Quaternary tryptammonium salts: N, N-dimethyl- N- n-propyl-tryptammonium (DMPT) iodide and N-allyl- N, N-di-methyl-tryptammonium (DMALT) iodide

Acta Crystallogr E Crystallogr Commun. 2020 Jul 24;76(Pt 8):1357-1360. doi: 10.1107/S2056989020010014. eCollection 2020 Aug 1.

Abstract

The solid-state structures of two quaternary trytpammonium salts, namely, N,N-dimethyl-N-n-propyl-tryptammonium (DMPT) iodide [systematic name: 2-(1H-indol-3-yl)-N,N-dimethyl-N-propyl-aza-nium iodide], C15H23N2 +·I-, and N-allyl-N,N-di-methyl-tryptammonium (DMALT) iodide, [systematic name: 2-(1H-indol-3-yl)-N,N-dimethyl-N-(prop-2-en-1-yl)aza-nium iodide], C15H21N2 +·I-, are reported. Both salts possess a tri-alkyl-tryptammonium cation and an iodide anion in the asymmetric unit, which are joined together through N-H⋯I inter-actions. 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; hydrogen bonding; indoles; tryptamines.

Grants and funding

This work was funded by National Science Foundation, Directorate for Mathematical and Physical Sciences grant CHE-1429086.