Bis(4-hy-droxy-N-isopropyl-N-methyl-trypt-ammo-nium) fumarate: a new crystalline form of miprocin.

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

doi:10.1107/s2056989020002923

Andrew R Chadeayne, Duyen N K Pham + Show 2 more

Open Access

https://doi.org/10.1107/s2056989020002923

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Abstract

The title compound, bis-(4-hy-droxy-N-isopropyl-N-methyl-tryptammonium) (4-HO-MiPT) fumarate (systematic name: bis-{[2-(4-hy-droxy-1H-indol-3-yl)eth-yl](meth-yl)propan-2-yl-aza-nium} but-2-enedioate), 2C14H21N2O+·C4H2O4 2-, has a singly protonated tryptammonium cation and one half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by N-H⋯O and O-H⋯O hydrogen bonds. These chains are a combination of R 4 2(20) rings, and C 2 2(15) and C 4 4(30) parallel chains along (110). They are further consolidated by N-H⋯π inter-actions. There are two two-component types of disorder impacting the tryptammonium fragment with a 0.753 (7):0.247 (7) occupancy ratio and one of the fumarate oxygen atoms with a 0.73 (8):0.27 (8) ratio.

Highlights

A wide variety of naturally occurring organisms, including over 200 species of ‘magic’ mushrooms, contain psychoactive tryptamine compounds (Stamets, 1996)
We reported the structure of 4-acetoxy-N,N-dimethyl tryptamine (4-AcO-DMT) fumarate, which is a synthetic analogue of psilocybin
In a report last year, we presented the first structure of 4-HO-MiPT (Chadeayne, Pham et al, 2019a), which crystallizes as the hydrofumarate monohydrate

Summary

Chemical context

A wide variety of naturally occurring organisms, including over 200 species of ‘magic’ mushrooms, contain psychoactive tryptamine compounds (Stamets, 1996). Of these compounds, psilocybin has received the most scientific and commercial attention because of recent studies demonstrating its potential for treating mood disorders including addiction, anxiety, depression and PTSD (Johnson & Griffiths, 2017; CarhartHarris & Goodwin, 2017). We reported the structure of 4-acetoxy-N,N-dimethyl tryptamine (4-AcO-DMT) fumarate, which is a synthetic analogue of psilocybin. In a report last year, we presented the first structure of 4-HO-MiPT (Chadeayne, Pham et al, 2019a), which crystallizes as the hydrofumarate monohydrate. The solid state structure of the new salt is presented here

Structural commentary

Supramolecular features

Database survey

Synthesis and crystallization

Refinement