Abstract
The title compound, bis-(N,N-diallyl-5-meth-oxy-tryptammonium) (5-MeO-DALT) fumarate (systematic name: bis-{N-[2-(5-meth-oxy-1H-indol-3-yl)eth-yl]- N-(prop-2-en-1-yl)prop-2-en-1-aminium} (E)-but-2-enedioate), 2C17H23N2O+·C4H2O4 2-, 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 [111].
Highlights
The title compound, bis(N,N-diallyl-5-methoxytryptammonium) (5-MeODALT) fumarate (systematic name: bis{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]N-(prop-2-en-1-yl)prop-2-en-1-aminium} (E)-but-2-enedioate), 2C17H23N2O+ÁC4H2O42À, has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit
Psychotropic compounds have gained a lot of attention in recent years for their potential as therapeutics to treat depression, anxiety, post-traumatic stress disorder, and addiction, among other disorders (Nichols & Hendricks, 2020). 5-Methoxy-N,N-dimethyltryptamine (5-MeO-DMT) is a naturally occurring tryptamine found in the parotid gland of some toads, and this compound has been explored for its clinical effects in treating mood disorders (Davis et al, 2018). 5-MeO-DMT is highly active at the serotonin (5-hydroxytryptamine, 5-HT) 2A receptor, which is the origin of its psychotropic activity
E77, 416–419 research communications shows activity at a number of serotonin receptors, including 5-HT1A, 5-HT1D, 5-HT2A, 5-HT2B, 5-HT6 and 5-HT7 (Cozzi & Daley, 2016). As this class of molecules become more significant in the treatment of mood disorders, it is important to have analytically pure, well-characterized, crystalline material to study the unique impact of individual compounds from the diverse range of compounds
Summary
Psychotropic compounds have gained a lot of attention in recent years for their potential as therapeutics to treat depression, anxiety, post-traumatic stress disorder, and addiction, among other disorders (Nichols & Hendricks, 2020). 5-Methoxy-N,N-dimethyltryptamine (5-MeO-DMT) is a naturally occurring tryptamine found in the parotid gland of some toads, and this compound has been explored for its clinical effects in treating mood disorders (Davis et al, 2018). 5-MeO-DMT is highly active at the serotonin (5-hydroxytryptamine, 5-HT) 2A receptor, which is the origin of its psychotropic activity. E77, 416–419 research communications shows activity at a number of serotonin receptors, including 5-HT1A, 5-HT1D, 5-HT2A, 5-HT2B, 5-HT6 and 5-HT7 (Cozzi & Daley, 2016) As this class of molecules become more significant in the treatment of mood disorders, it is important to have analytically pure, well-characterized, crystalline material to study the unique impact of individual compounds from the diverse range of compounds. It is important to explore the effects of analytically pure combinations of these compounds to explore potential entourage effects To best administer these compounds orally active, water-soluble crystalline materials are ideal. We set out to synthesize a water-soluble salt of 5-MeO-DALT, and report the synthesis and structure of bis(5-methoxy-N,N-diallyltryptammonium) fumarate . The nature of this salt allows for it to have high solubility in water, while the freebase does not
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