when measured by high pressure liquid chromatography (HPLC). [0089] In some embodiments, after storing for at least 15 days at 40°C/75%RH, the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 97% pure when measured by high pressure liquid chromatography (HPLC). [0090] In some embodiments, after storing for at least 15 days at 40°C/75%RH, the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 98% pure when measured by high pressure liquid chromatography (HPLC). [0091] In some embodiments, after storing for at least 15 days at 40°C/75%RH, the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 99% pure when measured by high pressure liquid chromatography (HPLC). [0092] In some embodiments, after storing for 30 days at 40°C/75%RH, the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 95% pure when measured by high pressure liquid chromatography (HPLC). [0093] In some embodiments, after storing for 30 days at 40°C/75%RH, the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 96% pure when measured by high pressure liquid chromatography (HPLC). [0094] In some embodiments, after storing for 30 days at 40°C/75%RH, the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 97% pure when measured by high pressure liquid chromatography (HPLC). [0095] In some embodiments, after storing for 30 days at 40°C/75%RH, the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 98% pure when measured by high pressure liquid chromatography (HPLC). [0096] In some embodiments, after storing for 30 days at 40°C/75%RH, the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine, or the pharmaceutically acceptable salt thereof is at least 99% pure when measured by high pressure liquid chromatography (HPLC).
Cooley Docket No.: STBI-081/001WO [0097] The present disclosure also relates to processes for the preparation of these pharmaceutical compositions and to their use in the treatment of disorders in a subject in need thereof. Pharmaceutical Compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A [0098] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A. [0099] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0100] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^ In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0101] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^ radiation).In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0102] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0103] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0104] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ or ±0.0 °2^^^&X^.Į^ radiation). [0105] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^^^,Q^VRPH^HPERGLPHQWV^^WKH^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^ ^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0106] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^RU^ ±0.0 °^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^DQG^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0107] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)- N,N-dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0108] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^ [0109] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-
Cooley Docket No.: STBI-081/001WO methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0110] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ and 34.0 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0111] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0112] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or
Cooley Docket No.: STBI-081/001WO more XRPD peaks selected from the grRXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X .Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0113] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 22.3 ^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU ^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0114] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^
Cooley Docket No.: STBI-081/001WO ^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^ radiation). [0115] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^.8 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 22.3 ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^Uadiation). [0116] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, or nineteen XRPD peaks selected from those set forth in Table A, as PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ. Table A: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A as shown in FIG.1, as measured ZLWK^&X^.Į^UDGLDtion. Net Gross Rel. Signal 2
-^ (°) d Intensity Intensity Intensity number Value (counts) (counts) (%) Signal 13.3 6.66 259.1 316.1 19.6 #1
Cooley Docket No.: STBI-081/001WO Signal 13.9 6.36 348.6 406.8 26.3 #2 Signal 15.5 5.71 161.2 222.6 12.2 #3 Signal
#4 15.8 5.61 451.0 514.1 34.1 Signal
#5 18.3 4.84 286.1 367.1 21.6 Signal
#6 18.8 4.71 309.7 397.7 23.4 Signal
#7 19.3 4.59 655.8 748.2 49.6 Signal
#8 20.7 4.28 448.6 549.2 33.9 Signal
#9 21.2 4.19 529.5 633.3 40.0 Signal
#10 21.4 4.14 531.4 636.2 40.2 Signal
#11 22.3 3.99 1323.1 1428.1 100.0 Signal
#12 23.0 3.86 149.6 249.9 11.3 Signal
#13 24.3 3.66 170.1 258.4 12.9 Signal
#14 24.9 3.57 236.3 318.5 17.9 Signal
#15 28.0 3.19 365.6 453.9 27.6 Signal
#16 28.9 3.09 312.5 399.2 23.6 Signal
#17 31.8 2.81 210.2 285.0 15.9
Cooley Docket No.: STBI-081/001WO Signal #
18 34.0 2.63 270.9 355.3 20.5 Signal #
19 37.2 2.42 143.4 234.5 10.8 [0117] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 1^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ. [0118] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A. [0119] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 14.0 ^^^^ 15.9 ^^^^ and 22.3 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^.In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 14.0 ^^^^ 15.9 ^^^^ and 22.3 ^^^ (±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0120] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0121] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^^,Q^ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0122] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 13.4 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0123] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting oI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0124] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks aW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0125] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)- N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0126] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^
Cooley Docket No.: STBI-081/001WO ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0127] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 22.3 ^^^^^DQG^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 21.5^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0128] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 21.5 ^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0129] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 21.5 ^^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^19.2 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0130] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the groXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 21.5 ^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0131] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 21.5 ^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X .Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure
Cooley Docket No.: STBI-081/001WO comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 21.3 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0132] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting oI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 21.3 ^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU ^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į1 radiation). [0133] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 21.3 ^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^ radiation).
Cooley Docket No.: STBI-081/001WO [0134] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, or eighteen XRPD peaks selected from those set forth in Table B, as measured ZLWK^&X^.Į^UDGLDWLRQ. Table B: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A as shown in FIG.2, as measured ZLWK^&X^.Į^UDGLDWLRQ. Signal 2-^ (°) d Value Net Gross Rel. number Intensity Intensity Intensity (counts) (counts) (%) Signal #1 10.1 8.78 554.9 650.3 12.3 Signal #2 13.4 6.62 1186.0 1292.9 26.2 Signal #3 14.0 6.32 1684.2 1793.9 37.2 Signal #4 15.6 5.68 810.5 932.6 17.9 Signal #5 15.9 5.58 2220.1 2346.2 49.1 Signal #6 18.4 4.82 766.6 921.6 17.0 Signal #7 18.9 4.69 1061.8 1230.2 23.5 Signal #8 19.2 4.62 876.7 1051.4 19.4 Signal #9 19.4 4.58 1606.4 1784.3 35.5 Signal #10 20.8 4.26 962.8 1157.4 21.3 Signal #11 21.3 4.16 1373.5 1572.2 30.4 Signal #12 21.5 4.13 1288.6 1488.0 28.5 Signal #13 22.3 3.98 4522.3 4718.8 100.0 Signal #14 23.2 3.84 596.9 781.2 13.2 Signal #15 24.4 3.64 515.6 688.9 11.4 Signal #16 25.0 3.56 740.1 905.6 16.4 Signal #17 28.1 3.17 804.6 970.8 17.8 Signal #18 29.1 3.07 720.0 878.9 15.9
Cooley Docket No.: STBI-081/001WO [0135] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 2^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ. [0136] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A. [0137] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 19.3 ^^^^ 19.6 ^^^^ and 22.6 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^.In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 19.3 ^^^^ 19.6 ^^^^ and 22.6 ^^^ (±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0138] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^radiation). [0139] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 18.5 ^^^^ 19.3 ^^^^ 19.6 ^^^^ 21.6 ^^^^ and 22.6 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 18.5 ^^^^ 19.3 ^^^^ 19.6 ^^^^ 21.6 ^^^^ and 22.6 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0140] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0141] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 18.5 ^^^^ 19.3 ^^^^ 19.6 ^^^^ 21.6 ^^^^ 21.7 ^^^^ 22.6 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 18.5 ^^^^ 19.3 ^^^^ 19.6 ^^^^ 21.6 ^^^^ 21.7 ^^^^ 22.6 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0142] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 18.5 ^^^^ 19.3 ^^^^ 19.6 ^^^^ 21.6 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.6 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 18.5 ^^^^ 19.3 ^^^^ 19.6 ^^^^ 21.6 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.6 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0143] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 18.5 ^^^^ 19.3 ^^^^ 19.6 ^^^^ 21.6 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.6 ^^^^ 23.9 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^.0 ^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^SUHVHQW^ disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 18.5 ^^^^ 19.3 ^^^^ 19.6 ^^^^ 21.6 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.6 ^^^^ 23.9 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0144] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^ the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)- N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
Cooley Docket No.: STBI-081/001WO ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0145] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ (±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0146] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^ ^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0147] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
Cooley Docket No.: STBI-081/001WO DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^(±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0148] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0149] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0150] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^ 16.1 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0151] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0152] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consistLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
Cooley Docket No.: STBI-081/001WO ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0153] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^ present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0154] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^ of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)- N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
Cooley Docket No.: STBI-081/001WO ^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0155] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG ^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^ of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)- N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0156] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the grouS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0157] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, or twenty-three XRPD peaks selected from those set forth in Table C^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Table C: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A as shown in FIG.3, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ Signal 2-^ (°) d Value Net Gross Rel. number Intensity Intensity Intensity (counts) (counts) (%) Signal 10.3 8.58 169.1 350.6 18.1 #1 Signal 13.6 6.50 286.0 545.7 30.6 #2 Signal 14.2 6.24 339.2 620.7 36.3 #3 Signal 16.1 5.51 328.6 691.8 35.2 #5 Signal 16.2 5.47 310.8 677.7 33.3 #4 Signal 16.9 5.24 158.5 551.1 17.0 #6 Signal 17.8 4.98 351.8 771.4 37.7 #7 Signal 18.5 4.79 464.5 900.4 49.7 #8 Signal 19.3 4.60 542.6 991.7 58.1 #9 Signal 19.6 4.52 716.5 1170.2 76.7 #10
Cooley Docket No.: STBI-081/001WO Signal #
11 21.1 4.21 325.1 788.7 34.8 Signal #
12 21.6 4.11 533.8 996.9 57.2 Signal #
13 21.7 4.10 420.6 883.5 45.0 Signal #
14 22.6 3.94 933.9 1390.6 100.0 Signal #
16 23.6 3.77 398.5 840.6 42.7 Signal #
17 23.6 3.76 412.2 853.5 44.1 Signal #
15 23.9 3.72 377.4 813.5 40.4 Signal #
18 25.2 3.53 403.3 806.0 43.2 Signal #
19 28.3 3.15 286.5 627.2 30.7 Signal #
20 29.3 3.04 150.8 473.9 16.1 Signal #
22 29.8 2.99 156.9 467.8 16.8 Signal #
21 29.9 2.99 163.3 473.4 17.5 Signal #
23 36.7 2.45 95.9 313.9 10.3 [0158] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 3^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^
Cooley Docket No.: STBI-081/001WO [0159] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A. [0160] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ (^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^.In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0161] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks aW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0162] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^9.2 ^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0163] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^^^,Q^ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0164] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU ^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0165] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLon). [0166] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^or ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^^,Q^VRPH^HPERGLPHQWV^^WKH^FRPSRXQG^PRQRIXPDUDWH^VDOW^LV^ crystalline polymorphic Form A is crystalline and is characterized by XRPD peaks at 15.9 ^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0167] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^ ^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)- N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0168] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical
Cooley Docket No.: STBI-081/001WO composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0169] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 28.3 ^^^^^DQG^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^ 25.2 ^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0170] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^.1 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^ [0171] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0172] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 22.6 ^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0173] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 21.6 ^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X .Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0174] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU ^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0175] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^ radiation). [0176] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, or eighteen XRPD peaks selected from those set forth in Table D, as measured ZLWK^&X^.Į^UDGLDWLRQ^ Table D: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A as shown in FIG.4, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ Net Gross Rel. Signal number
2-^^(°) d V
alue Intensity Intensity Intensity (counts) (counts) (%) Signal #1 10.3 8.59 447.0 567.1 10.7 Signal #2 13.6 6.50 472.0 623.8 11.3 Signal #3 14.2 6.24 712.7 870.2 17.1 Signal #4 15.9 5.58 1094.4 1286.5 26.3 Signal #5 16.1 5.51 1803.9 2000.9 43.3 Signal #6 17.0 5.21 524.9 738.8 12.6 Signal #7 18.7 4.75 498.7 763.4 12.0 Signal #8 19.2 4.61 1141.3 1424.3 27.4 Signal #9 19.5 4.55 1054.1 1343.4 25.3 Signal #10 21.2 4.18 635.5 947.9 15.3 Signal #12 21.3 4.17 715.0 1027.4 17.2 Signal #11 21.6 4.12 1330.4 1642.4 31.9 Signal #13 22.6 3.94 4165.8 4467.5 100.0 Signal #14 25.2 3.53 609.3 857.8 14.6 Signal #15 25.5 3.49 499.2 742.4 12.0 Signal #16 28.3 3.15 800.0 1030.3 19.2 Signal #17 29.2 3.06 972.6 1197.2 23.3 Signal #18 34.3 2.61 431.9 624.2 10.4 [0177] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 4^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^
Cooley Docket No.: STBI-081/001WO [0178] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A. [0179] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^DQG^14.1 ^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^.In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^DQG^14.1 ^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0180] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^DQG^ 14.1 ^^^, and 13.5 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^ 14.1 ^^^, and 13.5 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGiation). [0181] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, and 19.5 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^Vome embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^ 14.1 ^^^, 13.5 ^^^, and 19.5 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0182] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, and 21.7 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^ 14.1 ^^^, 13.5 ^^^, 19.5 ^^^, and 21.7 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0183] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, and 21.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, and 21.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0184] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 °2^, 21.7 ^^^, 21.4 ^^^, and 21.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^SUHVHQW^GLVFORVXUH^ comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, and 21.0 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0185] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, and 19.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^ present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, and 19.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0186] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, and 15.7 ^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^ the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)- N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, and 15.7 ^^^ (±0.^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0187] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1
Cooley Docket No.: STBI-081/001WO ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, and 18.5 ^^^ (±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, and 18.5 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0188] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, and 10.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, and 10.2 ^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0189] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, and 28.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, and 28.2 ^^^ (±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0190] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, 28.2 ^^^, and 29.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^ 14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, 28.2 ^^^, and 29.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0191] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, 28.2 ^^^, 29.2 ^^^, and 23.3 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^ 14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, 28.2 ^^^, 29.2 ^^^, and 23.3 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0192] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, 28.2 ^^^, 29.2 ^^^, 23.3 ^^^, and 25.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure
Cooley Docket No.: STBI-081/001WO comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, 28.2 ^^^, 29.2 ^^^, 23.3 ^^^, and 25.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0193] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, 28.2 ^^^, 29.2 ^^^, 23.3 ^^^, 25.2 ^^^, and 24.5 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by XRPD peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, 19.5 ^^^, 21.7 ^^^, 21.4 ^^^, 21.0 ^^^, 19.1 ^^^, 15.7 ^^^, 18.5 ^^^, 10.2 ^^^, 28.2 ^^^, 29.2 ^^^, 23.3 ^^^, 25.2 ^^^, and 24.5 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0194] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form A is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeen XRPD peaks selected from those set forth in Table E or Table F, as measured ZLWK^&X^.Į^UDGLDWLRQ^ Table E. A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A as shown in FIG.5, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ Signal Position. d- Relative No.
