Bis(4-acetoxy-N,N-dimethyltryptammonium) fumarate: a new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug
Acta Crystallographica Section E Crystallographic Communications – May 31, 2019
Source: OpenAlex
Summary
Unlocking the precise **stereochemistry** of **psychedelics** like psilacetin is vital for advanced **drug studies**. **Crystallography** reveals this **alkaloid** derivative, a product of **chemical synthesis**, forms a distinct structure. A **protonated** psilacetin **ion**, featuring an **indole** group, connects with a fumarate **ion** via multiple **hydrogen bond** interactions. Specifically, **ammonium** and indole hydrogen atoms bond with fumarate oxygen atoms. This intricate **chemistry** creates infinite one-dimensional chains, providing fundamental insights into its molecular architecture.
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].