Abstract
The solid-state structures of the synthetic psychedelic 5-meth-oxy-N,N-di-n-propyl-tryptamine (5-MeO-DPT) {systematic name: N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-propyl-propan-1-amine}, C17H25N2O, and its fumarate salt, bis-(5-meth-oxy-N,N-di-n-propyl-tryptammonium) fumarate (systematic name: bis-{N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]-N-propyl-propan-1-aminium} but-2-ene-dio-ate), 2C17H25N2O+·C4H2O4 2-, are reported. The freebase has a single tryptamine mol-ecule in the asymmetric unit. The mol-ecules are linked together by N-H⋯N hydrogen bonds in zigzag chains along the [010] direction. The fumarate salt has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N-H⋯O hydrogen bonds. These chains are combinations of R 4 4(22) rings, and C 2 2(14) and C 4 4(28) parallel chains along [001].
Highlights
5-Methoxy-N,N-dimethyltryptamine (5-MeO-DMT) is a psychoactive indolealkylamine that is found in a number of plants and animals, but is best known to be present in the parotid glands of the Colorado River toad, Bufo alvarius (Shen et al, 2010). 5-MeO-DMT demonstrates high activity at the serotonin (5-hydroxytryptamine, 5-HT) 2A receptor, which leads to its psychotropic activity
There are a number of synthetic N,N-dialkyl derivatives including 5-methoxy-N-methyl-N-isopropyltryptamin (5-MeO-MiPT), 5-methoxy-N,N-diethyltryptamine (5-MeODET), 5-methoxy-N,N-di-n-propyltryptamine (5-MeO-DPT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DiPT)
Alexander Shulgin described the experience associated with inhalation of these derivatives in humans, with 5-MeO-DMT described as ‘positive and out-of-body’ while 5-MeO-DPT was described as ‘good and bad’ (Shulgin & Shulgin, 1997). 5-MeO-DPT has not been described much in the scientific literature, though a recent report described its activity at the 5-HT1A and 5-HT2A receptors showing 75–100% of full agonism at both receptors (Astrand et al, 2020)
Summary
5-Methoxy-N,N-dimethyltryptamine (5-MeO-DMT) is a psychoactive indolealkylamine that is found in a number of plants and animals, but is best known to be present in the parotid glands of the Colorado River toad, Bufo alvarius (Shen et al, 2010). 5-MeO-DMT demonstrates high activity at the serotonin (5-hydroxytryptamine, 5-HT) 2A receptor, which leads to its psychotropic activity. Recent research has pointed to 5-MeO-DMT as a promising pharmaceutical in the treatment of mental health disorders (Uthaug et al, 2019). 5-MeO-DPT has not been described much in the scientific literature, though a recent report described its activity at the 5-HT1A and 5-HT2A receptors showing 75–100% of full agonism at both receptors (Astrand et al, 2020). As this class of compounds becomes more important for the treatment of mental health in humans, an in depth understanding of these compounds and how the structural changes impact the clinical experience in humans is going to be significant.
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