>^^^@ spacing >c@ Intensity >^@ 1 10.2118 8.65535 18.19 2 13.4987 6.55428 43.98
Cooley Docket No.: STBI-081/001WO 3 14.1419 6.25761 55.37 4 15.6865 5.64474 21.11 5 16.0097 5.5315 67.09 6 18.5332 4.78363 19.71 7 19.0629 4.65188 21.73 8 19.526 4.54259 41.34 9 20.9831 4.2303 27.12 10 21.3971 4.14939 29.15 11 21.6587 4.09986 36.3 12 22.4904 3.95009 100 13 23.2901 3.81622 12.15 14 24.5427 3.62422 10.23 15 25.1714 3.53511 10.3 16 28.2412 3.15743 15.82 17 29.1829 3.05765 13.51 Table F. A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form A as shown in FIG. 6, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ Signal Position d-spacing >c@ Relative No. >^^^@ Intensity >^@ 1 10.2121 8.65507 17.73 2 13.5021 6.55265 41.1 3 14.1435 6.25689 50.24 4 15.7017 5.63931 20.51 5 16.0141 5.52998 64.28 6 18.5312 4.78413 19.76 7 19.0784 4.64812 22.95 8 19.5294 4.54179 35.8 9 20.9861 4.22971 27.92 10 21.4019 4.14847 29.07 11 21.6681 4.09811 33.8 12 22.4888 3.95036 100 13 23.2878 3.81661 13.57 14 24.5339 3.6255 10.59 15 25.1566 3.53715 13.37 16 28.2376 3.15782 16.44 17 29.1788 3.05808 14.71 [0195] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form A, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine monofumarate polymorph Form A is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 5 or FIG. 6^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. [0196] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and is non-hygroscopic. [0197] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and is solvated. [0198] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and is unsolvated. [0199] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and is anhydrous. [0200] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form A and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate. Pharmaceutical Compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form B [0201] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B. [0202] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 17.8 ^^^^ 19.5 ^^^^ and 20.3 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at 17.8 ^^^^ 19.5 ^^^^ and 20.3 ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0203] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ and 23.6 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ and 23.6 ^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0204] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 16.8 ^^^^ 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ and 23.6 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at 16.8 ^^^^ 17.8 ^^^^ 19.5 ^^^^ 20.3 °2^^ and 23.6 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0205] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.1 ^^^^^^^^^ ^^^^ 17.8 ^^^^ ^^^^^^^^^ 20.3 ^^^^^DQG 23.6 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at 15.1 ^^^^^^^^^ ^^^^ 17.8 ^^^^ ^^^^^^^^^ 20.3 ^^^^^DQG 23.6 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0206] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 9.5 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ and 23.6 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at 9.5 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ and 23.6 ^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^ [0207] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 9.5 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ 23.6 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at 9.5 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ 23.6 ^^^^ and 29.8 ^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0208] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 5.9 ^^^^ 9.5 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ 23.6 ^^^^ and 29.8 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at 5.9 ^^^^ 9.5 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ 23.6 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0209] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by one, two, three, four, five, six, seven, eight, or nine XRPD peaks selected from those set forth in Table E^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Table E: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form B as shown in FIG. 7, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ Signal number 2-^ (°) d Value Net Intensity Gross Rel. Intensity Intensity (counts) (counts) (%) Signal 5.9 15.08 55.5 278.2 11.9 #1 Signal 9.5 9.34 75.3 242.5 16.2 #2 Signal 15.1 5.87 107.8 393.0 23.2 #3 Signal 16.8 5.26 218.1 551.5 47.0 #4 Signal 17.8 4.98 414.7 769.8 89.3 #5 Signal 19.5 4.54 464.1 843.6 100.0 #6 Signal 20.3 4.36 345.3 730.3 74.4 #7 Signal 23.6 3.77 340.2 708.2 73.3 #8 Signal 29.8 3.00 74.1 318.7 16.0 #9 [0210] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 7^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ [0211] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B.
Cooley Docket No.: STBI-081/001WO [0212] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^DQG^^^^^ ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^ ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0213] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWion). [0214] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0215] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^^,Q^ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0216] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU ^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 23.5 ^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0217] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting RI^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks
Cooley Docket No.: STBI-081/001WO DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^ radiation). [0218] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0219] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^ ^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)- N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0220] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 28.3 ^^^^^DQG^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^
Cooley Docket No.: STBI-081/001WO pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0221] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 23.5 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^ radiation). [0222] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more, or three or more XRPD peaks VHOHFWHG^IURP^WKH^JURXS^FRQVLVWLQJ^RI^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B is crystalline and is characterized by XRPD peaks DW^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0223] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, or fourteen XRPD peaks selected from those set forth in Table F^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Table F: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate polymorph Form B as shown in FIG. 8, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ Signal number 2-^ (°) d Value Net Gross Rel. Intensity Intensity Intensity (counts) (counts) (%) Signal #1 9.4 9.42 98.8 209.9 22.9 Signal #2 11.8 7.51 43.5 177.3 10.1 Signal #3 13.6 6.53 72.9 241.4 16.9 Signal #4 13.7 6.44 109.5 283.5 25.4 Signal #5 14.9 5.93 96.6 302.1 22.4 Signal #6 15.0 5.91 67.0 273.7 15.5 Signal #7 16.7 5.30 264.5 515.9 61.3 Signal #8 17.6 5.02 431.5 705.7 100.0 Signal #9 19.4 4.56 420.1 725.7 97.4 Signal #10 23.5 3.79 375.0 685.9 86.9 Signal #11 24.7 3.60 282.0 576.6 65.3 Signal #12 24.9 3.58 248.8 540.7 57.7 Signal #13 28.3 3.15 71.0 308.9 16.5 Signal #14 29.5 3.03 111.1 329.4 25.8 [0224] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate polymorph Form B, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate polymorph Form B is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 8^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ [0225] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and is non-hygroscopic.
Cooley Docket No.: STBI-081/001WO [0226] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and is solvated. [0227] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and is unsolvated. [0228] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and is anhydrous. [0229] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine monofumarate is crystalline Form B and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate. Pharmaceutical Compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine Hemi-fumarate Form I [0230] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I. [0231] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 15.9 ^^^^ 19.4 ^^^^ and 21.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.9 ^^^^ 19.4 ^^^^ and 21.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0232] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-
Cooley Docket No.: STBI-081/001WO methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0233] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.2 ^^^^^^^^^ ^^^^ 19.4 ^^^^ ^^^^^^^^^ 22.5 ^^^^^DQG 27.1 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.2 ^^^^^^^^^ ^^^^ 19.4 ^^^^ ^^^^^^^^^ 22.5 ^^^^^DQG 27.1 ^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0234] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0235] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.4 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure
Cooley Docket No.: STBI-081/001WO comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 13.4 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDtion). [0236] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.4 ^^^^ 13.7 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^, 19.4 ^^^^ 21.0 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^SUHVHQW^ disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi- fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 13.4 ^^^^ 13.7 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0237] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 11.7 ^^^^ 13.4 ^^^^ 13.7 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^ present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 11.7 ^^^^ 13.4 ^^^^ 13.7 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0238] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 11.7 ^^^^ 13.4 ^^^^ 13.7 ^^^^
Cooley Docket No.: STBI-081/001WO 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 21.6 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^ of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 11.7 ^^^^ 13.4 ^^^^ 13.7 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 21.6 ^^^^ 22.5 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0239] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 11.7 ^^^^ 13.4 ^^^^ 13.7 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 21.6 ^^^^ 22.5 ^^^^ 23.2 ^^^^ and 27.1 ^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 11.7 ^^^^ 13.4 ^^^^ 13.7 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 21.6 ^^^^ 22.5 ^^^^ 23.2 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^ [0240] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, or twelve XRPD peaks selected from those set forth in Table G^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Table G: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I as shown in FIG. 9, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ Gross Rel. Signal Net Intensity 2
-^ (°) d Intensity Intensity number Value (counts) (counts) (%) Signal #1 11.7 7.58 396.3 550.9 11.2
Cooley Docket No.: STBI-081/001WO Signal #2 13.4 6.59 537.7 711.0 15.2 Signal #3 13.7 6.47 523.8 702.8 14.8 Signal #4 15.2 5.82 1058.1 1311.0 29.9 Signal #5 15.9 5.57 3537.4 3823.3 100.0 Signal #6 18.9 4.69 600.6 984.8 17.0 Signal #7 19.4 4.58 1172.9 1566.2 33.2 Signal #8 21.0 4.22 1658.6 2060.6 46.9 Signal #9 21.6 4.12 380.3 778.0 10.7 Signal 22.5 3.95 613.9 995.6 17.4 #10 Signal 23.2 3.83 359.4 725.5 10.2 #11 Signal 27.1 3.29 1088.3 1356.6 30.8 #12 [0241] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 9^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ [0242] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I. [0243] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^.
Cooley Docket No.: STBI-081/001WO [0244] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0245] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.4 ^^^^ 16.0 ^^^^ 19.5 ^^^^ 21.2 ^^^^ and 27.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.4 ^^^^ 16.0 ^^^^ 19.5 ^^^^ 21.2 ^^^^ and 27.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0246] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.4 ^^^^^^^^^ ^^^^ 19.5 ^^^^ ^^^^^^^^^ 22.6 ^^^^^DQG 27.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.4 ^^^^^^^^^ ^^^^ 19.5 ^^^^ ^^^^^^^^^ 22.6 ^^^^^DQG 27.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation).
Cooley Docket No.: STBI-081/001WO [0247] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ and 27.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ and 27.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0248] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ and 27.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ and 27.2 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0249] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ 27.2 ^^^^ and 30.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^ &X^.Į^^UDGLation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi- fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized
Cooley Docket No.: STBI-081/001WO by XRPD peaks at 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ 27.2 ^^^^ and 30.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 27.2 ^^^^ and 30.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^ present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 27.2 ^^^^ and 30.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^Uadiation). [0251] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 25.0 ^^^^ 27.2 ^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^ of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 25.0 ^^^^ 27.2 ^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0252] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 25.0 ^^^^ 27.2 ^^^^ and 30.4 ^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-
Cooley Docket No.: STBI-081/001WO dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 25.0 ^^^^ 27.2 ^^^^ and 30.4 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^ [0253] In some embodiments, pharmaceutical composition of the present disclosure -1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 24.3 ^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 24.3 ^^^^ ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0254] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.7 ^^^^ 15.4 ^^^, 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 24.3 ^^^^^25.0 ^^^^ 27.2 ^^^^ 28.5 ^^^^ and 30.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.4 ^^^^ 24.3 ^^^^^25.0 ^^^^ 27.2 ^^^^ 28.5 ^^^^ and 30.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0255] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 11.8 ^^^^ 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.4 ^^^^^24.3 ^^^^ 25.0 ^^^^ 27.2 ^^^^ 28.5 ^^^^ and 30.4 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I is crystalline and is characterized by XRPD peaks at 11.8 ^^^^ 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.4 ^^^^^24.3 ^^^^ 25.0 ^^^^ 27.2 ^^^^ 28.5 ^^^^ and 30.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0256] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, or sixteen XRPD peaks selected from those set forth in Table H^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Table H: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form I as shown in FIG. 10, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ 2-^ (°) Net Gross Rel. Signal d Intensity Intensity number Value Intensity (counts) (%) (counts) Signal 11.8 7.47 362.2 495.0 11.6 #1 Signal 13.7 6.48 633.6 792.3 20.4 #2 Signal 13.7 6.47 642.5 801.5 20.6 #3 Signal 15.4 5.76 950.4 1142.3 30.5 #4 Signal 16.0 5.53 3112.9 3322.2 100.0 #5 Signal 19.2 4.62 765.7 1033.7 24.6 #6 Signal 19.5 4.54 1450.4 1723.7 46.6 #7 Signal 21.2 4.19 1975.0 2267.5 63.4 #8
Cooley Docket No.: STBI-081/001WO Signal 21.7 4.10 423.5 719.8 13.6 #9 Signal 22.6 3.93 770.3 1066.4 24.7 #10 Signal 23.4 3.79 481.9 769.3 15.5 #11 Signal 24.3 3.66 413.8 684.4 13.3 #12 Signal 25.0 3.56 440.0 690.2 14.1 #13 Signal 27.2 3.27 1495.2 1749.4 48.0 #14 Signal 28.5 3.13 376.5 627.2 12.1 #15 Signal 30.4 2.94 497.6 707.9 16.0 #16 [0257] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form I, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form I is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 10^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. [0258] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and is non-hygroscopic. [0259] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and is solvated. [0260] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and is unsolvated. [0261] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and is anhydrous. [0262] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form I and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate. Pharmaceutical Compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate Form II [0263] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II.
