Bis(4-acet-oxy- N , N -di-methyl-tryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug

The title compound (systematic name: bis-{2-[4-(acet-yloxy)-1 -indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C H N O ·C H O , 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 fuma...

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Bibliographic Details
Published in:Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2019-06, Vol.75 (Pt 6), p.900-902
Main Authors: Chadeayne, Andrew R, Golen, James A, Manke, David R
Format: Article
Language:English
Subjects:
crystal structure
hydrogen bonding
Research Communications
tryptamines
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Summary:The title compound (systematic name: bis-{2-[4-(acet-yloxy)-1 -indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C H N O ·C H O , 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].
ISSN:2056-9890
2056-9890
DOI:10.1107/S2056989019007370