Bis(4-acetoxy-N,N-dimethyltryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
Andrew R Chadeayne, James A. Golen, David R. Manke
Acta Crystallographica. Section E, Crystallographic Communications May 31, 2019 DOI: 10.1107/s2056989019007370 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Crystallographic study Peer reviewed |
|---|---|
| Topics | Psilocybin |
| Keywords | Protonation Hydrogen bond Indole test Ammonium Stereochemistry Crystallography |
| Citations | 20 |
| Key points | Psilacetin fumarate forms infinite one-dimensional chains via N—H...O hydrogen bonds between the ammonium and indole hydrogen atoms and fumarate oxygen atoms. |
Abstract
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 and the fumarate O atoms. The hydrogen bonds hold the ions together in infinite one-dimensional chains along [111].
Citations in the library
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- Norpsilocin: freebase and fumarate salt Acta Crystallographica. Section E, Crystallographic Communications March 27, 2020
- Bis(4-hydroxy-N-isopropyl-N-methyltryptammonium) fumarate: a new crystalline form of miprocin Acta Crystallographica. Section E, Crystallographic Communications March 10, 2020
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