Isolation and structure of coprine, the in vivo aldehyde dehydrogenase inhibitor in Coprinus atramentarius; syntheses of coprine and related cyclopropanone derivatives

Abstract

The disulphiram-like principle of the inky cap mushroom Coprinus atramentarius has been identified as N5-(1-hydroxycyclopropyl)-L-glutamine (coprine)(1). Coprine (1) and several analogous compounds have been synthesised by N-acylation of the unstable 1-aminocyclopropanol, generated in situ from 1-hydroxycyclopropyl-ammonium chloride (6). The lower 1-alkoxycyclopropylamines are stable, distillable compounds which can be N-acylated. Many of the 1-aminocyclopropanol derivatives synthesised have the same physiological activity as coprine.