CAAMTECH, INC.

The disclosure relates to a compound of formula (I): The disclosure also relates to a compound of formula (Ia): The disclosure relates to compositions comprising, consisting essentially of, or consisting of a compound of formula (I) or formula (Ia) and an excipient. The disclosure also relates to pharmaceutical compositions comprising a therapeutically effective amount of a compound of formula (I) or formula (Ia) where the excipient is a pharmaceutically acceptable carrier. The disclosure further relates to therapeutic uses of compounds of formula (I) or formula (Ia).

The disclosure relates to [2-5-chloro-1H-indol-3-yl)ethyl](propan-2-yl)azanium iodide (5-chloro-N isopropyltryptammonium iodide or 5-Cl-NiPT iodide), crystalline 5-Cl-NiPT iodide, [2-(5-methoxy-1H-indol-3-yl)ethyl](propan-2-yl)azanium iodide (5-methoxy-N-isopropyltryptammonium iodide or 5-MeO-NiPT iodide), crystalline 5-MeO-NiPT iodide, [2-(5-methyl-1H-indol-3-yl)ethyl](propan-2-yl)azanium iodide (5-methyl-N-isopropyltryptammonium iodide or 5-Me-NiPT iodide), crystalline 5-Me-NiPT iodide, [2-(2-methyl-1H-indol-3-yl)ethyl](propan-2-yl)azanium iodide (2-methyl-N-isopropyltryptammonium iodide or 2-Me-NiPT iodide), crystalline 2-Me-NiPT iodide, [2-(7-methyl 1H-indol-3-yl)ethyl](propan-2-yl)azanium iodide (7-methyl-N-isopropyl-tryptammonium iodide or 7-Me-NiPT iodide), crystalline 7-Me-NiPT iodide, [2-(5-fluoro-1H-indol-3-yl)ethyl](propan-2-yl)azanium iodide (5-fluoro-N-isopropyltryptammonium iodide or 5-F-NiPT iodide), crystalline 5-F-NiPT iodide, and specific crystalline forms thereof, including crystalline form 1 of 5-Cl-NiPT iodide, crystalline form 1 of 5-MeO-NiPT iodide, crystalline form 1 of 5-Me-NiPT iodide, crystalline form 1 of 2-Me-NiPT iodide, crystalline form 1 of 7-Me-NiPT iodide, and crystalline form 1 of 5-F-NiPT iodide, to compositions containing the same, and to methods of treatment using them. This disclosure relates to monoalkylated and dialkyled tryptamine analogs, and to methods of treatment/therapeutic uses thereof. This disclosure relates to an improved method of making monoalkylated and dialkylated tryptamine analogs.

The disclosure relates to compounds of formulae (I), (II), (III), and (IV): The disclosure relates to compositions comprising, consisting essentially of, or consisting of a compound of formulae (I), (II), (III), or (IV) and an excipient. The disclosure also relates to pharmaceutical compositions comprising a therapeutically effective amount of a compound of formulae (I), (II), (III), or (IV) where the excipient is a pharmaceutically acceptable carrier. The disclosure further relates to therapeutic uses of compounds of formulae (I), (II), (III), or (IV).

This disclosure relates to [2-(5-hydroxy-1H-indol-3-yl)ethyl]tripropylazanium iodide monohydrate (5-hydroxy-N,N,N-tri-n-propyltryptammonium iodide monohydrate or 5-HO-TPT iodide monohydrate), crystalline 5-HO-TPT iodide monohydrate, (2-{4-[(4-chlorobenzenesulfonyl)oxy]-1H-indol-3-yl}ethyl)dipropylazanium chloride (4-[(4-chlorophenyl)sulfonyloxy]-N,N-di-n-propyltryptammonium chloride or 4-[(4-chlorophenyl)sulfonyloxy]-DPT chloride), crystalline 4-[(4-chlorophenyl)sulfonyloxy]-DPT, [2-(5-methoxy-1H-indol-3-yl)ethyl](methyl)(prop-2-en-1-yl)azanium (2E)-3-carboxyprop-2-enoate (5-methoxy-N-methyl-N-allyltryptammonium hydrofumarate or 5-MeO-MALT hydrofumarate), crystalline 5-MeO-MALT hydrofumarate, triethyl [2-(1 H-indol-3-yl)ethyl]azanium iodide (N,N,N-triethyltryptammonium iodide or TET iodide), crystalline TET iodide, {2-[4-(acetyloxy)-1H-indol-3-yl]ethyl}dimethyl(prop-2-en-1-yl)azanium iodide (4-acetoxy-N,N-dimethyl-N-allyltryptammonium iodide or 4-AcO-DMALT iodide), crystalline 4-AcO-DMALT iodide, and specific crystalline forms thereof, including crystalline form 1 of 5-HO-TPT iodide monohydrate, crystalline form 1 of -[(4-chlorophenyl)sulfonyloxy]-DPT chloride, crystalline form 1 of 5-MeO-MALT hydrofumarate, crystalline form 1 of TET iodide, and crystalline form 1 of 4-AcO-DMALT iodide, to compositions containing the same, and to methods of treatment using them.

