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Human urinary metabolite pattern of a new synthetic cannabimimetic, methyl 2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate

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Abstract

A number of metabolites of a new synthetic cannabimimetic, which is a derivative of 2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoic acid, were identified in human urine. The parent compound, a methyl ester of this acid, was identified in seizures in persons from the same city where analysis of drug-intoxication urine samples revealed the presence of the compound’s metabolites. This compound named ‘MDMB-CHMICA’ was reported to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) via the Early Warning System (EWS) in 2014. Hydrolysis of the ester was found to be the main metabolic pathway followed by mono-, di- and tri-hydroxylation, ketone formation, ketone formation with monohydroxylation, dealkylation, and dealkylation combined with hydroxylation. Additionally, the products by internal dehydration of hydroxylated forms with lactone formation were detected. Mono-hydroxylated metabolites were detected from their glucuronidated forms. Identification of metabolites was made on the basis of gas chromatography–mass spectrometry and liquid chromatography with time-of-flight mass spectrometry and ion trap mass spectrometry. To our knowledge, this is the first report on the metabolites of MBDB-CHMICA in human urine.

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Authors and Affiliations

  1. Bureau of Forensic-Medical Expertise’s, Forensic-Chemical Division, Shhepkina Str. 61/2, Build. 8, Moscow, Russia

    Andrej Grigoryev

  2. Department of Pharmacology and Therapeutics, Trinity College, School of Medicine, Dublin 8, Ireland

    Pierce Kavanagh

  3. Bureau of Forensic-Medical Expertise’s, Forensic-Chemical Division, Glazkova Str. 2, Salekhard, Russia

    Alexandr Pechnikov

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  1. Andrej Grigoryev
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  2. Pierce Kavanagh
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Correspondence to Andrej Grigoryev.

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Grigoryev, A., Kavanagh, P. & Pechnikov, A. Human urinary metabolite pattern of a new synthetic cannabimimetic, methyl 2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate. Forensic Toxicol 34, 316–328 (2016). https://doi.org/10.1007/s11419-016-0319-8

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