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Phase I metabolism of the recently emerged synthetic cannabinoid CUMYL‐PEGACLONE and detection in human urine samples
Author(s) -
Mogler Lukas,
Wilde Maurice,
Huppertz Laura M.,
Weinfurtner Georg,
Franz Florian,
Auwärter Volker
Publication year - 2018
Publication title -
drug testing and analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.065
H-Index - 54
eISSN - 1942-7611
pISSN - 1942-7603
DOI - 10.1002/dta.2352
Subject(s) - metabolite , chemistry , synthetic cannabinoids , chromatography , urine , in vivo , cannabinoid , designer drug , drug metabolism , tandem mass spectrometry , microsome , indole test , mass spectrometry , metabolism , in vitro , drug , pharmacology , biochemistry , medicine , biology , receptor , microbiology and biotechnology
Indole‐, indazole‐, or azaindole‐based synthetic cannabinoids (SCs), bearing a cumyl substituent are a widespread, recreationally used subgroup of new psychoactive substances (NPS). The latest cumyl‐derivative, CUMYL‐PEGACLONE, emerged in December 2016 on the German drug market. The substance features a novel γ ‐carboline core structure, which is most likely synthesized to bypass generic legislative approaches to control SCs by prohibiting distinct core structures. Using liquid chromatography–tandem mass spectrometry and liquid chromatography–high resolution mass spectrometry techniques, the main in vivo phase I metabolites of this new substance were detected. A pooled human liver microsome assay was applied to generate in vitro reference spectra of CUMYL‐PEGACLONE phase I metabolites. Additionally, 30 urine samples were investigated leading to 22 in vivo metabolites. A metabolite mono‐hydroxylated at the γ ‐carbolinone core system and a metabolite with an additional carbonyl group at the pentyl side chain were evaluated as highly specific and sensitive markers to proof CUMYL‐PEGACLONE uptake. Moreover, 3 immunochemical assays commonly used for SC screening in urine were tested for their capability of detecting the new drug but failed due to insufficient cross‐reactivity.