The disclosure relates to crystalline form 1 of [2-(5-methoxy-1H-indol-3-yl)ethyl]dipropylamine (5-MeO-DPT) and to crystalline form 1 of bis([2-(5-methoxy-1H-indol-3-yl)ethyl]dipropylazanium) (2E)-but-2-enedioate (5-MeO-DPT fumarate), and to pharmaceutical compositions containing the compounds and methods of treatment using them.

Crystalline forms of 4-acetoxy-N,N-dimethyltryptamine (psilacetin), compositions containing that crystalline form, and their methods of use are disclosed. The crystalline forms of 4-acetoxy-N,N-dimethyltryptamine (psilacetin) according to the disclosure include crystalline 4-acetoxy-N,N-dimethyltryptammonium hydrofumarate, the fumarate salt of psilacetin, and/or crystalline bis(4-acetoxy-N,N-dimethyltryptammonium) fumarate, and pharmaceutical compositions containing a crystalline form of psilacetin.

The disclosure relates to crystalline form 1 of 5-hydroxy-N,N,N-trimethyl-tryptammonium (5-HTQ) iodide, and to pharmaceutical compositions containing the compound and to methods of treatment using it.

The disclosure relates to crystalline psilacetin derivatives, compositions containing those crystalline derivatives, and methods of treatment using them. The crystalline psilacetin derivatives include crystalline 4-acetoxy-N-methyl-N-ethyltryptammonium (4-AcO-MET) hydrofumarate (“crystalline 4-AcO-MET hydrofumarate”), crystalline 4-acetoxy-N-methyl-N-allyltryptammonium (4-AcO-MALT) hydrofumarate (“crystalline 4-AcO-MALT hydrofumarate”), and crystalline 4-acetoxy-N,N-diallyltryptammonium (4-AcO-DALT) fumarate fumaric acid (“crystalline 4-AcO-DALT fumarate fumaric acid”).

The disclosure relates to (2-{4-[(methoxycarbonyl)oxy]-1H-indol-3-yl}ethyl)bis(propan-2-yl)azanium chloride (4-methylcarbonato-N,N-diisopropyltryptramine chloride or 4-methylcarbonato-DiPT chloride), crystalline 4-methylcarbonato-DiPT chloride, [2-(1H-indol-3-yl)ethyl](propan-2-yl)amine (N-isopropyltryptamine or NiPT), crystalline NiPT, N-[2-(1H-indol-3-yl)ethyl]propan-2-amine hydrobromide (N-isopropyltryptamine hydrobromide or NiPT hydrobromide), crystalline NiPT hydrobromide, N-[2-(1H-indol-3-yl)ethyl]cyclohexanamine (N-cyclohexyltryptamine), crystalline N-cyclohexyltryptamine, 2-(1H-in-dol-3-yl)ethanamine (tryptamine), crystalline tryptamine, N-[2-(1H-indol-3-yl)ethyl]cyclohexanamine hydrobromide (N-cyclohexyltryptamine hydrobromide), crystalline N-cyclohexyltryptamine hydrobromide, and specific crystalline forms thereof, including crystalline form 1 of 4-methylcarbonrato-DiPT chloride, crystalline form 1 of NiPT, crystalline form 1 of NiPT hydrobromide, crystalline form 1 of N-cyclohexyltryptamine, crystalline form 1 of tryptamine, and crystalline form 1 of N-cyclohexyltryptamine hydrobromide, to compositions containing the same, and to methods of treatment using them.

The disclosure relates to {2-[4-(acetyloxy)-1H-indol-3-yl]ethyl}dimethyl(propan-2-yl)azanium iodide (4-acetoxy-/V,/V-dimethyl-/\/-isopropyltryptammonium iodide or 4-AcO-DMiPT iodide), crystalline 4-AcO DMiPT iodide, [2-(4-hydroxy-1H-indol-3-yl)ethyl]dimethyl(propan-2-yl)azanium iodide (4-hydroxy-A/,A/-dimethyl-A/-isopropyltryptam-monium iodide or 4-HO-DMiPT iodide), crystalline 4-HO-DMiPT iodide. ethyl[2-(4-hydroxy-1H-indol-3-yl)ethyl]dimethylazanium iodide (4-hydroxy-/V,/V-dimethyl-/\/-ethyltryptammonium iodide or 4-HO-DMET iodide), crystalline 4-HO-DMET iodide, and specific crystalline forms thereof, including crystalline form 1 of 4-AcO-DMiPT iodide, crystalline form 1 of 4-HO-DMiPT iodide, and crystalline form 1 of 4-HO-DMET iodide, to compositions containing the same, and to methods of treatment using them.