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Forensic Toxicology
Published in: Forensic Toxicology 2/2016

01-07-2016 | Original Article

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

Authors: Andrej Grigoryev, Pierce Kavanagh, Alexandr Pechnikov

Published in: Forensic Toxicology | Issue 2/2016

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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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Metadata
Title
Human urinary metabolite pattern of a new synthetic cannabimimetic, methyl 2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate
Authors
Andrej Grigoryev
Pierce Kavanagh
Alexandr Pechnikov
Publication date
01-07-2016
Publisher
Springer Japan
Published in
Forensic Toxicology / Issue 2/2016
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-016-0319-8

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