Cooley Docket No.: STBI-081/001WO [0264] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0265] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ and 26.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 15.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ and 26.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0266] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.1 ^^^^ 15.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ and 26.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 15.1 ^^^, 15.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ and 26.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0267] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.1 ^^^^^15.8 ^^^^ 19.2 ^^^^ ^^^^^^^^^ 22.4 ^^^^^DQG 26.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 15.1 ^^^^^^^^^ ^^^^ 19.2 ^^^^ ^^^^^^^^^ 22.4 ^^^^^DQG 26.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0268] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 22.4 ^^^^ and 26.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 22.4 ^^^^ and 26.9 ^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ). [0269] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 °2^^ 22.4 ^^^^ 26.9 ^^^^ and 30.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^SUHVHQW^ disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi- fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized
Cooley Docket No.: STBI-081/001WO by XRPD peaks at 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 22.4 ^^^^ 26.9 ^^^^ and 30.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0270] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.3 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 22.4 ^^^^ 26.9 ^^^^ and 30.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^SUHVHQW^ disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi- fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 13.3 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 22.4 ^^^^ 26.9 ^^^^ and 30.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0271] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.3 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 22.4 ^^^^ 24.7 ^^^^ 26.9 ^^^^ and 30.2 ^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^ the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)- N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 13.3 ^^^, 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 22.4 ^^^^ 24.7 ^^^^ 26.9 ^^^^ and 30.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0272] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.3 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^ 24.7 ^^^^ 26.9 ^^^^ and 30.2 ^^^ (±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-
Cooley Docket No.: STBI-081/001WO dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 13.3 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^ 24.7 ^^^^ 26.9 ^^^^ and 30.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^ [0273] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.3 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^ 24.7 ^^^^ 26.9 ^^^^^28.2 ^^^^ and 30.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 13.3 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^ 24.7 ^^^^ 26.9 ^^^^^28.2 ^^^^ and 30.2 ^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0274] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.3 ^^^^ 13.5 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 °^^^ 24.7 ^^^^^26.9 ^^^^^28.2 ^^^^ and 30.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 13.3 ^^^, 13.5 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^ 24.7 ^^^^^26.9 ^^^^^28.2 ^^^^ and 30.2 ^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0275] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.3 ^^^^ 13.5 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^ 23.1 ^^^^ 24.7 ^^^^ 26.9 ^^^^ 28.2 ^^^^ and 30.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 13.3 ^^^^ 13.5 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^ 23.1 ^^^^ 24.7 ^^^^ 26.9 ^^^^ 28.2 ^^^^ and 30.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0276] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 11.5 ^^^^ 13.3 ^^^^ 13.5 ^^^^ 15.1 ^^^^ 15.8 °2^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^^23.1 ^^^^ 24.7 ^^^^ 26.9 ^^^^ 28.2 ^^^^ and 30.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks at 11.5 ^^^, 13.3 ^^^^ 13.5 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^^23.1 ^^^^ 24.7 ^^^^ 26.9 ^^^^ 28.2 ^^^^ and 30.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0277] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 11.5 ^^^^ 13.3 ^^^^ 13.5 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^^23.1 ^^^^ 24.0 ^^^^ 24.7 ^^^^ 26.9 ^^^^ 28.2 ^^^^ and 30.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by XRPD peaks
Cooley Docket No.: STBI-081/001WO at 11.5 ^^^^ 13.3 ^^^^ 13.5 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^^23.1 ^^^^ 24.0 ^^^^ 24.7 ^^^^ 26.9 ^^^^ 28.2 ^^^^ and 30.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0278] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, or sixteen XRPD peaks selected from those set forth in Table I^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. Table I: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate polymorph Form II as shown in FIG. 11, as PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^^ Gross Rel. Signal
d Net Intensity 2
-^ (°) Intensity Intensity number Value (counts) (counts) (%) Signal 11.5 7.66 194.5 253.7 11.8 #1 Signal 13.3 6.66 224.6 283.6 13.6 #2 Signal 13.5 6.54 208.8 268.5 12.6 #3 Signal 15.1 5.87 501.5 579.0 30.3 #4 Signal 15.8 5.62 1653.8 1737.1 100.0 #5 Signal 18.8 4.72 318.4 414.1 19.3 #6 Signal 19.2 4.61 717.1 814.7 43.4 #7 Signal 20.9 4.25 1133.9 1234.5 68.6 #8 Signal 21.4 4.14 215.3 317.8 13.0 #9 Signal 22.4 3.97 458.2 563.5 27.7 #10 Signal 23.1 3.85 208.3 312.7 12.6 #11 Signal 24.0 3.71 176.4 273.7 10.7 #12 Signal 24.7 3.60 219.7 305.7 13.3
Cooley Docket No.: STBI-081/001WO #13 Signal 26.9 3.31 726.9 822.0 44.0 #14 Signal 28.2 3.16 215.2 312.5 13.0 #15 Signal 30.2 2.96 249.3 330.5 15.1 #16 [0279] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate polymorph Form II, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate polymorph Form II is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 11^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. [0280] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and is non-hygroscopic. [0281] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and is solvated. [0282] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and is unsolvated. [0283] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and is anhydrous. [0284] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine hemi-fumarate is crystalline Form II and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate. Pharmaceutical Compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a [0285] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a. [0286] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^. [0287] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17.9 ^^^^^^^^^ ^^^^^^^^^ ^^^^ and 23.9 ^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 17.9 ^^^^^^^^^ ^^^^^^^^^ ^^^^ and 23.9 ^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0288] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ and 24.9 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ and 24.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0289] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or
Cooley Docket No.: STBI-081/001WO three or more XRPD peaks selected from the group consisting of 17.9 ^^^^^^^^^ ^^^^ 20.5 ^^^^ ^^^^^^^^^ 24.9 ^^^^^DQG 25.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 17.9 ^^^^^^^^^ ^^^^ 20.5 ^^^^ ^^^^^^^^^ 24.9 ^^^^^DQG 25.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0290] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 16.9 °2^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0291] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.9 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X .Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 13.9 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ and 25.2 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0292] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate
Cooley Docket No.: STBI-081/001WO polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.9 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ 25.2 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^ present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 13.9 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ 25.2 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0293] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.9 ^^^^ 15.2 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ 25.2 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^ present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 13.9 ^^^^ 15.2 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ 25.2 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0294] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 13.9 ^^^^ 15.2 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ 25.2 ^^^^ 28.5 ^^^^^and 29.8 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^ of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 13.9 ^^^^ 15.2 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ 25.2 ^^^^ 28.5 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0295] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 9.6 ^^^^ 13.9 ^^^^ 15.2 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ 25.2 ^^^^^28.5 ^^^^^and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 9.6 ^^^^ 13.9 ^^^^ 15.2 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ 25.2 ^^^^ 28.5 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^ [0296] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, or twelve XRPD peaks selected from those set forth in Table J^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Table J: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a as shown in FIG. 12, as measured with &X^.Į^UDGLDWLRQ^^ Gross Rel. Signal Net Intensity 2
-^ (°) d Intensity Intensity number Value (counts) (counts) (%) Signal 9.6 9.22 120.7 278.0 13.3 #1 Signal 13.9 6.35 281.2 532.2 31.1 #2 Signal 15.2 5.83 179.0 451.4 19.8 #3 Signal 16.9 5.24 302.2 623.0 33.4 #4 Signal 17.9 4.95 836.9 1191.4 92.4 #5 Signal 19.7 4.51 689.3 1085.0 76.1 #6
Cooley Docket No.: STBI-081/001WO Signal 20.5 4.33 531.8 939.2 58.7 #7 Signal 23.9 3.73 905.6 1309.3 100.0 #8 Signal 24.9 3.57 452.6 838.1 50.0 #9 Signal 25.2 3.53 400.2 778.8 44.2 #10 Signal 28.5 3.13 130.4 469.6 14.4 #11 Signal 29.8 2.99 272.1 594.7 30.0 #12 [0297] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 12^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. [0298] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a. [0299] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 18.1 ^^^^ 19.8 ^^^^ and 19.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 18.1 ^^^^ 19.8 ^^^^ and 19.9 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^. [0300] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0301] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 18.1 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 18.1 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0302] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17.6 ^^^^^^^^^ ^^^^ 19.8 ^^^^ ^^^^^^^^^ 23.6 ^^^^^DQG 24.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 17.6 ^^^^^^^^^ ^^^^ 19.8 ^^^^ ^^^^^^^^^ 23.6 ^^^^^DQG 24.0 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0303] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0304] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLon). [0305] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 14.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^SUHVHQW^ disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 14.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0306] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^ present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ and 24.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0307] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ 24.0 ^^^^ and 28.3 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^ of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ 24.0 ^^^^ and 28.3 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0308] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ 24.0 ^^^^^^^^^^^^^^ and 30.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is
Cooley Docket No.: STBI-081/001WO characterized by XRPD peaks at 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ 24.0 ^^^^^^^^^^^^^^ and 30.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^ [0309] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ 24.0 ^^^^^25.7 ^^^^ 28.3 ^^^^ and 30.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^ 24.0 ^^^^^25.7 ^^^^ 28.3 ^^^^ and 30.0 ^^^ (±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0310] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 9.5 ^^^^ 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^^24.0 ^^^^^25.7 ^^^^ 28.3 ^^^^ and 30.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 9.5 ^^^^ 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^ 23.6 ^^^^^24.0 ^^^^^25.7 ^^^^ 28.3 ^^^^ and 30.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0311] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 9.5 ^^^^ 11.9 ^^^^ 14.1 ^^^^
Cooley Docket No.: STBI-081/001WO 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^^23.6 ^^^^^24.0 ^^^^^25.7 ^^^^ 28.3 ^^^^ and 30.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 9.5 ^^^^ 11.9 ^^^^ 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^^23.6 ^^^^^24.0 ^^^^^25.7 ^^^^ 28.3 ^^^^ and 30.0 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0312] n some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 9.5 ^^^^ 11.9 ^^^^ 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^^23.6 ^^^^^24.0 ^^^^^25.7 ^^^^ 28.3 ^^^^ 30.0 ^^^^ and 31.7 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a is crystalline and is characterized by XRPD peaks at 9.5 ^^^^ 11.9 ^^^^ 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^^23.6 ^^^^^24.0 ^^^^^25.7 ^^^^ 28.3 ^^^^ 30.0 ^^^^ and 31.7 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0313] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeen XRPD peaks selected from those set forth in Table K^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. Table K: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 3a as shown in FIG. 13, as measured ZLWK^&X^.Į^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO Gross Rel. Signal
d Net Intensity 2
-^ (°) Intensity Intensity number Value (counts) (counts) (%) Signal #1 9.5 9.32 103.8 675.8 13.9 Signal #2 11.9 7.42 100.1 711.3 13.4 Signal #3 14.1 6.28 164.5 845.0 22.0 Signal #4 15.1 5.85 164.5 874.9 22.0 Signal #5 16.8 5.26 246.2 1007.3 32.9 Signal #6 17.6 5.02 378.0 1158.8 50.5 Signal #7 18.1 4.89 717.6 1508.4 95.8 Signal #8 19.0 4.66 342.8 1147.4 45.8 Signal #9 19.8 4.47 749.1 1561.2 100.0 Signal #10 19.9 4.45 676.1 1488.8 90.2 Signal #11 23.6 3.76 482.6 1276.6 64.4 Signal #12 24.0 3.71 606.7 1395.2 81.0 Signal #13 25.7 3.46 139.3 888.4 18.6 Signal #14 28.3 3.16 158.3 868.8 21.1 Signal #15 30.0 2.98 141.5 826.4 18.9 Signal #16 31.7 2.82 102.1 747.4 13.6 Signal #17 31.7 2.82 98.6 741.8 13.2 [0314] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 3a, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 3a is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 13^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. [0315] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and is non-hygroscopic. [0316] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and is solvated.
