The Psilocin (4-hydroxy-N,N-dimethyltryptamine) and Bufotenine (5-hydroxy-N,N-dimethyltryptamine) Case: Ensuring the Correct Isomer has Been Identified.
Tehila Mishraki-Berkowitz, Esti Kochelski, Pierce Kavanagh, John O'Brien, Clodagh Dunne, Brian Talbot, Patricia Ennis, Udi Ehud Wolf
Journal of forensic sciences September 1, 2020 DOI: 10.1111/1556-4029.14368 via PubMed
Summary
AI-generated from the abstractPsilocin and bufotenine are naturally occurring controlled substances, while two other isomers (6-HO-DMT and 7-HO-DMT) are not classified as controlled substances. The four isomers were synthesized and analyzed using thin layer chromatography, Fourier transform infrared spectroscopy, and gas chromatography mass spectroscopy. The methods successfully differentiated all four isomers. Analysis of forensic specimens suspected to be psilocybe mushrooms confirmed that psilocin can be unequivocally identified and its other isomers ruled out, providing accurate identification for forensic investigations.
Study at a glance
| Characteristics | Method development and validation study Peer reviewed |
|---|---|
| Population | Forensic specimens suspected to be psilocybe mushrooms |
| Topics | Psilocybin |
| Keywords | Bufotenine Controlled substances Hydroxy-N,N-Dimethyltryptamine Ho-DMT Positional isomers |
| Citations | 12 |
| Key finding | Routine forensic techniques (TLC, FTIR, GC-MS) can unequivocally differentiate psilocin and bufotenine from their non-controlled positional isomers, enabling accurate identification in seized drug specimens. |
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.