Abstract
The solid-state structures of the naturally occurring psychoactive tryptamine norpsilocin {4-hy-droxy-N-methyl-tryptamine (4-HO-NMT); systematic name: 3-[2-(methyl-amino)-eth-yl]-1H-indol-4-ol}, C11H14N2O, and its fumarate salt (4-hy-droxy-N-methyl-tryptammonium fumarate; systematic name: bis-{[2-(4-hy-droxy-1H-indol-3-yl)eth-yl]methyl-aza-nium} but-2-enedioate), C11H15N2O+·0.5C4H2O4 2-, are reported. The freebase of 4-HO-NMT has a single mol-ecule in the asymmetric unit joined together by N-H⋯O and O-H⋯O hydrogen bonds in a two-dimensional network parallel to the (100) plane. The ethyl-amine arm of the tryptamine is modeled as a two-component disorder with a 0.895 (3) to 0.105 (3) occupancy ratio. The fumarate salt of 4-HO-NMT crystallizes with a tryptammonium cation and one half of a fumarate dianion in the asymmetric unit. The ions are joined together by N-H⋯O and O-H⋯O hydrogen bonds to form a three-dimensional framework, as well as π-π stacking between the six-membered rings of inversion-related indoles (symmetry operation: 2-x, 1-y, 2 - z).
Highlights
The solid-state structures of the naturally occurring psychoactive tryptamine norpsilocin {4-hydroxy-N-methyltryptamine (4-HO-NMT); systematic name: 3-[2-(methylamino)ethyl]-1H-indol-4-ol}, C11H14N2O, and its fumarate salt (4-hydroxy-N-methyltryptammonium fumarate; systematic name: bis{[2-(4-hydroxy-1H-indol-3-yl)ethyl]methylazanium} but-2-enedioate), C11H15N2O+Á0.5C4H2O42À, are reported
The freebase of 4-HO-NMT has a single molecule in the asymmetric unit joined together by N—HÁ Á ÁO and O—HÁ Á ÁO hydrogen bonds in a two-dimensional network parallel to the (100) plane
The indole ring system of the Despite rapidly growing evidence supporting psilocin/ psilocybin’s potential for treating mood disorders, very little work has been done to investigate the properties of other structurally similar compounds found in magic mushrooms, e.g. norpsilocin/baeocystin
Summary
Psychoactive tryptamines, psilocybin and psilocin, have recently garnered a great deal of interest because of their potential to treat disorders including anxiety, addiction, and depression (Johnson & Griffiths, 2017; Carhart-Harris & Goodwin, 2017). Psilocybin was recently granted the ‘breakthrough therapy’ designation by the US Food and Drug Administration (Feltman, 2019) To this point, the focus of research on psychedelics in therapy has largely been on psilocybin and psilocin. The focus of research on psychedelics in therapy has largely been on psilocybin and psilocin Despite this focus, there are more than 200 species of ‘magic mushrooms’ containing many different psychoactive tryptamines and combinations of the same (Stamets, 1996). Baeocystin, the monomethyl analog of psilocybin, is the second most abundant naturally occurring tryptamine found in ‘magic mushrooms’. When tested as an agonist at the human seratonin 2a receptor, synthetic norpsilocin was as potent, if not more so, compared to psilocin (Sherwood et al, 2020)
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