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.

Fatalities implicating psychedelic mushrooms are not a common clinical situation in everyday forensic medicine. Despite classification as an illegal drug in many countries, psilocybin mushrooms have the reputation of being safe. We report the case of a young man who jumped from a second story balcony under the influence of psilocybin mushrooms. The psilocin assay was performed by gas chromatography coupled to an electron-impact ionization time-of-flight detector (GC-EI-TOF) after solid-phase extraction. Total psilocin was quantified in peripheral and cardiac blood as 60 and 67 ng/mL, respectively, and in urine (2230 ng/mL), bile (3102 ng/mL), and vitreous humor (57 ng/mL). This case report and review of literature highlights the danger of psilocybin mushrooms. Isolated use of psilocybin mushrooms by a regular consumer without psychiatric history, even under \"safe\" circumstances, can lead to a fatal outcome.