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

Andrew R Chadeayne,David R Manke,Duyen N K Pham,James A Golen

doi:10.1107/s2056989020010014

Andrew R Chadeayne, David R Manke + Show 2 more

Open Access

https://doi.org/10.1107/s2056989020010014

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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.

Highlights

Quaternary tryptammonium salts have been observed in nature going back to 1934 when bufotenidine, the N-trimethyl analogue of serotonin, was discovered in the excretions of toads (Wieland et al, 1934)
The tryptamines of ‘magic mushrooms’ have garnered a great deal of interest of late as their psychotropic activity is being explored for the treatment of mental disorders including depression and anxiety (Johnson & Griffiths, 2017; Daniel & Haberman, 2017)
The other most closely related structures reported are of the N,N,N-trimethyl derivative of tryptophan – hypaphorine

Summary

Chemical context

Quaternary tryptammonium salts have been observed in nature going back to 1934 when bufotenidine, the N-trimethyl analogue of serotonin, was discovered in the excretions of toads (Wieland et al, 1934). The recent synthesis of aeruginascin (Sherwood, et al 2020) and its active metabolite, 4-hydroxyN,N,N-trimethyltryptamine (Chadeayne, Pham, Reid et al, 2020), as well as the biosynthetic production of both (Milne et al, 2020) further demonstrate the attention that these molecules have received. To this end, we sought to explore new quaternary tryptammonium salts, and the syntheses and structures of N,N-dimethyl-N-n-propyltryptammonium (DMPT) iodide and N-allyl-N,N-dimethyltryptammonium (DMALT) iodide are reported

Structural commentary

Supramolecular features

Synthesis and crystallization

Database survey