Psilocin (4-hydroxy-N,N-dimethyltryptamine, 4-HO-DMT) and bufotenine (5-hydroxy-N,N-dimethyltryptamine, 5-HO-DMT), which are both naturally occurring compounds, are classified as controlled substances in numerous countries due to their pharmacological activities and recreational usage. There are two other benzene ring regioisomers, 6-hydroxy-N,N-dimethyltryp...
One among four people in the world are affected by mental or neurological illness at some point of their lives. An estimated number of 450 million people suffers from neurological disorders of one or the other type making mental disorders as the leading cause for disability across the globe. Under psychosis and depression maintenance therapy drug acting on D...
Abstract Upon injury, psychotropic psilocybin-producing mushrooms instantly develop an intense blue color, the chemical basis and mode of formation of which has remained elusive. We report two enzymes from Psilocybe cubensis that carry out a two-step cascade to prepare psilocybin for oxidative oligomerization that leads to blue products. The phosphatase PsiP...
Abstract The psychotropic effects of Psilocybe “magic” mushrooms are caused by the l -tryptophan-derived alkaloid psilocybin. Despite their significance, the secondary metabolome of these fungi is poorly understood in general. Our analysis of four Psilocybe species identified harmane, harmine, and a range of other l -tryptophan-derived β-carbolines as their ...
The solid-state structures of the salts of two substituted tryptamines, namely N -isopropyl- N -methyltryptaminium (MiPT) fumarate {systematic name: [2-(1 H -indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate}, C14 H21 N2 + ·C4 H3 O4 −, and 4-hydroxy- N -isopropyl- N -methyltryptaminium (4-HO-MiPT) fumarate monohydrate {systematic name: [2-(4...
Psilocybin and its direct precursor baeocystin are indole alkaloids of psychotropic Psilocybe mushrooms. The pharmaceutical interest in psilocybin as a treatment option against depression and anxiety is currently being investigated in advanced clinical trials. Here, we report a biocatalytic route to synthesize 6-methylated psilocybin and baeocystin from 4-hy...
The title compound (systematic name: bis{2-[4-(acetyloxy)-1 H -indol-3-yl]ethan-1-aminium} but-2-enedioate), 2C 14 H19 N2 O2 + ·C4 H2 O4 2−, has a single protonated psilacetin cation and one half of a fumarate dianion in the asymmetric unit. There are N-H...O hydrogen bonds between the ammonium H atoms and the fumarate O atoms, as well as N-H...O hydrogen bo...
Abstract Psilocybin ist der psychotrope, vom Tryptamin abgeleitete Naturstoff der Psilocybe-Fruchtkörper, der so genannten “Zauberpilze”. Obwohl dessen Struktur seit 60 Jahren bekannt ist, blieb die enzymatische Grundlage ihrer Biosynthese ungeklärt. Wir charakterisierten vier Psilocybin-Biosyntheseenzyme, nämlich i) PsiD, welches zu einer neuen Klasse pilzl...
A rapid new spectrophotometric method is developed for the determination of psilocin and psilocybin using the oxidative coupling reaction with 3-methylbenzthiazolinone-2-hydrazone. The method is precise and accurate. It can be applied to the estimation of psilocin and psilocybin in forensic exhibits. Keywords: 3-methylbenzthiazolinone-2-hydrazone, psilocin, ...
Objective To explore the effects of flavone glycoside on psilocybin-induced oxidative damage in rats.Methods Five group Sprague-Dawley rats(10 for each group) were received vehicle(Con),low dose of psilocybin(i.p.,0.5 μg/kg body weight)(LD),high dose of psilocybin(i.p.,1.5 μg/kg body weight)(HD),low dose of psilocybin(i.p.) plus flavone glycoside(i.p.100 mg/...
Indole alkaloids of Psilocybe cubensis have been reported to be the potential candidates for drug discovery in central nervous system (CNS) disorders. In this research, the effect of the harvesting light on increasing the active alkaloids of P. cubensis was investigated. Three different lighting conditions, that is, dim daylight, indirect daylight, and darkn...
The content of tryptamine derivatives in Psilocybe semilanceata, a popular hallucinogenic mushroom, was measured by high-performance liquid chromatography. Most of the 52 samples have been collected at several localities in Switzerland during a 1-5 year period. The content of psilocybin and baeocystin varied in the range of 0.21-2.02% and 0.05-0.77%, respect...
Abstract Baeocystin ( 7 ) (4-phosphoryloxy-N-methyltryptamine) has been synthesized starting from 2-methyl-3-nitrophenol ( 1 ). The spectral data (UV, IR, 1 H-, 31 P-, 13 C-NMR, MS) are identical with those of 7 isolated from Psilocybe semilanceata.
The nature of the stereochemistry and aromatic ring substituents and their importance to biological activity for phenethylamine-type hallucinogens is presented. The possibility of a hydrophobic site to bind to the 4-substituent and its likely geometry is described. A brief discussion of the structure-activity relationships for tryptamines such as psilocin an...
The crystal structure of psilocybin, the major hallucinogenic component of Teonanácatl, the sacred mushroom of Mexico, has been determined in crystals of the monomethanolate. Crystals are monoclinic, space group P21/c, a= 1264(1), b= 2911(2), c= 884·7(6) pm, β= 107·37(2)°, and contain two molecules of psilocybin and two molecules of methanol of solvation per...
(1960). Production of Cross-Tolerance to Psychosis-Producing Doses of Lysergic Acid Diethylamide and Psilocybin. The Journal of Psychology: Vol. 49, No. 1, pp. 151-154.
Abstract Various modifications were made in the molecular structure of the natural psychotropic substances psilocybin (I) and psilocin (11) to obtain an insight into the relationship between structure and psychotropic action of this group of substances. A description is given of the synthesis and properties of the position isomers of I and II with a phosphor...