Cooley Docket No.: STBI-081/001WO [0317] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and is unsolvated. [0318] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and is anhydrous. [0319] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 3a and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate. Pharmaceutical Compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 5 [0320] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5. [0321] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 5 is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting of 7.9 ^^^^ 20.2 ^^^^ and 21.6 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5 is crystalline and is characterized by XRPD peaks at 7.9 ^^^^ 20.2 ^^^^ and 21.6 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. [0322] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 5 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5 is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0323] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 5 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 7.9 ^^^^ 15.7 ^^^^ 20.2 ^^^^ 21.6 ^^^^ and 23.7 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5 is crystalline and is characterized by XRPD peaks at 7.9 ^^^^ 15.7 ^^^^ 20.2 ^^^^ 21.6 ^^^^ and 23.7 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0324] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 5 is crystalline and is characterized by one, two, three, four, or five XRPD peaks selected from those set forth in Table L^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. Table L: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 5 as shown in FIG. 14, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ Gross Rel. Signal
d Net Intensity 2
-^ (°) Intensity Intensity number Value (counts) (counts) (%) Signal 7.9 11.25 36879.1 37068.4 100.0 #1 Signal 15.7 5.63 4937.8 5117.8 13.4 #2 Signal 20.2 4.39 8240.2 8524.7 22.3 #3 Signal 21.6 4.11 8758.6 9090.9 23.7 #4 Signal 23.7 3.76 6271.1 6582.0 17.0 #5 [0325] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 5, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-
Cooley Docket No.: STBI-081/001WO amine fumarate polymorph Pattern 5 is crystalline and is characterized by two or more or three or more XRPD peaks selected from those of FIG. 14^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. [0326] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and is non-hygroscopic. [0327] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and is solvated. [0328] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and is unsolvated. [0329] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and is anhydrous. [0330] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 5 and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate. Pharmaceutical Compositions Comprising (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6 [0331] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6. [0332] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three XRPD peaks selected from the group consisting ^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^(±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^. [0333] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate
Cooley Docket No.: STBI-081/001WO polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of ^^^^^^^^^^^^^^^^^^^^^^^^^^^, and ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0334] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 21.7 °2^^ and 23.2 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 21.7 ^^^^ and 23.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0335] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 21.7 ^^^^ 23.2 ^^^^ and 23.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 21.7 ^^^^ 23.2 ^^^^ and 23.8 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0336] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate
Cooley Docket No.: STBI-081/001WO polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 21.7 ^^^^ 23.2 ^^^^ and 23.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 21.7 ^^^^ 23.2 ^^^^ and 23.8 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^ [0337] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 21.7 ^^^^ 23.2 ^^^^ and 23.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 18.4 ^^^^ 19.3 ^^^, 20.2 ^^^^ 21.7 ^^^^ 23.2 ^^^^ and 23.8 ^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0338] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^, 14.9 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 21.7 ^^^^ 23.2 ^^^^ and 23.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^ ^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^SUHVHQW^ disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 14.9 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 21.7 ^^^^ 23.2 ^^^^ and 23.8 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO [0339] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ ^^^^^^^^^ 18.4 ^^^^^^^^^ ^^^^ 20.2 ^^^^ 20.9 ^^^^^^^^^ ^^^^ 23.2 ^^^^ and 23.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^ present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ ^^^^^^^^^ 18.4 ^^^^^^^^^ ^^^^ 20.2 ^^^^ 20.9 ^^^^^^^^^ ^^^^ 23.2 ^^^^ and 23.8 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0340] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 14.9 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 23.2 ^^^^ 23.8 ^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^ of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 14.9 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 23.2 ^^^^ 23.8 ^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0341] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 14.9 ^^^^ 18.4 °2^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^^^^^^^^^^^^and 26.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is
Cooley Docket No.: STBI-081/001WO characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 14.9 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^^^^^^^^^^^^and 26.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^ [0342] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 14.9 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^^^^^^^^^^, 23.8 ^^^^^and 26.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 14.9 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^^^^^^^^^^, 23.8 ^^^^^and 26.1 ^^^ (±0.2 ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0343] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 14.9 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^^^^^^^^^^, 23.8 ^^^^^26.1 ^^^^^DQG 29.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^ pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol- 1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 14.9 ^^^^ 18.4 ^^^^ 19.3 °^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^^^^^^^^^^, 23.8 ^^^^^26.1 ^^^^^DQG 29.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0344] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^
Cooley Docket No.: STBI-081/001WO 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^, 22.4 ^^^^^^^^^ ^^^^ 23.8 ^^^^ 26.1 ^^^^ and 29.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^ embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^, 22.4 ^^^^^^^^^ ^^^^ 23.8 ^^^^ 26.1 ^^^^ and 29.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0345] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 26.1 ^^^^ and 29.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^ some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 26.1 ^^^^ and 29.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0346] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^^21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 26.1 ^^^^ and 29.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^^
Cooley Docket No.: STBI-081/001WO 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 26.1 ^^^^ and 29.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0347] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 13.4 °^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^^21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 25.1 ^^^^ 26.1 ^^^^ and 29.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^SUHVHQW^GLVFORVXUH^ comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 25.1 ^^^^ 26.1 ^^^^ and 29.1 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0348] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 °^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^^^^^^ ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 25.1 ^^^^ 26.1 ^^^^ 29.1 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^ ^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^WKH^ present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^^^^.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 25.1 ^^^^ 26.1 ^^^^ 29.1 ^^^^ and 29.8 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0349] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or
Cooley Docket No.: STBI-081/001WO three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 17.2 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 25.1 ^^^^ 26.1 ^^^^ 29.1 ^^^^ and 29.8 ^^^^^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^FRPSRVLWLRQ^RI^ the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 17.2 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^ 20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 25.1 ^^^^ 26.1 ^^^^ 29.1 ^^^^ and 29.8 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ [0350] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more, or three or more XRPD peaks selected from the group consisting of 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 17.2 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^^20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 25.1 ^^^^ 26.1 ^^^^ 27.6 ^^^^ 29.1 ^^^^^DQG^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^,Q^VRPH^HPERGLPHQWV^^SKDUPDFHXWLFDO^ composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6 is crystalline and is characterized by XRPD peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 17.2 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^^20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 25.1 ^^^^ 26.1 ^^^^ 27.6 ^^^^ 29.1 ^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). [0351] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, or twenty-one XRPD peaks selected from those set forth in Table M^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^
Cooley Docket No.: STBI-081/001WO Table M: A representative XRPD pattern of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate polymorph Pattern 6 as shown in FIG. 15, as measured ZLWK^&X^.Į^UDGLDWLRQ^^ Gross Rel. Signal
d Net Intensity 2
-^ (°) Intensity Intensity number Value (counts) (counts) (%) Signal #1 8.2 10.83 1218.4 1356.9 86.3 Signal #2 12.3 7.17 604.7 762.0 42.8 Signal #3 13.4 6.61 262.3 441.1 18.6 Signal #4 13.9 6.35 229.6 417.8 16.3 Signal #5 14.9 5.94 553.3 751.8 39.2 Signal #6 16.7 5.29 253.0 511.7 17.9 Signal #7 17.2 5.16 154.3 428.8 10.9 Signal #8 18.4 4.82 633.2 944.9 44.9 Signal #9 19.3 4.60 1411.6 1743.2 100.0 Signal #10 20.2 4.39 1172.5 1517.9 83.1 Signal #11 20.9 4.24 331.0 682.0 23.4 Signal #12 21.7 4.09 860.6 1212.8 61.0 Signal #13 22.4 3.97 294.4 643.5 20.9 Signal #14 23.2 3.82 695.7 1035.9 49.3 Signal #15 23.8 3.74 682.1 1013.9 48.3 Signal #16 24.4 3.65 227.3 546.0 16.1 Signal #17 25.1 3.55 203.8 505.8 14.4 Signal #18 26.1 3.41 315.5 595.7 22.3 Signal #19 27.6 3.23 146.0 389.1 10.3 Signal #20 29.1 3.07 260.8 461.9 18.5 Signal #21 29.8 3.00 187.4 376.3 13.3 [0352] In some embodiments, pharmaceutical composition of the present disclosure comprises (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate polymorph Pattern 6, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate polymorph Pattern 6 is crystalline and is characterized by two or more or
Cooley Docket No.: STBI-081/001WO three or more XRPD peaks selected from those of FIG. 1^^^DV^PHDVXUHG^ZLWK^&X^.Į^ radiation. [0353] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and is non-hygroscopic. [0354] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and is solvated. [0355] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and is unsolvated. [0356] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and is anhydrous. [0357] In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate is crystalline Pattern 6 and consists essentially of (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate. Definitions [0358] Unless otherwise stated, the following terms used in the specification and claims have the following meanings set out below. [0359] As used herein, the term “subject” includes human and non-human animals, as well as cell lines, cell cultures, tissues, and organs. In some embodiments, the subject is a mammal. The mammal can be e.g., a human or appropriate non-human mammal, such as primate, mouse, rat, dog, cat, cow, horse, goat, camel, sheep or a pig. The subject can also be a bird or fowl. In some embodiments, the subject is a human. [0360] As used herein, the term “subject in need thereof” refers to a subject having a disease or having an increased risk of developing the disease. A subject in need thereof can be one who has been previously diagnosed or identified as having a disease or disorder disclosed herein. A subject in need thereof can also be one who is suffering from a disease or disorder disclosed herein. Alternatively, a subject in need thereof can be one who has an increased risk of developing such disease or disorder relative to the population at large (i.e., a subject who is predisposed to developing such disorder relative to the population at large). A subject in need thereof can have a refractory or resistant a disease or disorder disclosed herein (i.e., a disease or disorder disclosed herein that does not respond or has not yet responded to treatment). The subject may be resistant at start of treatment or may become resistant during treatment. In some embodiments, the subject in need thereof received and failed all known
Cooley Docket No.: STBI-081/001WO effective therapies for a disease or disorder disclosed herein. In some embodiments, the subject in need thereof received at least one prior therapy. [0361] As used herein, the term “treating” or “treat” describes the management and care of a patient for the purpose of combating a disease, condition, or disorder and includes the administration of a compound of the present disclosure, or a pharmaceutically acceptable salt, polymorph or solvate thereof, to alleviate the symptoms or complications of a disease, condition or disorder, or to eliminate the disease, condition or disorder. The term “treat” can also include treatment of a cell in vitro or an animal model. It is to be appreciated that references to “treating” or “treatment” include the alleviation of established symptoms of a condition. “Treating” or “treatment” of a state, disorder or condition therefore includes: (1) preventing or delaying the appearance of clinical symptoms of the state, disorder or condition developing in a human that may be afflicted with or predisposed to the state, disorder or condition but does not yet experience or display clinical or subclinical symptoms of the state, disorder or condition, (2) inhibiting the state, disorder or condition, i.e., arresting, reducing or delaying the development of the disease or a relapse thereof (in case of maintenance treatment) or at least one clinical or subclinical symptom thereof, or (3) relieving or attenuating the disease, i.e., causing regression of the state, disorder or condition or at least one of its clinical or subclinical symptoms. [0362] It is to be understood that a compound of the present disclosure, or a pharmaceutically acceptable salt, polymorph or solvate thereof, can or may also be used to prevent a relevant disease, condition or disorder, or used to identify suitable candidates for such purposes. [0363] As used herein, the term “preventing,” “prevent,” or “protecting against” describes reducing or eliminating the onset of the symptoms or complications of such disease, condition or disorder. [0364] It is to be understood that the present disclosure also provides pharmaceutical compositions comprising any compound described herein in combination with at least one pharmaceutically acceptable excipient or carrier. [0365] As used herein, the term “pharmaceutical composition” is a formulation containing the compounds of the present disclosure in a form suitable for administration to a subject. In one embodiment, the pharmaceutical composition is in bulk or in unit dosage form. The unit dosage form is any of a variety of forms, including, for example, a capsule, an IV bag, a tablet, a single pump on an aerosol inhaler or a vial. In one embodiment, the active
Cooley Docket No.: STBI-081/001WO compound is mixed under sterile conditions with a pharmaceutically acceptable carrier, and with any preservatives, buffers, or propellants that are required. [0366] As used herein, the term “pharmaceutically acceptable” refers to those compounds, anions, cations, materials, compositions, carriers, and/or dosage forms which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of human beings and animals without excessive toxicity, irritation, allergic response, or other problem or complication, commensurate with a reasonable benefit/risk ratio. [0367] As used herein, the term “pharmaceutically acceptable excipient” means an excipient that is useful in preparing a pharmaceutical composition that is generally safe, non-toxic and neither biologically nor otherwise undesirable, and includes excipient that is acceptable for veterinary use as well as human pharmaceutical use. A “pharmaceutically acceptable excipient” as used in the specification and claims includes both one and more than one such excipient. [0368] The pharmaceutical compositions containing active compounds of the present disclosure may be manufactured in a manner that is generally known, e.g., by means of conventional mixing, dissolving, granulating, dragee-making, levigating, emulsifying, encapsulating, entrapping, or lyophilising processes. Pharmaceutical compositions may be formulated in a conventional manner using one or more pharmaceutically acceptable carriers comprising excipients and/or auxiliaries that facilitate processing of the active compounds into preparations that can be used pharmaceutically. [0369] The active compounds can be prepared with pharmaceutically acceptable carriers that will protect the compound against rapid elimination from the body, such as a controlled release formulation, including implants and microencapsulated delivery systems. [0370] It is to be understood that, for the compounds of the present disclosure being capable of further forming salts, all of these forms are also contemplated within the scope of the claimed disclosure. [0371] As used herein, the term “pharmaceutically acceptable salts” refer to derivatives of the compounds of the present disclosure wherein the parent compound is modified by making acid or base salts thereof. [0372] In the salt form, it is understood that the ratio of the compound to the cation or anion of the salt can be 1:1, or any ratio other than 1:1, e.g., 3:1, 2:1, 1:2, or 1:3. [0373] It is to be understood that all references to pharmaceutically acceptable salts include solvent addition forms (solvates) or crystal forms (polymorphs) as defined herein, of the same salt.
Cooley Docket No.: STBI-081/001WO [0374] As use herein, the phrase “compound of the disclosure” refers to those compounds which are disclosed herein, both generically and specifically. [0375] It will be understood that the compounds of any one of the Formulae disclosed herein and any pharmaceutically acceptable salts thereof, comprise stereoisomers, mixtures of stereoisomers, polymorphs of all isomeric forms of said compounds. [0376] It will be understood that while compounds disclosed herein may be presented in one particular configuration. Such particular configuration is not to be construed as limiting the disclosure to one or another isomer, tautomer, regioisomer or stereoisomer, nor does it exclude mixtures of isomers, tautomers, regioisomers or stereoisomers. In some embodiments, the presentation of a compound herein in a particular configuration intends to encompass, and to refer to, each of the available isomers, tautomers, regioisomers, and VWHUHRLVRPHUV^RI^WKH^FRPSRXQG^^RU^DQ\^PL[WXUH^WKHUHRI^^ZKLOH^WKH^SUHVHQWDWLRQ^IXUWKHU^LQWHQGV^ to refer to the specific configuration of the compound. [0377] It will be understood that while compounds disclosed herein may be presented without specified configuration (e.g., without specified stereochemistry). Such presentation intends to encompass all available isomers, tautomers, regioisomers, and stereoisomers of the compound. In some embodiments, the presentation of a compound herein without specified configuration intends to refer to each of the available isomers, tautomers, regioisomers, and stereoisomers of the compound, or any mixture thereof. [0378] As used herein, the term “isomerism” means compounds that have identical molecular formulae but differ in the sequence of bonding of their atoms or in the arrangement of their atoms in space. Isomers that differ in the arrangement of their atoms in space are termed “stereoisomers.” Stereoisomers that are not mirror images of one another are termed “diastereoisomers,” and stereoisomers that are non-superimposable mirror images of each other are termed “enantiomers” or sometimes optical isomers. A mixture containing equal amounts of individual enantiomeric forms of opposite chirality is termed a “ mixture.” [0379] As used herein, the term “chiral center” refers to a carbon atom bonded to four nonidentical substituents. [0380] As used herein, the term “chiral isomer” means a compound with at least one chiral center. Compounds with more than one chiral center may exist either as an individual diastereomer or as a mixture of diastereomers, termed “diastereomeric mixture.” When one chiral center is present, a stereoisomer may be characterized by the absolute configuration (R or S) of that chiral center. Absolute configuration refers to the arrangement in space of the substituents attached to the chiral center. The substituents attached to the chiral center under
Cooley Docket No.: STBI-081/001WO consideration are ranked in accordance with the Sequence Rule of Cahn, Ingold and Prelog. (Cahn et al., Angew. Chem. Inter. Edit. ^^^^^^^^^^^^^^HUUDWD^^^^^^&DKQ^et al., Angew. Chem. ^^^^^^^^^^^^^^^&DKQ^DQG^,QJROG^^J. Chem. Soc. ^^^^^^/RQGRQ^^^^^^^^&DKQ^et al., Experientia ^^^^^^^^^^^^^^&DKQ^^J. Chem. Educ. 1964, 41, 116). [0381] As used herein, the term “geometric isomer” means the diastereomers that owe their existence to hindered rotation about double bonds or a cycloalkyl linker (e.g., 1,3- cyclobutyl). These configurations are differentiated in their names by the prefixes cis and trans, or Z and E, which indicate that the groups are on the same or opposite side of the double bond in the molecule according to the Cahn-Ingold-Prelog rules. [0382] It is to be understood that the compounds of the present disclosure may be depicted as different chiral isomers or geometric isomers. It is also to be understood that when compounds have chiral isomeric or geometric isomeric forms, all isomeric forms are intended to be included in the scope of the present disclosure, and the naming of the compounds does not exclude any isomeric forms, it being understood that not all isomers may have the same level of activity. [0383] It is to be understood that the structures and other compounds discussed in this disclosure include all atropic isomers thereof. It is also to be understood that not all atropic isomers may have the same level of activity. [0384] As used herein, the term “atropic isomers” are a type of stereoisomer in which the atoms of two isomers are arranged differently in space. Atropic isomers owe their existence to a restricted rotation caused by hindrance of rotation of large groups about a central bond. Such atropic isomers typically exist as a mixture, however as a result of recent advances in chromatography techniques, it has been possible to separate mixtures of two atropic isomers in select cases. [0385] As used herein, the term “tautomer” is one of two or more structural isomers that exist in equilibrium and is readily converted from one isomeric form to another. This conversion results in the formal migration of a hydrogen atom accompanied by a switch of adjacent conjugated double bonds. Tautomers exist as a mixture of a tautomeric set in solution. In solutions where tautomerisation is possible, a chemical equilibrium of the tautomers will be reached. The exact ratio of the tautomers depends on several factors, including temperature, solvent and pH. The concept of tautomers that are interconvertible by tautomerisations is called tautomerism. Of the various types of tautomerism that are possible, two are commonly observed. In keto-enol tautomerism a simultaneous shift of electrons and a hydrogen atom occurs. Ring-chain tautomerism arises as a result of the aldehyde group (-
Cooley Docket No.: STBI-081/001WO CHO) in a sugar chain molecule reacting with one of the hydroxy groups (-OH) in the same molecule to give it a cyclic (ring-shaped) form as exhibited by glucose. [0386] It is to be understood that the compounds of the present disclosure may be depicted as different tautomers. It should also be understood that when compounds have tautomeric forms, all tautomeric forms are intended to be included in the scope of the present disclosure, and the naming of the compounds does not exclude any tautomer form. It will be understood that certain tautomers may have a higher level of activity than others. [0387] Compounds that have the same molecular formula but differ in the nature or sequence of bonding of their atoms or the arrangement of their atoms in space are termed “isomers”. Isomers that differ in the arrangement of their atoms in space are termed “stereoisomers”. Stereoisomers that are not mirror images of one another are termed “diastereomers” and those that are non-superimposable mirror images of each other are termed “enantiomers”. When a compound has an asymmetric center, for example, it is bonded to four different groups, a pair of enantiomers is possible. An enantiomer can be characterized by the absolute configuration of its asymmetric center and is described by the R- and S-sequencing rules of Cahn and Prelog, or by the manner in which the molecule rotates the plane of polarised light and designated as dextrorotatory or levorotatory (i.e., as (+) or (-)-isomers respectively). A chiral compound can exist as either individual enantiomer or as a mixture thereof. A mixture containing equal proportions of the enantiomers is called a “ mixture”. [0388] The compounds of this disclosure may possess one or more asymmetric centerV^^VXFK^ compounds can therefore be produced as individual (R)- or (S)-stereoisomers or as mixtures thereof. Unless indicated otherwise, the description or naming of a particular compound in the specification and claims is intended to include both individual enantiomers and mixtures, or otherwise, thereof. The methods for the determination of stereochemistry and the separation of stereoisomers are well-known in the art (see discussion in Chapter 4 of “Advanced Organic Chemistry”, 4th edition J. March, John Wiley and Sons, New York, 2001), for example by synthesis from optically active starting materials or by resolution of a form. Some of the compounds of the disclosure may have geometric isomeric centers (E- and Z- isomers). It is to be understood that the present disclosure encompasses all optical, diastereoisomers and geometric isomers and mixtures thereof that possess inflammasome inhibitory activity. [0389] The present disclosure also encompasses compounds of the disclosure as defined herein which comprise one or more isotopic substitutions.
