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

Abstract

The title compound (systematic name: bis{2-[4-(acetyloxy)-1H-indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C14 H19N2 O2+ ·C4H2O4 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].