Quaternary tryptammonium salts: N,N-dimethyl-N-n-propyltryptammonium (DMPT) iodide and N-allyl-N,N-dimethyltryptammonium (DMALT) iodide

Abstract

The solid-state structures of two quaternary trytpammonium salts, namely, N,N-dimethyl-N-n-propyltryptammonium (DMPT) iodide [systematic name: 2-(1H-indol-3-yl)-N,N-dimethyl-N-propylazanium iodide], C15H23N2+·I−, and N-allyl-N,N-dimethyltryptammonium (DMALT) iodide, [systematic name: 2-(1H-indol-3-yl)-N,N-dimethyl-N-(prop-2-en-1-yl)azanium iodide], C15H21N2+·I−, are reported. Both salts possess a trialkyltryptammonium cation and an iodide anion in the asymmetric unit, which are joined together through N—H...I interactions. The DMALT structure was refined as an inversion twin, and the allyl group is disordered over two orientations with a 0.70 (4):0.30 (4) ratio.

Keywords

• crystal structure
• tryptamines
• indoles
• hydrogen bonding