Abstract
The title compound, 4-hy-droxy-N,N-di-n-propyl-tryptammonium (4-HO-DPT) chloride {systematic name: N-[2-(4-hy-droxy-1H-indol-3-yl)eth-yl]-N-propyl-propan-1-aminium chloride}, C16H25N2O+·Cl-, has a singly protonated trypt-ammonium cation and one chloride anion in the asymmetric unit. A series of N-H⋯Cl and O-H⋯Cl hydrogen bonds connect the ions together in ladder chains along [010].
Highlights
The title compound, 4-hydroxy-N,N-di-n-propyltryptammonium (4-HO-DPT) chloride {systematic name: N-[2-(4-hydroxy-1H-indol-3-yl)ethyl]-N-propylpropan-1-aminium chloride}, C16H25N2O+ÁClÀ, has a singly protonated tryptammonium cation and one chloride anion in the asymmetric unit
Which has been reported as its freebase (CCDC 1992279; Chadeayne et al, 2020b) and its fumarate salt (CCDC 1992278; Chadeayne et al, 2020b), and the active metabolite of aeruginascin À 4-hydroxy-N,N,N-trimethyltryptamine (XUXFAA; Chadeayne, Pham, Reid et al, 2020) which is reported as its iodide salt
The structure of the synthetic psychedelic 4-HOMiPT has been reported as its one-to-one hydrofumarate salt (RONSUL; Chadeayne et al, 2019a) and as its two-to-one fumarate salt (CCDC 1987588; Chadeayne et al, 2 2020a)
Summary
Psilocybin, N,N-dimethyl-4-phosphoryloxytryptamine, is a naturally occurring tryptamine found in ‘magic mushrooms’. The phosphate group of psilocybin is hydrolyzed to generate psilocin, 4-hydroxy-N,N-dimethyltryptamine. Psilocybin functions as a prodrug of psilocin, its active metabolite, which binds to and stimulates the human serotonin 2a receptor (Geiger et al, 2018), causing profound changes to human consciousness, which are generally described as a ‘psychedelic’ experience. Human serotonin 2a receptor agonists (e.g. LSD, ayahuasca/DMT, psilocybin/psilocin, peyote/mescaline, 5-MeO-DMT) have shown incredible potential for treating a wide variety of the world’s most debilitating, intractable, and costly health problems, including anxiety, depression, addiction, post-traumatic stress disorder (PTSD) and inflammation (Johnson & Griffiths, 2017; Carhart-Harris & Goodwin, 2017). 4-Hydroxy-N,N-di-n-propyltryptamine (4-HO-DPT) is a structural analogue of psilocin and produces similar (though not identical) psychedelic effects in human subjects (Shulgin & Shulgin, 2016).
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