The Psilocin (4‐hydroxy‐N,N‐dimethyltryptamine) and Bufotenine (5‐hydroxy‐N,N‐dimethyltryptamine) Case: Ensuring the Correct Isomer has Been Identified

Abstract

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‐dimethyltryptamine (6‐HO‐DMT) and 7‐hydroxy‐N,N‐dimethyltryptamine (7‐HO‐DMT), which are not classified by name as controlled substances, and which were synthesized for this current work. The four isomers were analyzed using routine methodologies employed by the Israel's Police Division of Identification and Forensic Science (DIFS) Laboratory, namely thin layer chromatography (TLC), Fourier transform infrared spectroscopy (FTIR), and gas chromatography mass spectroscopy (GC‐MS). It was found possible to differentiate the four isomers. Forensic specimens that were suspected to be psilocybe mushrooms were examined, confirming that it is now possible to unequivocally identify the presence of psilocin and rule out the presence of its other isomers.

Anti-Inflammatory Activity of an Indole Alkaloid Isolated from Bebuas (Premna serratifolia)

“…On the basis of phytochemical screening results, physical form, the spectrum data of UV, IR and by the literature comparism, the main components from the isolated ethanolic leaves extract of P. serratifolia leaves could be inferred to be bufotenine, as seen formerly in literatures [31], [32], [33]. This further strengthens the notion that the isolate was a compound with a basic skeleton such as bufotenine.…”

“…The assumption that the isolate was a compound with characters like bufotenine was also supported by the similarities of their physical form. Bufotenine was a yellow crystals that could transform to yellow oil after oxidized by air exposure [31], [32], [33]. This was in accordance with the physical form of the isolate that was yellowish crystals when it was freshly dried from the solvent, but after being exposed for a long time by air, the isolate transformed to yellow oil due to oxidizing process [33].…”

Interpol Review of Drug Analysis 2019-2022

“…2019 review [ 435 ]; morphological, chemical, and genetic analysis of mycelia of psychedelic fungi collected from a clandestine laboratory using scanning electron microscopy (SEM), mass spectrometry, HRM analysis, and internal transcribed spacer (ITS) sequencing [ 436 ]; 2020 use of TLC, FTIR and GC-MS to differentiate Psilocin (4-hydroxy-N,N-dimethyltryptamine, 4-HO-DMT) and bufotenine (5-hydroxy-N,N-dimethyltryptamine, 5-HO-DMT) and benzene ring regioisomers, 6-hydroxy-N,N-dimethyltryptamine (6-HO-DMT) and 7-hydroxy-N,N-dimethyltryptamine (7-HO-DMT) [ 437 ]; immunochemical detection method for monitoring psilocybin and psilocin in dried powder of hallucinogenic mushroom (Psilocybe cubensis) [ 438 ]; 2021 chemoenzymatic synthesis of 5-methylpsilocin, a novel analogue of psilocybin with potential psychedelic activity [ 439 ]; stability study of psilocybin and its four analogues (psilocin, baeocystin, norbaeocystin, and aeruginascin) in psilocybe cubensis mushrooms [ 440 ]; medicinal properties and bioactive compounds from 79 species of wild mushrooms native to North America [ 441 ]; DNA-based identification of hallucinogenic mushrooms [ 442 ]; forensic detection method for hallucinogenic mushrooms via High-Resolution Melting (HRM) analysis [ 443 ]; 2022 phytochemicals and antioxidant activity of seven wild mushrooms [ 444 ].…”

Mycotherapy: Potential of Fungal Bioactives for the Treatment of Mental Health Disorders and Morbidities of Chronic Pain

“…Bufotenine (5-HO-DMT) is an alkaloid and a substituted tryptamine similar to serotonin and psilocin, also present in the Amanita mushroom. As such, it has the ability to cross the BBB having agonistic effects on 5-HT1A and 5-HT1B receptors [ 114 ]. Another substituted tryptamine,5-MeO-DMT, requires enzymatic activity of a monoamine oxidase (MAO) inhibitor to induce its psychedelic effects orally [ 48 ].…”