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Identification of urinary metabolites of the synthetic cannabinoid 5F-CUMYL-P7AICA in human casework

Staeheli, Sandra N., Steuer, Andrea E., Kraemer, Thomas
Forensic science international 2019 v.294 pp. 76-79
biotransformation, cannabinoids, carboxylation, humans, in vitro studies, liquid chromatography, markets, mass spectrometry, metabolism, metabolites, moieties, monitoring, psychotropic agents, urine
Synthetic cannabinoids belong to one of the largest groups of new psychoactive substances (NPS) and are challenging regarding analytical detection because of the often complete metabolic degradation of the parent compounds. 5F-CUMYL-P7AICA contains a 7-azaindole moiety and appeared first on the market in 2015. In the frame of abstinence control cases, possible 5F-CUMYL-P7AICA metabolites were detected in three urine samples. The samples were reanalyzed using liquid-chromatography-high resolution mass spectrometry (LC-HRMS) and human phase I and II metabolites were identified. Major in vivo biotransformation steps of 5F-CUMYL-P7AICA in humans were oxidative defluorination followed by carboxylation, and monohydroxylation followed by sulfation and glucuronidation. Evaluation of the metabolites as marker for 5F-CUMYL-P7AICA consumption revealed the defluorinated and carboxylated metabolite to be important for sensitive detection. For higher specificity, additional monitoring of a monohydroxylated metabolite is recommended. Comparison with previously published in vitro metabolism data revealed good accordance of the results, with exception of a of the dihydroxylated metabolites from the in vitro assays, which were not detected in the in vivo samples.