title: Synthesis, hydrolysis and stability of psilocin glucuronide.
abstract: A two-step synthesis of psilocin glucuronide (PCG), the main metabolite of psilocin, with methyl 2,3,4-tri-O-isobutyryl-1-O-trichloroacetimidoyl-α-d-glucopyranuronate is reported. With the synthesized PCG, hydrolysis conditions in serum and urine were optimized. Escherichia coli proved to be a better enzyme source for β-glucuronidase than Helix pomatia. It was essential to add ascorbic acid to serum samples to protect psilocin during incubation. Furthermore the stability of PCG and psilocin was compared as stability data are the basis for forensic interpretation of measurements. PCG showed a greater long-term stability after six months in deep frozen serum and urine samples than psilocin. The short-term stability of PCG for one week in whole blood at room temperature and in deep frozen samples was also better than that of psilocin. Therefore, PCG can be considered to be more stable than the labile psilocin and should always be included if psilocin is analyzed in samples.
authors: Institute of Legal Medicine, University Hospital Münster, Röntgenstr. 23, D-48149 Münster, Germany. Electronic address: rafaela.martin@uni-muenster.de.
authors: Rafaela
authors: R
authors: Martin
authors: Institute of Legal Medicine, University Hospital Münster, Röntgenstr. 23, D-48149 Münster, Germany. Electronic address: jennifer.schuerenkamp@ukmuenster.de.
authors: Jennifer
authors: J
authors: Schürenkamp
authors: Institute of Legal Medicine, University Hospital Münster, Röntgenstr. 23, D-48149 Münster, Germany. Electronic address: heidi.pfeiffer@ukmuenster.de.
authors: Heidi
authors: H
authors: Pfeiffer
authors: Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Corrensstr. 48, D-48149 Münster, Germany. Electronic address: lehrm@uni-muenster.de.
authors: Matthias
authors: M
authors: Lehr
authors: Institute of Legal Medicine, University Hospital Münster, Röntgenstr. 23, D-48149 Münster, Germany. Electronic address: helga.koehler@ukmuenster.de.
authors: Helga
authors: H
authors: Köhler
mesh_terms: D004355:Drug Stability; D005615:Freezing; D005966:Glucuronidase / Q000737:chemistry; D020719:Glucuronides / Q000737:chemistry*; D006213:Hallucinogens / Q000737:chemistry*; D006801:Humans; D006868:Hydrolysis; D015394:Molecular Structure; D011562:Psilocybin / Q000031:analogs & derivatives* / Q000737:chemistry; D013048:Specimen Handling
chemical_list: D020719:Glucuronides; D006213:Hallucinogens; C000602874:psilocin glucuronide; D011562:Psilocybin; C009105:psilocin; D005966:Glucuronidase
keywords: Hydrolysis; Psilocin glucuronide; Stability; Synthesis; β-Glucuronidase