Identification of phase-I and phase-II metabolites and the metabolic pathway of the novel synthetic cannabinoid 5F-EDMB-PICA in vitro.

5F-EDMB-PICA is a newly emerged synthetic cannabinoid which has been characterized in relevant literature in recent years. Although phase-I metabolites of 5F-EDMB-PICA have been partly reported, the phase-II metabolism of this synthetic cannabinoid has not been studied yet. In this study, we established a phase-I and phase-II metabolism model in vitro by using pooled human liver microsomes, NADPH regeneration system, and UGT incubation system, with 1 mg/ml 5F-EDMB-PICA added and incubated at 37 °C for 60 min. The metabolites were analyzed by Q Exactive™ Hybrid Quadrupole-Orbitrap™ Mass Spectrometer, via which we discovered and identified 14 phase-I metabolites and 4 phase-II metabolites of 5F-EDMB-PICA, involving pathways such as ester hydrolysis, dehydrogenation, hydrolytic defluorination, hydroxylation, dihydroxylation, glucuronidation, and combinations of the pathways mentioned above. We recommend considering the monohydroxylation metabolites (M9, M10) with higher content and intact ester and 5-fluoropentyl structures as potential biomarkers of 5F-EDMB-PICA.

Identification and characterization of novel synthetic cannabinoid ethyl-2-(1-(5-fluoropentyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate (5F-EDMB-PICA).

PURPOSE: The purpose of the current study was to evaluate an analytical characterization of a novel synthetic cannabinoid ethyl-2-(1-(5-fluoropentyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate (5F-EDMB-PICA), which has a similar chemical structure to the controlled synthetic cannabinoid 5F-MDMB-PICA. METHODS: The compound was analyzed by gas chromatography-mass spectrometry (GC-MS), supercritical fluid chromatography-quadrupole time-of-flight-mass spectrometry (SFC-QTOF-MS) and spectroscopic methods, such as attenuated total reflection (ATR)-Fourier transform infrared (FTIR), ultraviolet-visible (UV-VIS) and nuclear magnetic resonance (NMR) spectroscopies. RESULTS: In this study, we reported a comprehensive analytical data of 5F-EDMB-PICA. The data of analytical characterization for the 5F-EDMB-PICA were obtained by GC-MS, SFC-QTOF-MS, ATR-FTIR spectroscopy, UV-VIS spectroscopy, and 1H and 13C NMR spectroscopy. CONCLUSIONS: In this study, we presented a comprehensive analytical characterization of 5F-EDMB-PICA obtained by 1H NMR, 13C NMR, GC-MS, SFC-QTOF-MS, ATR-FTIR spectroscopy and UV-VIS spectroscopy. The analytical data of 5F-EDMB-PICA are very useful for forensic, toxicological, and clinical diagnosis.

[Identification of Synthetic Cannabinoid 5F-EDMB-PICA in Suspicious Herbal Products].

ABSTRACT: Objective To study the qualitative analysis strategy for unknown synthetic cannabinoid in the suspicious herbal product when no reference substance is available. Methods The synthetic cannabinoid in herbal blend was extracted with methanol. The extract was concentrated by rotary evaporator and separated and purified by preparative liquid chromatography, to obtain high purity synthetic cannabinoid sample. Gas chromatography-mass spectrometry （GC-MS）, ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry （UPLC-QTOF-MS） and nuclear magnetic resonance （NMR） were used to determine the structure of the prepared compound. Results High purity unknown sample （10 mg） was obtained by preparative liquid chromatography. The sample was analyzed by GC-MS, UPLC-TOF-MS and NMR, and through spectrum analysis, the unknown synthetic cannabinoid was determined as 5F-EDMB-PICA. Conclusion The method to extract unknown synthetic cannabinoid from low content herbal products by preparative liquid chromatography was established, and the structure of the unknown sample was identified by comprehensive use of GC-MS, UPLC-QTOF-MS and NMR. The information will assist forensic laboratories in identifying this substance or other compounds with similar structures in their casework.

Identification of Synthetic Cannabinoid 5F-EDMB-PICA in Suspicious Herbal Products / 法医学杂志

Objective To study the qualitative analysis strategy for unknown synthetic cannabinoid in the suspicious herbal product when no reference substance is available. Methods The synthetic cannabinoid in herbal blend was extracted with methanol. The extract was concentrated by rotary evaporator and separated and purified by preparative liquid chromatography, to obtain high purity synthetic cannabinoid sample. Gas chromatography-mass spectrometry （GC-MS）, ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry （UPLC-QTOF-MS） and nuclear magnetic resonance （NMR） were used to determine the structure of the prepared compound. Results High purity unknown sample （10 mg） was obtained by preparative liquid chromatography. The sample was analyzed by GC-MS, UPLC-TOF-MS and NMR, and through spectrum analysis, the unknown synthetic cannabinoid was determined as 5F-EDMB-PICA. Conclusion The method to extract unknown synthetic cannabinoid from low content herbal products by preparative liquid chromatography was established, and the structure of the unknown sample was identified by comprehensive use of GC-MS, UPLC-QTOF-MS and NMR. The information will assist forensic laboratories in identifying this substance or other compounds with similar structures in their casework.