Cooley Docket No.: STBI-081/001WO Biological Assays [0390] Compounds designed, selected and/or optimized by methods described above, once produced, can be characterized using a variety of assays known to those skilled in the art to determine whether the compounds have biological activity. For example, the molecules can be characterized by conventional assays, including but not limited to those assays described below, to determine whether they have a predicted activity, binding activity and/or binding specificity. [0391] Furthermore, high-throughput screening can be used to speed up analysis using such assays. As a result, it can be possible to rapidly screen the molecules described herein for activity, using techniques known in the art. General methodologies for performing high- throughput screening are described, for example, in Devlin (1998) High Throughput Screening, Marcel DekNHU^^DQG^8^6^^3DWHQW^1R^^^^^^^^^^^^ High-throughput assays can use one or more different assay techniques including, but not limited to, those described below. [0392] Various in vitro or in vivo biological assays may be suitable for detecting the effect of the compounds of the present disclosure. These in vitro or in vivo biological assays can include, but are not limited to, enzymatic activity assays, electrophoretic mobility shift assays, reporter gene assays, in vitro cell viability assays, and the assays described herein. [0393] In some embodiments, the biological assay is described in the Examples herein. EMBODIMENTS [0394] Embodiment 1. A pharmaceutical composition comprising (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine, or a pharmaceutically acceptable salt thereof, and an excipient. [0395] Embodiment 2. The pharmaceutical composition of embodiment 1, comprising (R)- 1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine free base. [0396] Embodiment 3. The pharmaceutical composition of embodiment 1, comprising a pharmaceutically acceptable salt of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine. [0397] Embodiment 4. The pharmaceutical composition of embodiment 1 or 3, wherein the pharmaceutically acceptable salt is a fumarate salt. [0398] Embodiment 4a. The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt polymorphic Form A, Form B, Form I, Form II, Pattern 3a, Pattern 5, Pattern 6, or mixtures thereof.
Cooley Docket No.: STBI-081/001WO [0399] Embodiment 4b. The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a monofumarate salt polymorphic Form A, Form B, or a mixture thereof. [0400] Embodiment 4c. The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a substantially pure monofumarate salt polymorphic Form A. [0401] Embodiment 4d. The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a monofumarate salt and comprises a mixture of polymorphic Form A and Form B. [0402] Embodiment 4d’. The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt and comprises a mixture of polymorphic Form A and Form I. [0403] Embodiment 4d’’. The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt comprises a mixture of polymorphic Form A and Form II. [0404] Embodiment 4d’’’. The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt comprises a mixture of polymorphic Form A and Pattern 3a. [0405] Embodiment 4d’’’’. The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt comprises a mixture of polymorphic Form A and Pattern 5. [0406] Embodiment 4d’’’’’. The pharmaceutical composition of any one of the previous embodiments, wherein the pharmaceutically acceptable salt is a fumarate salt comprises a mixture of polymorphic Form A and Pattern 6. [0407] Embodiment 4e. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate has an XRPD with representative peaks at 22.5°±0.2° 2-Theta, 16.0°±0.2° 2-Theta, and 14.1°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0408] Embodiment 4f. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate has an XRPD with representative peaks at 19.3°±0.2° 2-Theta, 21.4°±0.2° 2-Theta, and 22.3°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^ [0409] Embodiment 4g. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate
Cooley Docket No.: STBI-081/001WO has an XRPD with representative peaks at 14.0°±0.2° 2-Theta, 15.9°±0.2° 2-Theta, and 22.3°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^ [0410] Embodiment 4h. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate has an XRPD with representative peaks at 19.3°±0.2° 2-Theta, 19.6°±0.2° 2-Theta, and 22.6°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0411] Embodiment 4i. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate has an XRPD with representative peaks at 16.1°±0.2° 2-Theta, 21.6°±0.2° 2-Theta, and 22.6°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0412] Embodiment 4j. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate has an XRPD with representative peaks at 17.6°±0.2° 2-Theta, 19.4°±0.2° 2-Theta, and 23.5°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0413] Embodiment 4k. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate has an XRPD with representative peaks at 17.8°±0.2° 2-Theta, 19.5°±0.2° 2-Theta, and 20.3°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0414] Embodiment 4l. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate has an XRPD with representative peaks at 15.9°±0.2° 2-Theta, 19.4°±0.2° 2-Theta, and 21.0°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0415] Embodiment 4m. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate has an XRPD with representative peaks at 16.0°±0.2° 2-Theta, 21.2°±0.2° 2-Theta, and 27.2°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0416] Embodiment 4n. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate has an XRPD with representative peaks at 15.8°±0.2° 2-Theta, 20.9°±0.2° 2-Theta, and 26.9°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0417] Embodiment 4o. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate has an XRPD with representative peaks at 17.9°±0.2° 2-Theta, 19.7°±0.2° 2-Theta, and 23.9°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^
Cooley Docket No.: STBI-081/001WO [0418] Embodiment 4p. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate has an XRPD with representative peaks at 18.1°±0.2° 2-Theta, 19.8°±0.2° 2-Theta, and 19.9°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0419] Embodiment 4q. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate has an XRPD with representative peaks at 7.9°±0.2° 2-Theta, 20.2°±0.2° 2-Theta, and 21.6°±0.2° 2-Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0420] Embodiment 4r. The pharmaceutical composition of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate has an XRPD with representative peaks at 8.2°±0.2° 2-Theta, 19.3°±0.2° 2-Theta, and 20.2°±0.2° 2- Theta, as measured with Cu KĮ^UDGLDWLRQ^^^ [0421] Embodiment 4s. The pharmaceutical composition of any one of the previous embodiments, wherein the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate is a substantially pure monofumarate salt polymorphic Form A. [0422] Embodiment 5a. The pharmaceutical composition of any one of embodiments 1-4, wherein the excipient comprises a filler, a binder, a glidant, a lubricant, a disintegrant, and/or a plasticizer. [0423] Embodiment 5b. The pharmaceutical composition of any one of embodiments 1-4, wherein the excipient comprises a filler, a binder, a glidant, a lubricant, a disintegrant, and a plasticizer. [0424] Embodiment 6a. The pharmaceutical composition of embodiment 5, wherein the filler is selected from the group consisting of lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, silicified microcrystalline cellulose, and maltose, and a combination thereof. [0425] Embodiment 6b. The pharmaceutical composition of embodiment 5, wherein the filler comprises lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, silicified microcrystalline cellulose, or maltose, or combinations thereof. [0426] Embodiment 7a. The pharmaceutical composition of embodiment 5, wherein the binder is selected from the group consisting of povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, ethyl cellulose, and PEO 1NF, and a combination thereof.
Cooley Docket No.: STBI-081/001WO [0427] Embodiment 7b. The pharmaceutical composition of embodiment 5, wherein the binder comprises povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, ethyl cellulose, or PEO 1NF, or combinations thereof. [0428] Embodiment 8a. The pharmaceutical composition of embodiment 5, wherein the glidant is selected from the group consisting of talc and colloidal silicon dioxide, and a combination thereof. [0429] Embodiment 8b. The pharmaceutical composition of embodiment 5, wherein the glidant comprises talc, colloidal silicon dioxide, or a combination thereof. [0430] Embodiment 9a. The pharmaceutical composition of embodiment 5, wherein the lubricant is selected from the group consisting of magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, and PEO 1NF, and a combination thereof. [0431] Embodiment 9b. The pharmaceutical composition of embodiment 5, wherein the lubricant comprises magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, or PEO 1NF, or combinations thereof. [0432] Embodiment 10a. The pharmaceutical composition of embodiment 5, wherein the disintegrant is selected from the group consisting of sodium starch glycolate, croscarmellose sodium, polyplasdone, and L-HPC, and a combination thereof. [0433] Embodiment 10b. The pharmaceutical composition of embodiment 5, wherein the disintegrant comprises sodium starch glycolate, croscarmellose sodium, polyplasdone, and L- HPC, or combinations thereof. [0434] Embodiment 11. The pharmaceutical composition of embodiment 5, wherein the plasticizer comprises polyethylene glycol. [0435] Embodiment 12. The pharmaceutical composition of any one of embodiments 1-4, wherein the excipient is selected from lactose monohydrate, maize starch, Neusilin UFL2, microcrystalline cellulose, dicalcium phosphate, mannitol, PROSOLV® EASYtab Nutra CM, isomalt, povidone, hydroxypropyl cellulose, hypromellose, dextrates, sodium carboxy methyl cellulose, alginic acid, talc, colloidal silicon dioxide, magnesium stearate, sodium stearyl fumarate, hydrogenated vegetable oil, stearic acid, sodium starch glycolate, croscarmellose sodium, polyplasdone, L-HPC, Opadry, ethyl cellulose, silicified microcrystalline cellulose, maltose, polyethylene glycol, PEO 1NF, and methacrylic acid copolymer, and a combination thereof. [0436] Embodiment 13. The pharmaceutical composition of any one of embodiments 1-12, further comprising a film coating.
Cooley Docket No.: STBI-081/001WO [0437] Embodiment 14. The pharmaceutical composition of 13, wherein the film coating comprises Opadry. [0438] Embodiment 15. The pharmaceutical composition of any one of embodiments 1-14, further comprising a release controlling polymer. [0439] Embodiment 16a. The pharmaceutical composition of 15, wherein the release controlling polymer is selected from the group consisting of hypromellose, ethyl cellulose, and methacrylic acid copolymer, and a combination thereof. [0440] Embodiment 16b. The pharmaceutical composition of 15, wherein the release controlling polymer comprises hypromellose, ethyl cellulose, or methacrylic acid copolymer, or combinations thereof. [0441] Embodiment 17. The pharmaceutical composition of any one of embodiments 1-16, further comprising a capsule shell. [0442] Embodiment 18a. The pharmaceutical composition of 15, wherein the capsule shell is an HPMC capsule shell. [0443] Embodiment 18b. The pharmaceutical composition of 15, wherein the capsule shell comprises an HPMC capsule or a gelatin capsule shell. [0444] Embodiment 19. A method of treating or preventing a disease or condition, comprising administering to a subject in need thereof an effective amount of the pharmaceutical composition of any one of embodiments 1-18. [0445] Embodiment 20. A pharmaceutical composition of any one of embodiments 1-18 for use in the treatment or prevention of a disease or condition. [0446] Embodiment 21. Use of the pharmaceutical composition of any one of embodiments 1-18 in the manufacture of a medicament for the treatment or prevention of a disease or condition. [0447] Embodiment 22. The pharmaceutical composition according to any one of the previous embodiments, wherein the pharmaceutical composition does not comprise a gelatin capsule. [0448] Embodiment 23. The pharmaceutical composition according to any one of the previous embodiments, wherein the pharmaceutical composition does not comprise high moisture containing excipients. EXAMPLES
Cooley Docket No.: STBI-081/001WO [0449] Methods for preparing crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate are disclosed in PCT/US2022/079993, which is incorporated by reference herein in its entirety for all purposes. [0450] Example 1. Synthesis of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine fumarate salt [0451] $^VROXWLRQ^RI^>^^5^^^^^^^PHWKR[\^^+^LQGRO^^^\O^SURSDQ^^^\O@GLPHWK\ODPLQH^^^^^^^J^ 30.7 mmol) in chloroform (50 mL) was added to a boiling solution of fumaric acid (3.57 g, 30.7 mmol) in THF (150 mL). The solution was then concentrated in vacuo to a viscous brown oil. This material was dissolved in methyl ethyl ketone, also known as 2-butanone ^0(.^^^^^P/^^^ZLWK^VRQLFDWLRQ^^DQG^WR^WKH^VWLUULQJ^VROXWLRQ^ZDV^DGGHG^FU\VWDOV^^FD^^^^^PJ^^RI^ >^^5^^^^^^^^PHWKR[\^^+^LQGRO^^^\O^SURSDQ^^^\O@GLPHWK\ODPLQH^IXPDUDWH^VDOW^^SRO\PRUSK^ form A). A fine precipitate was observed after 10 min. The suspension was stirred for 24 hours at rt. The solid was isolated by filtration and the filter cake was washed with MEK (ca. 5 mL). The salt was air dried on the filter for 20 min and then dried in a vacuum oven over a weekend at 40 °C. The title compound was obtained as an off-white solid (8.1 g, 75%). 5HWHQWLRQ^WLPH^^^^^^^PLQXWHV^^3XULW\^E\^89^^^^^^QP^^^- ^^^^ ^^^^^^&DOFXODWHG^IRU^ >&^^+^^1^2@^^^^^^^^^IRXQG^^^^^^^^^+^105^^^^^^0+]^^'062-G^^^į^^^^^^^G^^-^ ^^^^^+]^^ 1H), 7.29 (d, J = 3.0 Hz, 1H), 7.03 (d, J = 2.4 Hz, 1H), 6.76 (dd, J = 8.9, 2.5 Hz, 1H), 6.60 (s, 2H), 6.32 (dd, J = 3.1, 0.8 Hz, 1H), 4.23 (dd, J = 14.2, 6.4 Hz, 1H), 4.00 (dd, J = 14.2, 7.7 Hz, 1H), 3.75 (s, 3H), 3.07 (dt, J = 7.6, 6.4 Hz, 1H), 2.27 (s, 6H), 0.84 (d, J = 6.6 Hz, 3H). XRPD analysis showed that this material was crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A (FIGs. 5 – sample 1, and FIG. 6 – sample 2), as the XRPD profile corresponded to the representative XRPD pattern for (R)-1-(5-methoxy- 1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A that is characterized in FIG. 2, and Table B. XRPD peaks shown in FIG. 5 are presented in the table below. Signal Position. d
-spacing >c Relative No.
