The solid-state structures of N-ethyl-4-hy-droxy-tryptamine (4-HO-NET) {systematic name: 3-[2-(ethyl-amino)-eth-yl]-1H-indol-4-ol}, C12H16N2O, and 4-hy-droxy-N-propyl-tryptamine (4-HO-NPT) {systematic name: 3-[2-(propyl-amino)-eth-yl]-1H-indol-4-ol}, C13H18N2O, are reported. Both compounds possess a single tryptamine mol-ecule in the asymmetric unit that exhibits an inter-nal O-H⋯N hydrogen...
Diphenidine (1a), a dissociative anaesthetic, was first reported in 2013. Since then, a number of derivatives e.g. 2-methoxphenidine (1b) have been produced by clandestine laboratories and sold as research chemicals. Fluorinated diphenidines, namely, [1-(2,6-di-fluoro-phen-yl)-2-phenyl-eth-yl]di-methyl-aza-nium chloride, C16H18F2N+·Cl-, (I),...
The title compound, C12H16N2O, is a hy-droxy-substituted mono-amine alkaloid, and the primary metabolite of the naturally occurring psychedelic compound psilocybin. Crystalline forms of psilocin are known, but their characterization by single-crystal structure analysis is limited. Herein, two anhydrous polymorphic forms (I and II) of psilocin are described. The crystal structure of polymorphic...
The title compound, 4-hydroxy- N -isopropyltryptamine ( 4 ) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]ethyl}-1 H -indol-4-ol), C 13 H 18 N 2 O, was synthesized in three steps from 4-benzyloxyindole ( 1 ) (systematic name: 4-phenoxy-1 H -indole), C 15 H 13 NO. ( 1 ) was treated with oxalyl chloride and isopropylamine to produce N -isopropyl-4-benzyloxy-3-indoleglyoxylamide ( 2 )...
The solid-state structures of two solvated forms of 4-glutarato- N , N -diisopropyltryptamine were determined by single-crystal X-ray diffraction, namely, 5-[(3-{2-[bis(propan-2-yl)azaniumyl]ethyl}-1 H -indol-4-yl)oxy]-5-oxopentanoate methanol monosolvate, C 21 H 30 N 2 O 4 ·CH 3 OH, and the analogous ethanol monosolvate, C 21 H 30 N 2 O 4 ·C 2 H 6 O. In both compounds, the 4-glutarato- N , N...
The title compound, baeocystin or 4-phosphoryloxy- N -methyltryptamine {systematic name: 3-[2-(methylazaniumyl)ethyl]-1 H -indol-4-yl hydrogen phosphate}, C 11 H 15 N 2 O 4 P, has a single zwitterionic molecule in the asymmetric unit. The molecule has an intramolecular N—H...O hydrogen bond between the ammonium cation and the hydrophosphate anion. In the crystal, the molecules are linked by...
The solid-state structures of the synthetic psychedelic 5-methoxy- N , N -di- n -propyltryptamine (5-MeO-DPT) {systematic name: N -[2-(5-methoxy-1 H -indol-3-yl)ethyl]- N -propylpropan-1-amine}, C 17 H 25 N 2 O, and its fumarate salt, bis(5-methoxy- N , N -di- n -propyltryptammonium) fumarate (systematic name: bis{ N -[2-(5-methoxy-1 H -indol-3-yl)ethyl]- N -propylpropan-1-aminium}...
The solid-state structure of the bufotenine derivative bis(5-methoxy-2, N , N -trimethyltryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis{[2-(5-methoxy-2-methyl-1 H -indol-3-yl)ethyl]dimethylazanium} (2 E )-but-2-enedioate), 2C 14 H 21 N 2 O + ·C 4 H 2 O 4 2− , the bufotenidine derivative 5-methoxy-2, N , N , N -tetramethyltryptammonium (5-MeO-2-Me-TMT) iodide {systematic name:...
The solid-state structures of the salts of three psilacetin derivatives, namely, 4-acetoxy- N -ethyl- N -methyltryptammonium (4-AcO-MET) hydrofumarate {systematic name: [2-(4-acetyloxy-1 H -indol-3-yl)ethyl](methyl)ethylazanium 3-carboxyprop-2-enoate}, C 15 H 21 N 2 O 2 + ·C 4 H 3 O 4 − , 4-acetoxy- N -allyl- N -methyltryptammonium (4-AcO-MALT) hydrofumarate {systematic name: [2-(4-acetyloxy-1...
The structures of the hydrofumarate salts of two N,N-dimethyltryptamine (DMT) derivatives, the synthetic psychedelics N-ethyl-N-propyltryptamine (EPT) and N-allyl-N-methyltryptamine (MALT), are reported.
The solid-state structures of the naturally occurring psychoactive tryptamine norpsilocin {4-hydroxy- N -methyltryptamine (4-HO-NMT); systematic name: 3-[2-(methylamino)ethyl]-1 H -indol-4-ol}, C 11 H 14 N 2 O, and its fumarate salt (4-hydroxy- N -methyltryptammonium fumarate; systematic name: bis{[2-(4-hydroxy-1 H -indol-3-yl)ethyl]methylazanium} but-2-enedioate), C 11 H 15 N 2 O + ·0.5C 4 H 2...
The title compound, bis(4-hydroxy- N -isopropyl- N -methyltryptammonium) (4-HO-MiPT) fumarate (systematic name: bis{[2-(4-hydroxy-1 H -indol-3-yl)ethyl](methyl)propan-2-ylazanium} but-2-enedioate), 2C 14 H 21 N 2 O + ·C 4 H 2 O 4 2− , has a singly protonated tryptammonium cation and one half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in...
The solid-state structures of the salts of two substituted tryptamines, namely N -isopropyl- N -methyltryptaminium (MiPT) fumarate {systematic name: [2-(1 H -indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate}, C 14 H 21 N 2 + ·C 4 H 3 O 4 − , and 4-hydroxy- N -isopropyl- N -methyltryptaminium (4-HO-MiPT) fumarate monohydrate {systematic name: [2-(4-hydroxy-1 H...
The title compound (systematic name: bis{2-[4-(acetyloxy)-1 H -indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C 14 H 19 N 2 O 2 + ·C 4 H 2 O 4 2− , has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N—H...O hydrogen bonds between the ammonium H atoms and the fumarate O atoms, as well as N—H...O hydrogen bonds between the indole H atoms...