IUCrData
September 7, 2023
Duyen N. K. Pham, Nathan Sackett, Andrew R Chadeayne et al.
1 citation
The solid-state structure of the title salt/adduct (systemic name: bis{[2-(4-acetyloxy-1 H -indol-3-yl)ethyl](ethyl)propylazanium} but-2-enedioate–( E )-butenedioic acid (1/1)), 2C 17 H 25 N 2 O 2 + ·C 4 H 2 O 4 2− ·C 4 H 4 O 4 , was determined by single-crystal X-ray diffraction. The asymmetric unit consists of a singly protonated tryptammonium cation, one half of a fumarate dianion and one...
ACS Pharmacology & Translational Science
March 10, 2023
Marilyn Naeem, Grant C. Glatfelter, Duyen N. K. Pham et al.
25 citations
Analogues of 4-phosphoryloxy-N,N-dimethyltryptamine (psilocybin) are being sold on recreational drug markets and developed as potential medications for psychedelic-assisted therapies. Many of these tryptamine-based psilocybin analogues produce psychedelic-like effects in rodents and humans primarily by agonist activity at serotonin 2A receptors (5-HT2A). However, the comprehensive...
ACS Pharmacology & Translational Science
November 2, 2022
Eline Pottie, Marilyn Naeem, Vamshikrishna Reddy Sammeta et al.
91 citations
4-Phosphoryloxy-N,N-dimethyltryptamine (psilocybin) is a naturally occurring tertiary amine found in many mushroom species. Psilocybin is a prodrug for 4-hydroxy-N,N-dimethyltryptamine (psilocin), which induces psychedelic effects via agonist activity at the serotonin (5-HT) 2A receptor (5-HT2A). Several other 4-position ring-substituted tryptamines are present in psilocybin-containing...
ACS Omega
July 5, 2022
Grant C. Glatfelter, Duyen N. K. Pham, Donna Walther et al.
14 citations
Aeruginascin (4-phosphoryloxy-N,N,N-trimethyltryptammonium) is an analogue of psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) that has been identified in several species of psilocybin-containing mushrooms. Our team previously reported the synthesis, structural characterization, and biological activity of the putative metabolite of aeruginascin (4-hydroxy-N,N,N-trimethyltryptammonium;...
ChemBioChem
May 18, 2022
Sebastian Dörner, Kai Rogge, Janis Fricke et al.
43 citations
Abstract Psilocybe magic mushrooms are best known for their main natural product, psilocybin, and its dephosphorylated congener, the psychedelic metabolite psilocin. Beyond tryptamines, the secondary metabolome of these fungi is poorly understood. The genomes of five species ( P. azurescens , P. cubensis , P. cyanescens , P. mexicana , and P. serbica ) were browsed to understand more profoundly...
Acta Crystallographica Section E Crystallographic Communications
April 13, 2021
Duyen N. K. Pham, Andrew R Chadeayne, James A. Golen et al.
3 citations
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}...
Acta Crystallographica Section E: Crystallographic Communications
March 19, 2021
Duyen N. K. Pham, Vamshikrishna Reddy Sammeta, Andrew R Chadeayne et al.
The synthesis and solid-state structure of the fumarate salt of the synthetic psychedelic 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT) is reported.
Acta Crystallographica Section E Crystallographic Communications
January 29, 2021
Duyen N. K. Pham, Andrew R Chadeayne, James A. Golen et al.
7 citations
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:...
Acta Crystallographica Section E Crystallographic Communications
January 8, 2021
Duyen N. K. Pham, Andrew R Chadeayne, James A. Golen et al.
9 citations
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...
ACS Omega
July 2, 2020
Andrew R Chadeayne, Duyen N. K. Pham, Brian G. Reid et al.
31 citations
The putative active metabolite of aeruginascin, a naturally occurring tryptamine of "magic mushrooms," has been synthesized and structurally characterized. Competitive radioligand binding assays demonstrate that it has a high affinity at human serotonin receptors 5-HT1A, 5-HT2A, and 5-HT2B, though it does not bind at the 5-HT3 receptor, where activity was previously predicted.
IUCrData
April 1, 2020
Andrew R Chadeayne, Duyen N. K. Pham, James A. Golen et al.
7 citations
The solid-state structure of the synthetic psychedelic 5-methoxy-N,N-diallyltryptamine (5-MeO-DMT) is reported in its freebase form.
Acta Crystallographica Section E Crystallographic Communications
March 27, 2020
Andrew R Chadeayne, Duyen N. K. Pham, James A. Golen et al.
13 citations
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...
Acta Crystallographica Section E Crystallographic Communications
March 10, 2020
Andrew R Chadeayne, Duyen N. K. Pham, James A. Golen et al.
12 citations
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...
Acta Crystallographica Section E Crystallographic Communications
August 15, 2019
Andrew R Chadeayne, Duyen N. K. Pham, James A. Golen et al.
10 citations
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...