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....
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...
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
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...