Bis(4-acetoxy-N,N-dimethyltryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug

The crystal structure of psilacetin fumarate, a salt of the psychedelic drug psilacetin, was determined. The asymmetric unit contains one protonated psilacetin cation and half of a fumarate dianion. Hydrogen bonds between the ammonium and indole groups of psilacetin and the fumarate oxygen atoms link the ions into infinite one-dimensional chains along the [111] direction.

Study at a glance

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].