Acta crystallographica. Section E, Crystallographic communications
September 1, 2026
Marilyn Naeem, Andrew R Chadeayne, James A Golen et al.
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...
ACS Chemical Neuroscience
May 27, 2026
Grant C. Glatfelter, Serena S. Schalk, Donna Walther et al.
High Resolution Image Download MS PowerPoint Slide Tryptamine psychedelics induce psychoactive effects via agonist actions at serotonin 2A receptors (5-HT 2A ), but the compounds are generally nonselective. 4-Methoxy- N -methyl- N -isopropyltryptamine (4-MeO-MiPT) is a 5-HT 2A agonist which also blocks the 5-HT transporter (SERT) and has blunted visual and other psychedelic effects in humans....
IUCrData
June 1, 2025
Maria Naeem, Andrew R Chadeayne, James A. Golen et al.
The solid-state structure of the hydrofumarate salt of the synthetic psychedelic 4-hydroxy-N,N-diisopropyltryptamine (4-HO-DiPT) is reported.
Journal of Analytical Toxicology
May 26, 2025
Malik Schoffner, Vamshikrishna Reddy Sammeta, Marilyn Naeem et al.
2 citations
Abstract 4-Phosporyloxy-N, N-dimethyltryptamine (psilocybin) is a psychedelic tryptamine found in certain mushroom species that has shown efficacy in the treatment of various psychiatric disorders. In conjunction with the renewed interest in therapeutic effects of psychedelics, there has been an increase in psilocybin-like designer tryptamines appearing in non-medical drug markets. The present...
ACS Chemical Neuroscience
December 18, 2024
Grant C. Glatfelter, Allison A Clark, Natalie G. Cavalco et al.
14 citations
5-methoxy-N,N-dimethyltrytpamine (5-MeO-DMT) analogs are used as recreational drugs, but they are also being developed as potential medicines, warranting further investigation into their pharmacology. Here, we investigated the neuropharmacology of 5-MeO-DMT and several of its N-alkyl, N-allyl, and 2-methyl analogs, with three major aims: 1) to determine in vitro receptor profiles for the...
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...
Acta Crystallographica Section E Crystallographic Communications
March 10, 2023
U. Laban, Marilyn Naeem, Andrew R Chadeayne et al.
2 citations
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 )...
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...
Acta Crystallographica Section E: Crystallographic Communications
September 22, 2022
Maria Naeem, Barbara E. Bauer, Andrew R Chadeayne et al.
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...
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
May 6, 2022
Marilyn Naeem, Alexander M. Sherwood, Andrew R Chadeayne et al.
5 citations
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 FASEB Journal
May 1, 2022
Grant C. Glatfelter, David R. Manke, Andrew R. Chadayne et al.
1 citation
4‐phosphorloxy‐ N,N ‐dimethyltryptamine (psilocybin) is a naturally occurring psychedelic compound that is being investigated in clinical studies in conjunction with psychotherapy for treatment of several psychiatric disorders. It is well established that 4‐hydroxy‐ N,N ‐dimethyltryptamine (psilocin) is the bioactive metabolite of psilocybin which mediates its in vivo psychedelic activity in...
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...
IUCrData
November 27, 2020
Vamshikrishna Reddy Sammeta, Sivappa Rasapalli, Andrew R Chadeayne et al.
4 citations
The title compound, 4-hydroxy- N , N -di- n -propyltryptammonium (4-HO-DPT) chloride {systematic name: N -[2-(4-hydroxy-1 H -indol-3-yl)ethyl]- N -propylpropan-1-aminium chloride}, C 16 H 25 N 2 O + ·Cl − , has a singly protonated tryptammonium cation and one chloride anion in the asymmetric unit. A series of N—H...Cl and O—H...Cl hydrogen bonds connect the ions together in ladder chains along...
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...
Acta Crystallographica Section E Crystallographic Communications
May 31, 2019
Andrew R Chadeayne, James A. Golen, David R. Manke
20 citations
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...