>^^^@ @ Intensity >^@ 1 10.2118 8.65535 18.19 2 13.4987 6.55428 43.98 3 14.1419 6.25761 55.37 4 15.6865 5.64474 21.11 5 16.0097 5.5315 67.09 6 18.5332 4.78363 19.71 7 19.0629 4.65188 21.73 8 19.526 4.54259 41.34
Cooley Docket No.: STBI-081/001WO 9 20.9831 4.2303 27.12 10 21.3971 4.14939 29.15 11 21.6587 4.09986 36.3 12 22.4904 3.95009 100 13 23.2901 3.81622 12.15 14 24.5427 3.62422 10.23 15 25.1714 3.53511 10.3 16 28.2412 3.15743 15.82 17 29.1829 3.05765 13.51 [0452] The 2-Theta peak values that are provided for the XRPD are within ±0.2° 2-Theta. [0453] XRPD peaks shown in FIG. 6 are presented in the table below. Signal Position d-spacing >c@ Relative No. >^^^@ Intensity >^@ 1 10.2121 8.65507 17.73 2 13.5021 6.55265 41.1 3 14.1435 6.25689 50.24 4 15.7017 5.63931 20.51 5 16.0141 5.52998 64.28 6 18.5312 4.78413 19.76 7 19.0784 4.64812 22.95 8 19.5294 4.54179 35.8 9 20.9861 4.22971 27.92 10 21.4019 4.14847 29.07 11 21.6681 4.09811 33.8 12 22.4888 3.95036 100 13 23.2878 3.81661 13.57 14 24.5339 3.6255 10.59 15 25.1566 3.53715 13.37 16 28.2376 3.15782 16.44 17 29.1788 3.05808 14.71 [0454] The 2-Theta peak values that are provided for the XRPD are within ±0.2° 2-Theta. In some embodiments, (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate is characterized as having an XRPD with representative peaks at 22.5 ^^^^^16.0 ^^^^^ and 14.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, (R)- 1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate is characterized as having an XRPD with representative peaks at 22.5 ^^^^^16.0 ^^^^^14.1 ^^^, 13.5 ^^^, and 19.5 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^
Cooley Docket No.: STBI-081/001WO Example 2. Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Fumarate, Forms A, B, I, II, Pattern 3a, Pattern 5, Pattern 6 [0455] Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Forms A, B, I, II, Pattern 3a, Pattern 5, and Pattern 6 were prepared according to PCT/US2022/079993, which is incorporated by reference herein in its entirety for all purposes. Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Monofumarate, Form A [0456] In some embodiments, the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate is Form A. [0457] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 1. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising characteristic peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern further comprising one or more peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 22.3 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising one or more peaks selected from those set forth in Table A, DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ [0458] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 2. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising characteristic peaks at 14.0 ^^^^ 15.9 ^^^^ and 22.3 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern further comprising one or more peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^
Cooley Docket No.: STBI-081/001WO radiation). In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising one or more peaks selected from those set forth in Table B^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ [0459] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 3. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising characteristic peaks at 19.3 ^^^^ 19.6 ^^^^ and 22.6 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern further comprising one or more peaks at ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^^In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising one or more peaks selected from those set forth in Table C, as measured ZLWK^&X^.Į^UDGLDWLRQ^ [0460] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 4. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising characteristic peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form A has a XRPD pattern further comprising one or more peaks DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form A has a XRPD pattern comprising one or more peaks selected from those set forth in Table D^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Monofumarate, Form B
Cooley Docket No.: STBI-081/001WO [0461] In some embodiments, the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate is Form B. [0462] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form B has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 7. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern comprising characteristic peaks at 17.8 ^^^^ 19.5 ^^^^ and 20.3 ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern further comprising one or more peaks at 5.9 ^^^^ 9.5 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.8 ^^^^ 19.5 ^^^^ 20.3 ^^^^ 23.6 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^ radiation). In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form B has a XRPD pattern comprising one or more peaks selected from those set forth in Table E, DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ [0463] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine monofumarate Form B has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 8. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern comprising characteristic peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^ ^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern further comprising one or more peaks at DW^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^DQG^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine monofumarate Form B has a XRPD pattern comprising one or more peaks selected from those set forth in Table F, as PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Hemi-fumarate, Form I and Form II Production of the Hemi-fumarate Salt [0464] This example describes the production of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate. (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate and free base compound in equimolar amounts were
Cooley Docket No.: STBI-081/001WO dissolved in 10 vol methanol with heating. The resultant solution was concentrated to dryness and the solid residue was analyzed by 1H NMR, XRPD and DSC. This sample comprised crystalline material Form I, as illustrated in FIG. 9. [0465] Hemi-fumarate prepared according to the method above was suspended in MTBE and stirred, yielding, following isolation via centrifugation and drying, crystalline hemi- fumarate of Form II as illustrated in FIG. 11. Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Hemi-fumarate, Form I [0466] In some embodiments, the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate is Form I. [0467] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate Form I has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 9. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern comprising characteristic peaks at 15.9 ^^^^ 19.4 ^^^^ and 21.0 ^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern further comprising one or more peaks at 11.7 ^^^^ 13.4 ^^^^ 13.7 ^^^^ 15.2 ^^^^ 15.9 ^^^^ 18.9 ^^^^ 19.4 ^^^^ 21.0 ^^^^ 21.6 ^^^^ 22.5 ^^^^ 23.2 ^^^^ and 27.1 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^ In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern comprising one or more peaks selected from those set forth in Table G^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ [0468] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate Form I has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 10. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern comprising characteristic peaks at 16.0 ^^^^ 21.2 ^^^^ and 27.2 ^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD pattern further comprising one or more peaks at 11.8 ^^^^ 13.7 ^^^^ 15.4 ^^^^ 16.0 ^^^^ 19.2 ^^^^ 19.5 ^^^^ 21.2 ^^^^ 21.7 ^^^^ 22.6 ^^^^ 23.4 ^^^^^24.3 ^^^^ 25.0 ^^^^ 27.2 ^^^^ 28.5 ^^^^ and 30.4 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form I has a XRPD
Cooley Docket No.: STBI-081/001WO pattern comprising one or more peaks selected from those set forth in Table H, as measured ZLWK^&X^.Į^UDGLDWLRQ^ Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Hemi-fumarate, Form II [0469] In some embodiments, the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate is Form II. [0470] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine hemi-fumarate Form II has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 11. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II has a XRPD pattern comprising characteristic peaks at ^^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^ ^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II has a XRPD pattern further comprising one or more peaks at 11.5 ^^^^ 13.3 ^^^^ 13.5 ^^^^ 15.1 ^^^^ 15.8 ^^^^ 18.8 ^^^^ 19.2 ^^^^ 20.9 ^^^^ 21.4 ^^^^ 22.4 ^^^^^23.1 ^^^^ 24.0 ^^^^ 24.7 ^^^^ 26.9 ^^^^ 28.2 ^^^^ and 30.2 ^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine hemi-fumarate Form II has a XRPD pattern comprising one or more peaks selected from those set forth in Table I^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Fumarate, Pattern 3a [0471] In some embodiments, the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate is Pattern 3a. [0472] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Pattern 3a has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 12. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern comprising characteristic peaks at ^^^^^^^^^^^^^^ ^^^^^DQG^^^^^^^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern further comprising one or more peaks at 9.6 ^^^^ 13.9 ^^^^ 15.2 ^^^^ 16.9 ^^^^ 17.9 ^^^^ 19.7 ^^^^ 20.5 ^^^^ 23.9 ^^^^ 24.9 ^^^^ 25.2 ^^^^ 28.5 ^^^^ and 29.8 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^ &X^.Į^^UDGLDWLRQ^^ In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-
Cooley Docket No.: STBI-081/001WO dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern comprising one or more peaks selected from those set forth in Table J^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ [0473] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Pattern 3a has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 13. In some embodiments, crystalline (R)-1- (5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern comprising characteristic peaks at 18.1 ^^^^ 19.8 ^^^^ and 19.9 ^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern further comprising one or more peaks at 9.5 ^^^^ 11.9 ^^^^ 14.1 ^^^^ 15.1 ^^^^ 16.8 ^^^^ 17.6 ^^^^ 18.1 ^^^^ 19.0 ^^^^ 19.8 ^^^^ 19.9 ^^^^^23.6 ^^^^^24.0 ^^^^^25.7 ^^^^ 28.3 ^^^^ 30.0 ^^^^ and 31.7 ^^^ ^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 3a has a XRPD pattern comprising one or more peaks selected from those set forth in Table K, DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Fumarate, Pattern 5 [0474] In some embodiments, the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate is Pattern 5. [0475] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Pattern 5 has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 14. In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5 has a XRPD pattern comprising characteristic peaks at 7.9 ^^^^ 20.2 ^^^, and 21.6 ^^^ ^^^^^^^^^^^^^^^^ ^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5 has a XRPD pattern further comprising one or more peaks at 7.9 ^^^^ 15.7 ^^^^ 20.2 ^^^^ 21.6 ^^^^ and 23.7 ^^^^^^^^^^ ^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^^ In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 5 has a XRPD pattern comprising one or more peaks selected from those set forth in Table L, as measured ZLWK^&X^.Į^UDGLDWLRQ^ Crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Fumarate, Pattern 6
Cooley Docket No.: STBI-081/001WO [0476] In some embodiments, the crystalline form of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate is Pattern 6. [0477] In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Pattern 6 has an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 15. In some embodiments, crystalline (R)-1-(5- methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 6 has a XRPD pattern comprising characteristic peaks at ^^^^^^^^^^^^^^^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ RU^^^^^^^^^^^&X^.Į^^UDGLDWLRQ^. In some embodiments, crystalline (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine fumarate Pattern 6 has a XRPD pattern further comprising one or more peaks at 8.2 ^^^^ 12.3 ^^^^ 13.4 ^^^^ 13.9 ^^^^ 14.9 ^^^^ 16.7 ^^^^ 17.2 ^^^^ 18.4 ^^^^ 19.3 ^^^^ 20.2 ^^^^^20.9 ^^^^ 21.7 ^^^^ 22.4 ^^^^ 23.2 ^^^^ 23.8 ^^^^ 24.4 ^^^^ 25.1 ^^^^ 26.1 ^^^^ 27.6 ^^^^ 29.1 ^^^^^DQG^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^RU^^^^^^^^^^^&X^ .Į^^UDGLDWLRQ^^In some embodiments, crystalline (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Pattern 6 has a XRPD pattern comprising one or more peaks selected from those set forth in Table M^^DV^PHDVXUHG^ZLWK^&X^.Į^UDGLDWLRQ^ Example 3. Excipient Compatibility of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine Fumarate (Form A) [0478] Compatibility for (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine Fumarate (Form A) as prepared in Example 1 (hereafter Active Pharmaceutical Ingredient, or API) with different category of excipients using drug and excipient binary mixtures were studied and reported. Selection of compatible excipients was based on visual appearance, and impurities of drug-excipient mixtures at specified stability time points. Results for the initial, 15-day and 30-day time points at 40°C/75%RH are presented here. [0479] Binary mixtures of 50% excipient and 50% API (equivalent to 1:1 excipient ratio) was made and then exposed to elevated temperature and humidity conditions. The samples were analyzed for evidence of API degradation or other adverse change. [0480] The analytical conditions for the assay/related substances determination are given in Table 1. Table 1: Assay and Related Substances Chromatographic Conditions C
