Abstract
The solid-state structure of the bufotenine derivative bis-(5-meth-oxy-2,N,N-tri-methyl-tryptammonium) (5-MeO-2-Me-DMT) fumarate (systematic name: bis-{[2-(5-meth-oxy-2-methyl-1H-indol-3-yl)eth-yl]di-methyl-aza-nium} (2E)-but-2-enedioate), 2C14H21N2O+·C4H2O4 2-, the bufotenidine derivative 5-meth-oxy-2,N,N,N-tetra-methyl-tryptammonium (5-MeO-2-Me-TMT) iodide {systematic name: [2-(5-meth-oxy-2-methyl-1H-indol-3-yl)eth-yl]tri-methyl-aza-nium iodide}, C15H23N2O+·I-, and the hydrate of the same {systematic name: [2-(5-meth-oxy-2-methyl-1H-indol-3-yl)eth-yl]tri-methyl-aza-nium iodide monohydrate}, C15H23N2O+·I-·H2O, are reported. The structure of 5-MeO-2-Me-DMT fumarate possesses one tryptammonium cation and a half of a fumarate dianion in the asymmetric unit, linked together by N-H⋯O hydrogen bonds in infinite two-dimensional networks parallel to the (101) plane. The structure of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation and one iodide anion in the asymmetric unit. The ions are linked via N-H⋯I hydrogen bonds, and indoles are coupled in dimers through π-π inter-actions. The hydrate of 5-MeO-2-Me-TMT iodide possesses one tryptammonium cation, one iodide anion and one water mol-ecule in the asymmetric unit. It shows N-H⋯I and O-H⋯I hydrogen bonds that couple the tryptammonium cations into dimers.
Highlights
Bufotenine, the N,N-dimethyl analogue of serotonin, and bufotenidine, the N,N,N-trimethyl analogue of serotonin, were both identified in toad secretions in 1934 (Wieland et al, 1934)
A detailed synthesis of the freebase of the compound was reported by Alexander Shulgin, who described its clinical effects on humans, with psychotropic activity occurring within an hour of oral consumption accompanied by physical stimulation (Shulgin & Shulgin, 2016)
We report the synthesis of 5-methoxy-2,N,N,N-tetramethyltryptammonium iodide, along with its structure
Summary
Bufotenine, the N,N-dimethyl analogue of serotonin, and bufotenidine, the N,N,N-trimethyl analogue of serotonin, were both identified in toad secretions in 1934 (Wieland et al, 1934) These and other indoalkylamines found in the paratoid glands of Bufo alvarius toads can lead to psychotropic activity in humans and other animals. The methylation of the 2-position provides oral activity in 5-MeO-2-MeDMT, likely by limiting its decomposition by monoamineoxidases, and appears to reduce activity at the 5-HT2A receptor, making it significantly less active than inhaled 5-MeO-DMT Bioassays of this compound have shown it to be an agonist for the serotonin 5-HT6 receptor (Ki = 89 nM) (Glennon, et al 2000) and the serotonin 5-HT7 receptor (Ki = 1,120 nM) (Vermeulen, et al 2003). We report the structure of the first solvate of 5-methoxy-2,N,N,Ntetramethyltryptammonium iodide as its hydrate
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