olumn Kinetex PS C182.6μm 100 x 4.6mm Guard column/ cartridge (Optional) TBC Column Oven 40°C Injection Volume 2.0μL
Cooley Docket No.: STBI-081/001WO Autosampler Temperature Ambient Flow Rate 1.0 mL/min Detection UV 236 nm, ~2.5Hz Spectra (optional, see protocol) 200 to 400nm, ~1nm step Mobile Phase A 95:5 water:methanol + 0.2% H
3PO
4 Mobile Phase B 25:75 water:methanol + 0.2% H
3PO
4 Time, %A %B min 0.0 100.0 0.0 2.0 100.0 0.0 Gradient Program 29.5 13.0 87.0 31.0 13.0 87.0 31.1 100.0 0.0 37.0 100.0 0.0 Needle Wash Diluent Run Time 37 minutes Samples 1mg/mL in Mobile Phase A Standards 1mg/mL API in Mobile Phase A [0481] Samples were stored in glass vials at the conditions listed in Table 2. Samples were tested for assay, related substances, and physical appearance before storage (T0) and after 15 days and 30 days at 40°C/75%RH. [0482] Table 2: Storage Condition Sample Details Storage C
ondition 40°C / 75% RH Number T
ime Sample details Initial 25°C/60%RH* of p
oint 15days 30days samples S
r. No (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine F
umarate 1 API 1 1 1 1 04 2
Individual E
xcipient 31 31 31 93 3 Excipient + API 33 33 33 33 132 Total samples 229 * Analysis to be performed if any significant change observed in 40ºC/75%RH [0483] The following excipients were tested. Table 3: Excipients for Compatibility Testing of (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine fumarate Sr. N
o Excipient/substrate Grade Function 1
(R)-1-(5-methoxy-1H-indol-1- -- API yl)-N,N-dimethylpropan-2- amine fumarate (Form A) 2
Lactose monohydrate -- Filler
Cooley Docket No.: STBI-081/001WO 3
Maize starch StarTab Filler 4 Neusilin UFL2 UFL2 Filler 5 Microcrystalline cellulose -- Filler 6 Dicalcium Phosphate Filler 7 Mannitol Pearlitol 200 SD Filler 8 PROSOLV® EASYtab Nutra Filler CM 9
Isomalt Galen IQ 721 Filler 10 Povidone Kollidon K30 Binder 11 Hydroxypropyl cellulose Klucel EXF Binder 12 Hypromellose -- Binder and Release controlling polymer 1
3 Dextrates -- Binder 14 Sodium Carboxy Methyl -- Binder Cellulose 1
5 Alginic Acid -- Binder 16 Talc -- Glidant 17 Colloidal silicon dioxide Aerosil 200 Glidant 18 Magnesium stearate Ligamed MF2V Lubricant 19 Sodium Stearyl Fumarate EP/NF/PRUV Lubricant 20 Hydrogenated Vegetable Oil LUBRITAB Lubricant 21 Stearic Acid -- Lubricant 22 Sodium starch glycolate -- Disintegrants 23 Croscarmellose sodium -- Disintegrants 24 Polyplasdone --- Disintegrants 25 L-HPC -- Disintegrants 26 Opadry -- Film coating 27 API+ HPMC capsule shell -- Capsule shell 28 API+ Gelatin capsule shell -- Capsule shell 29 Ethyl cellulose -- Binder and Release controlling polymer 30 Silicified microcrystalline -- Filler cellulose 3
1 Maltose -- Filler 32 Polyethylene Glycol -- Plasticizer 33 PEO 1NF -- Binder/Lubricants 34 Methacrylic acid copolymer -- Release controlling polymer [0484] The API was mixed with an excess of excipient to detect a potential incompatibility with the highest probability. The dry mixtures were prepared by weighing using a balance,
Cooley Docket No.: STBI-081/001WO followed by gentle mixing using a spatula in transparent glass vials. Binary mixture of API with selected excipient were prepared. Compatibility of the binary mixture of 50% excipient and 50% API which is equivalent to 1:1 excipient ratio. Samples were prepared and packed in glass vials with cap. These vials were kept at stress condition of 40°C±2 /75% RH±5 for period of 15 and 30 days in closed condition. Besides the storage of drug-excipient mixtures, the pure drug substance was also be used as a reference in the compatibility studies at all storage conditions. Also, the pure excipients were stored at all storage conditions and analyzed along with the binary mixture. [0485] Interpretations/ Acceptance criteria: Results of 40°C/75%RH conditions were compared with the initial samples and the results were interpreted for the incompatibility. Any significant change with respect to initial time point was considered as an indication of incompatibility. The study results will be used for the development of the drug product. Results Analytical Method Establishment Generic chromatographic conditions had already been developed that chromatographed a wide range of compounds. To confirm these were suitable for this (R)-1-(5-methoxy-1H- indol-1-yl)-N,N-dimethylpropan-2-amine API a 1mg/mL solution was prepared in diluent/mobile phase A (95:5 water:Methanol + 0.2% phosphoric acid). The API dissolved readily under these conditions confirming that the diluent was suitable. This solution was injected on the HPLC over a range of injection volumes (0.5μ to 5.0μl) to establish which injection volume gives an appropriate main peak response and sensitivity for any related substances peaks without compromising peak shape. Spectral data was also collected to confirm an appropriate wavelength for the data to be collected at. Examining the UV spectrum collected confirmed that 220nm was an appropriate wavelength (see Figure 16). There is a strong absorbance and a plateau in the spectra at this wavelength. (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine was found to give a linear response at this wavelength over the range of injection volumes made (see Figure 17). An injection volume of 2.0μl gave a good peak response (height ~0.9AU) while keeping the main peak narrow and no obvious loss of resolution. The main peak tailing was higher than is normally accepted (USP Tailing 2.2) but given there was no loss of resolution and accurate integration of the main peak was still possible (see Figure 18 & 19). The peak shape for any
Cooley Docket No.: STBI-081/001WO related substances peaks observed in the chromatogram was good and therefore this was deemed acceptable. Physical Appearance [0486] No obvious visual changes in any of the samples were observed when stored for up to 30 days at 40°C/75RH (Table 4). Table 4: Appearance of Samples ((R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2- amine: Excipients) Sr. E
xcipient/substrate Initi 15 days 30 days N
o al 40°C/75%RH 40°C/75%RH (R)-1-(5-methoxy-1H-indol- No ch -2- White to off-whi ange No change 1 1-yl)-N,N-dimethylpropan te po from initial from initial amine Fumarate (Form A) wder. timepoint. timepoint. Lactose monohydrate White to off-white No change No change 2 powder. from initial from initial timepoint. timepoint. Maize starch White to off-white No change No change 3 powder. from initial from initial timepoint. timepoint. Neusilin UFL2 White to off-white No change No change 4 powder. from initial from initial timepoint. timepoint. Microcrystalline cellulose White to off-white No change No change 5 powder. from initial from initial timepoint. timepoint. Dicalcium Phosphate White to off-white No change No change 6 powder. from initial from initial timepoint. timepoint. Mannitol White to off-white No change No change 7 powder. from initial from initial timepoint. timepoint. PROSOLV® EASYtab White to off-white No change No change 8 Nutra CM powder. from initial from initial timepoint. timepoint. Isomalt White to off-white No change No change 9 powder. from initial from initial timepoint. timepoint. Povidone White to off-white No change No change 10 powder. from initial from initial timepoint. timepoint. Hydroxypropyl cellulose White to off-white No change No change 11 powder. from initial from initial timepoint. timepoint. Hypromellose White to off-white No change No change 12 powder. from initial from initial timepoint. timepoint. Dextrates White to off-white No change No change 13 powder. from initial from initial timepoint. timepoint.
Cooley Docket No.: STBI-081/001WO Sr. E
xcipient/su 15 days 30 days
No bstrate Initial 40°C/75%RH 40°C/75%RH Sodium Carboxy Methyl White to off-white No change No change 14 Cellulose powder. from initial from initial timepoint. timepoint. Alginic Acid White to off-white No change No change 15 powder. from initial from initial timepoint. timepoint. Talc White to off-white No change No change 16 powder. from initial from initial timepoint. timepoint. Colloidal silicon dioxide White to off-white No change No change 17 powder. from initial from initial timepoint. timepoint. Magnesium stearate White to off-white No change No change 18 powder. from initial from initial timepoint. timepoint. Sodium Stearyl Fumarate White to off-white No change No change 19 powder. from initial from initial timepoint. timepoint. Hydrogenated Vegetable Oil White to off-white No change No change 20 powder. from initial from initial timepoint. timepoint. Stearic Acid White to off-white No change No change 21 powder. from initial from initial timepoint. timepoint. Sodium starch glycolate White to off-white No change No change 22 powder. from initial from initial timepoint. timepoint. Croscarmellose sodium White to off-white No change No change 23 powder. from initial from initial timepoint. timepoint. Polyplasdone White to off-white No change No change 24 powder. from initial from initial timepoint. timepoint. L-HPC White to off-white No change No change 25 powder. from initial from initial timepoint. timepoint. Opadry White to off-white No change No change 26 powder. from initial from initial timepoint. timepoint. API+ HPMC capsule shell White to off-white No change No change 27 powder in a white from initial from initial capsule. timepoint. timepoint. API+ Gelatin capsule shell White to off-white No change No change 28 powder in a white from initial from initial capsule. timepoint. timepoint. Ethyl cellulose White to off-white No change No change 29 powder. from initial from initial timepoint. timepoint. Silicified microcrystalline White to off-white No change No change 30 cellulose powder. from initial from initial timepoint. timepoint.
Cooley Docket No.: STBI-081/001WO Sr. E
xci 15 days 30 days N
o pient/substrate Initial 40°C/75%RH 40°C/75%RH Maltose White to off-white No change No change 31 powder. from initial from initial timepoint. timepoint. 32 Polyethylene Glycol White to off-white No change No change powder. from initial from initial timepoint. timepoint. 33 PEO 1NF White to off-white No change No change powder. from initial from initial timepoint. timepoint. 34 Methacrylic acid copolymer White to off-white No change No change powder. from initial from initial timepoint. timepoint. [0487] No obvious changes in any of the related substances peaks were observed for the majority of the (R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine samples when stored for 15 days and 30 days at 40°C/75%RH (Table 5). [0488] A larger increase in total % impurities is seen in the Methacrylic acid copolymer and Hypromellose sample where there is also an increase in the peak at approximately RRT 1.8. An example T30 day API chromatogram is shows in Figure 20. [0489] The results observed suggest that caution should be taken when using either Methacrylic acid copolymer and Hypromellose with (R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine API. Table 5. Total impurities (Area%) of Samples ((R)-1-(5-methoxy-1H-indol-1-yl)-N,N- dimethylpropan-2-amine: Excipients) S
r. No Excipient/ substrate Initial 15 days 30 days 4
0°C/75%RH 40°C/75%RH (R)-1-(5-methoxy-1H-indol-1- 1 yl)-N,N-dimethylpropan-2- 1.66 1.62 1.55 amine Fumarate (Form A) 2 Lactose monohydrate 1.70 1.62 1.61 3 Maize starch 1.72 1.65 1.63 4 Neusilin UFL2 1.66 1.61 1.91 5 Microcrystalline cellulose
1.74 1.69 1.68 6 Dicalcium Phosphate 1.67 1.65 1.71 7 Mannitol 1.71 1.75 1.72 8
PROSOLV® EASYtab Nutra C
M 1.66 1.76 1.63 9 Isomalt 0.73 1.68 1.61 10 Povidone 1.67 1.67 1.81 11 Hydroxypropyl cellulose
1.65 1.58 1.58
Cooley Docket No.: STBI-081/001WO S
r. No Excipient/ substrate Initial 15 days 30 days 4
0°C/75%RH 40°C/75%RH (R)-1-(5-methoxy-1H-indol-1- 1 yl)-N,N-dimethylpropan-2- 1.66 1.62 1.55 amine Fumarate (Form A) 12 Hypromellose 2.01 1.91 4.19 13 Dextrates 1.76 1.64 1.59 1
4 Sodium Carboxy Methyl C
ellulose 1.67 1.72 1.55 15 Alginic Acid 1.62 1.80 1.52 16 Talc 1.73 1.68 1.60 17 Colloidal silicon dioxide
1.59 1.70 1.67 18 Magnesium stearate 1.58 1.53 1.88 19 Sodium Stearyl Fumarate 1.64 1.83 1.82 20 Hydrogenated Vegetable Oil
1.71 1.65 1.56 21 Stearic Acid 1.73 1.69 1.61 22 Sodium starch glycolate 1.62 1.60 1.59 23 Croscarmellose sodium
1.82 1.78 1.49 24 Polyplasdone 1.81 1.93 1.94 25 L-HPC 1.71 1.62 1.55 26 Opadry 1.49 1.38 1.35 27 API+ HPMC capsule shell 1.78 1.70 1.48 28 API+ Gelatin capsule shell 1.56 1.40 1.54 29 Ethyl cellulose 1.79 1.68 1.61 3
0 Silicified microcrystalline c
ellulose 1.83 1.64 1.67 31 Maltose 1.70 1.59 1.54 32 Polyethylene Glycol 1.87 1.74 1.66 33 PEO 1NF 1.67 1.71 1.67 34 Methacrylic acid copolymer 1.86 1.69 2.84 [0490] The change in total impurities over time are as shown in Tables 6-38 below. [0491] 7RWDO^,PSV^ ^7RWDO^,PSXULWLHV^^^^^^^^^Z^Z^^,JQRUHG^LPSXULWLHV^^^^^^^^
O W
1 0 0 / 1 5 8 1 1 0 -
4 . 4 3 5 3 3 5 5 1 4 3 4 4 . 2 2 2 1-
4 . 5 2 2 2 - U
1 1 . 0 . 0 . 0 U
3 1 . 1 . 0 . 0 . 0 I B T S 4 1 3 6 5 s e 4 3 6 5 : - . . U
2 4 . 1 c n 1 - . 2 4 . 1 o 1 a t U s
1 N t e 3 2 0 6 b u 3 2 k 1-
2 . 4 0 5 0 c U
2 . 1 . 0 . 0 S 1-
2 . 0 4 6 0 5 0 U
2 . 1 . 0 . 0 o 1 d 1 D s e t y e a e c l n 2 1 8 l - 3 . 2 4 o a . e 2 8 R 1-
3 . 2 4 . o t s U
2 1 1 a U
2 1 1 C b e u r S 1 d 1 1 5 e - . 2 3 7 A 1 1 1 5 2 7 6 t
1 . 0 a U
1 1 . 0 % - . U
1 3 1 . 0 0 1 . 0 . 0 l e t e R
0 7 a r d 7 a 1 e -
1 . 8 2 4 3 7 . 1 . 1 . 0 . y 0 1-
1 . 8 2 2 4 4 . 1 . 0 . 0 . r U
1 1 1 1 1 1 h o U
1 1 1 1 1 1 A
n o %
I 9-
4 7 2 1 l M 9-
4 7 2 l P U
. 9 . 1 a t S 6 6 2 5 . 6 . 5 . e s U
. 1 9 . 1 a t S 0 7 2 1 . 6 6 A
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1 1 1 o t o R
. . c T 1 1 1 e t a r 8 a
- 1 U
3 5 a .
9 8 . 0 3 L 8-
1 2 2 3 5 9 5 0 m -
7 . 2 U
. . . 3 2 7 2 6 9 . u U
1 1 +I 8 0 0 2 - . P U
6 9 1 . 1 F e 7 n -
5 1 3 2 A
5 3 2 i U
. 9 8 . 0 6 0 . 0 2 2 2 e 7 - 1 9 0 2 2 2 m -
9 . 3 8 n U
. . . 2 9 3 1 a U
5 . 1 i 8 0 0 - . 8 U
5 . 1 -
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n 6-
6 a U
5 7 . 8 5 0 4 0 4 a 0 0 -
2 7 . 0 . 0 . 0 . 0 1 2 4 . 7 7 -
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5 7 . 8 5 0 4 0 4 0 7 . 0 . 0 . 0 . 0 1 2 0 4 . 7 7 p - 5 . o U
1 1 a p - 5 . o U
1 1 r p l y 5-
8 6 5 6 r 6 p h
t U
4 . 8 l 5 8 6 6 6 6 7 . 0 0 . 0 0 . 0 0 2-
0 . 3 y - U
4 . 8 7 . 0 . 0 . 0 2 0 . 3 e U
5 7 1 . 0 0 0 1 h t - U
5 7 1 . 1 m
e i d-
4-
5 U
0 1 . 8 m i 4-
5 1 7
. 0 9 1 5 6 . 8 6 6 0 5 0 3 0 d- U
0 . 8 7 . 9 1 5 6 8 6 7 6 5 N , - U
4 . 1 . 0 . 0 . 0 N , 0 - . U
4 . 0 1 . 0 0 . 0 0 . 0 N
1 N
1 -)
l y 3 -
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6 0 1 1 -) -
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1 0 3 . 7 6 . 0 0 . 8 1 0 1-
3 . 4 6 3 0 -l U
4 1 . 1 . 0 1- U
4 1 . 1 . 0 o
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1 - U
6 3 o . 5 4 . 7 0 0 1 4 5 6 5 3 d n 2-
1 6 3 . 5 . 7 0 5 0 6 3 H
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1 1 . 0 . 0 . 0 i- U
4 0 1 H -
4 . U
4 6 1 . 1 1 . 0 0 . 0 0 . 0 - 1 y 4 -
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4 3 8 3 6 4 h U
. t 3 . 0 1-
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4 6 3 1
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- r m l a l e 0 5 0 a v 5 0 - 5 v r 0 5 0 a 1
t T 1 T
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n / H
( . n o / H
n / H e
i l d C ° R o it
i C R 7 i
t i C R oi
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d ° e d ° i %
d C ° a
o 4 5 n 0 %
5 l n 0 4 5 n 0 %
5 C
7 o 4 7 b a o 7 o 4 7 T C T C
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O W
1 0 0 / 1 5
8 1 1 0 -
4 . 4 3 5 3 3 6 5
1 4 3 4 0 . 2 2 2 1-
4 . 5 2 2 3 - U
1 1 . 0 . 0 . 0 U
3 1 . 1 . 0 . 0 . 0 I B T 4
S 1 3 6 5 4
3 6 5 : - . 4 . U
2 o 1 . 1 1
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2 1 . 1 N t e s 3
2 k e c 1-
2 . 0 7 5 3
2 2 0 7 5 2 4 . 0 1 . 0 0 . 1 0
- . 2 4 . 0 . 0 . c n a U
1 U
1 1 0 0 o D t s s y b e e u 2
8 3 2 c n 2
8 2 l o S 1 - . d U
2 4 1 . 1 a t 1 s -
3 . U
2 4 1 . 1 o C e t b a
l u e 1
1 1 5 S . 2 3 7 0 d 1
1 1 5 . 2 7 R
- a U
1 . 1 . 0 e t - 1 3 . 0 1 . 0 e
1 a U
1 r l e A 0
1 7 1 . 8 2 4 1 2 R 1 7 0 a 0
1 7 1 . 8 2 4 1 1 7 % -
1 . 1 . 1 . 1 . e -
1 . . 1 . 1 . h U
1 1 r A U
1 1 1 1 1 c
r a t S
9-
4 7 2 % . 1 . l n 9-
4 7 2 . 1 l e U
9 1 a z
t i
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7 5 3 . 6 . 6 . i li U
9 . 1 a t S 6 6 1 1 . 6 . 9 . a
T 1 1 1 s o u T R
1 1 1 M
8 + -
1 e U
3 5 . 9 8 . 0 3
2 N 8 7 2 + -
1 U
3 5 . 9 3 0 8 . 0 . 3
2 7 2 I 2 - . 9 0 2 - . 9 P U
6 1 . 1 I P U
6 1 . 1 A e
7 n -
5 1 3 3 A i U
. 9 8 . 0 0 . 0 2
2 2 9 . 3 e 7 n -
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1 3 3 . 9 8 . 0 0 . 7 0 2
2 2 9 3 2 1 m
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5 - 1 . 1 i m
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6 a U
5 7 . 8 5 0 5 0 4 a 0 - 7
. 0 . 0 . 0 . 0 1
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2 0 4 . 7 7 4 0 o U
1 1 a p - U
5 1 . 1 . 0 r o p l 5 y -
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4 . 8 l 5 8 6 6 7 . 0 0 . 0 0 . 0 0
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. 8 7 . 0 0
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5 1 . 1 h t -
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5 1 . 1 m
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5 N U
0 1 . 8 5 m i 4-
5 0 1 8 5 , 7 . 0 9
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6 . 8 6 6 0 7 0 5 0 d- U
. 7 . 0 9
1 6 . 8 6 6 0 0 1 7 1 U
4 1 . 1 . 0 . 0 . 0 N , - U
4 . 1 . 0 . 0 . 0 N N
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1 . 7 4 6
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0 1 0 7 . 4 6 3 y 8
1 U
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. 0 . - 6 0 - . 6 . 0 . l U
4 1 0 1 4 1 0 o
1 -l U o
1 d ni 2-
1 - U
6 3 . 5 4 . 7 0
1 0 4 5 0 6 3 d ni 2-
1 6 3 . 5 . 7
0 4 5 1 5 3 H
- . 4 6 . 1 0 0 U
4 0 1 . 6 1 0 0 1 U
1 1 . 0 . 0 . 0 - H - U
4 1 . 1 . 0 . 0 . 0 - 1 y x 1 o -
4 3 8 -
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4 1 3 y x 1-
4 3 8 3 6
4 1 h U
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4 6 1 . 0 U
. . 1 0 t . 6 3 0 1 . 0 o h 3 0 - e U
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n o / H
( . n o / H
n / H e
i l d C ° R it
i C R 9 i
t i R o it
R b
n 0 %
d ° e d C ° i %
d C ° a
o 4 5 n 0 %
5 l n 0 4 5 n 0 %
5 C
7 o 4 7 b a o 7 o 4 7 T C T C
C
O W
1 0 5 0 / 1 1 - 4 . 4 5 5 2 7 2 1 3 1 5 1 8 1 4 3 9 U
3 1 . 1 . 0 . 0 . 0 0 -
4 . 3 5 . 2 5 2 2 - U
1 1 . 0 . 0 . 0 I 4 3
5 B T 4 3 5 s e 1-
6 . c U
2 4 1 . 1 S 1 : - 6 . . U
2 4 . n o 1 1 a t s b 3 1 2
2 0 4 7 5 N t e 3 2 0 u - . U
2 . 0 1 . 0 0 . 0 k 1-
2 . c U
2 4 6 . 0 5 S 1 1 . 0 . d o 1 0 0 e t D s a l 2 1 8 -
3 . 2 4 y e c 2 1 8 3 . 2 e R U
2 1 . 1 e l n - o a o t 2 4 . 1 a s U
1 e r 1 1
C b u A 1-
5 . 2 3 7 6 . 0 . 0 . S 1 1 1 5 . 2 3 7 0 7 0 U
1 1 1 0 0 d -
1 . 1 . . 0 % e
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1 0 e a
t l
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1 . 8 2 4 6 4 . 1 . 0 . 1 R
0 7 1 8 2 6 9 p s U
1 1 1 1 1 . 1 a 1 - . 1 2 . 1 0 0 1 . 1 . 1 . 1 o e r U
1 h P
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4 2 U
7 . 1 9 . % 9-
4 C U
7 2 . 1 9 . l u 1 a t S 4 i 1 l 7 9 6 8 6 c l a t S
7 6 5 6 1 7 C o T R
. 1 . 1 . 1 a c o R
. 1 . 1 . 1 M
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1 5 T +
8 1 D U
3 . 9 8 . 0 I
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. 8 . 0 3 2-
7 . 2 + 2 7 2 6 9 . I P - . 6 9 . A U
1 1 A
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5 1 1 3 3 U .
9 . 0 . 1 e n i 7-
5 1 3 9 2 0 e U
8 0 0 2
8 2 m U
. 8 . 0 . 0 2 2 2 a - 9 . 3 8 n i 2 2-
9 . 3 8 . 1 - U
5 1 . 1 m a 6 U
5 1 2 - 6- -
5 7 5 4 4 . 8 0 0 0 1 n 6 6 7 5 4 4 2- U
7 . 0 . 0 . 0 . 0 a -
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5 . 8 o
7 . 0 0 . 0 0 . 0 0 . 0 1 2 0 - 4 . 7 7 n a 1 2 0 -
4 . 7 7 r U
5 p 1 . 1 p o r 5-
8 6 4 U
5 . 1 l p y l U
4 . 8 7 . 0 1 0 . 0 h 5 t -
8 e U
4 6 8 9 . 8 0 0 7 . 0 . 0 . 0 0 6 2-
0 . 3 5 7 y . h t 0 2 6
0 . 3 7 m
e - . U
1 1 i m 4-
5 0 1 U
5 1 .
8 . 1 d-
4 5 1 i d U
7 0 N -
, U
0 . 8 7 . 0 9 1 5 - 6 . 8 4 6 8 . 0 6 - 9 5 .
0 6 . 0 . N , 1-
6 . 8 4 6 6 . 0 6 0 5 0 1 . 0 . 0 . N- U
1 1 0 0 0 N
3-
0 1 0 7 U
1 0 )l -) l U
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0 1 0 4 -
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6 0 0 1-
3 . 4 6 3 0 y 0 - 8 1 1
3 4 4 3 o U
4 1 . 1 . 0 1 -l - . 6 . 0 . 0 d o 2-
1 6 3 U
4 1 0 . 0 n
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2-
1 6 3 d 5 7 0 5 1 6 3 ni U
4 0 7 0
5 6 5 3 H U
. 1 4 . 0 1-
4 . - U
4 6 1 . 1 1 . 0 0 . 0 0 . -
0 H
1 1 -
4 . - 1-
4 8 U
4 6 1 . 0 0 0 1 . 0 . 0 . 0 y
x o 1 y U
3 . 3 3 . 0 h - 4 3 8 6 4 x 6 4 t U
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0 . 1 U
4 6 3 1
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4 6 3 . 0 1 . 0 m-
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3 T
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3 T
v r e t 0 5 0 ( T
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3 -
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n I v r e t 0 5 0 T 1 T
3 T
R I n ( I ) R
n . n
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t / H
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R o i H t
1 1 t i 5 7 n / H oi
t / H e
d C ° i d C ° R e
d n
C R i d C ° R l b n a o 0 4 %
5 n 0 %
5 l o ° n 0 %
5 C
7 o 4 7 b a 0 4 o 4 7 T C T C
C
O W
1 0 5 0 / 1 1 - 4 . 4 5 5 7 8 5 1 .
2 2 2 . 1-
4 . 4 5 4 7 9 . 2 2 2 . 1 U
3 1 1 . 0 . 0 0 U
3 1 1 . 0 . 0 0 8 0-
I 4 1 3
6 5 s e 4 1 3
6 5 B - . 4 T U
2 . 1 c n - . 4 U
2 . 1 S 1 a : t 1 . o 3 2
s 0 7 5 b 3 2
0 7 N 1-
2 . 4 0 0 u t e U
2 1 . 1 . 0 . 0 S 1-
2 . 4 0 5 0 d e U
2 1 . 1 . 0 . 0 k c s t o e c D n 2 1 8 -
3 . 2 a l 4 4 2 8
2 . 0 . e 1-
3 . 4 . y a U
2 1 0 R 2 1 e t l s 1 a U
o b e 1 o u r C S 1 d 1 1
5 2 7 A 1 1
5 2 7 e - . t U
1 3 . 0 . %
1 - . 1 3 . 0 . a 1 1 0 U
1 1 0 l b e
a R
0 a 1 7 t 7 e -
1 . 8 2 4 5 2 Y 0 .
1 . 1 . 1 . S 1-
1 . 8 2 2 0 8 . 1 . 2 . 0 . r U
1 1 1 1 1 1 A U
1 1 1 1 1 1 A
E % l 9-
4 7 2 ® o
. 1 V 9-
4 7 2 1 t U i
9 . 1 l L U
. . a O 9 1 l n n t S
1 7 5 7 2 7 S a t S
6 6 6 7 3 6 a 8 M-
1 U
3 5 o R
. 1 . 1 . 1 O o R
. 1 . 1 . 1 .
9 8 . T 0 R 8 P -
1 U
3 5 . 9 T 8 . + 2
0 I
3 2 + 3 2
2 P
2-
7 . 6 9 . 2 1
I P - 7 . 6 9 . A
7-
5 e U
1 3 . 9 3 0 U
1 7-
5 3 2 U
1 1 n
8 . 0 . 0 A U
1 . 9 0 8 . 0 . i
2 2
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2-
9 . 3 n 0 i 2 2
9 9
3 2 a
- 5 8 . m 2 - . 5 8 . 1 2 6-
6 U
1 U
1 - U
5 7 7 5 5 . 8 . 0 . 0 . 0 . 1 a - 6-
6 5 7 5 5 4 . 8 . 0 0 0 1 n 7 0 0 0 0 2 U
7 0 . 0 . 0 . 0 a
1 p 2 0
4 o - . 7 - 7
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4 . 7 7 r 5-
8 4 6 8 4 0 U
5 1 . 1 p o -
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Cooley Docket No.: STBI-081/001WO EQUIVALENTS [0492] The details of one or more embodiments of the disclosure are set forth in the accompanying description above. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present disclosure, the preferred methods and materials are now described. Other features, objects, and advantages of the disclosure will be apparent from the description and from the claims. In the specification and the appended claims, the singular forms include plural referents unless the context clearly dictates otherwise. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. All patents and publications cited in this specification are incorporated by reference. [0493] The foregoing description has been presented only for the purposes of illustration and is not intended to limit the disclosure to the precise form disclosed, but by the claims appended hereto.