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Forensic Toxicology

, Volume 34, Issue 2, pp 316–328 | Cite as

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

  • Andrej Grigoryev
  • Pierce Kavanagh
  • Alexandr Pechnikov
Original Article

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.

Keywords

Synthetic cannabinoid MDMB-CHMICA Human urine Metabolites GC–MS LC–QTOF LC–MSn 

Notes

Compliance with ethical standards

Conflict of interest

There are no financial or other relations that could lead to a conflict of interest.

Statement of human rights

All procedures performed in studies involving human participants were in accordance with the ethical standards of the institutional and/or national research committee and with the 1964 Helsinki declaration and its later amendments or comparable ethical standards.

Informed consent

For this type of study formal consent is not required.

Supplementary material

11419_2016_319_MOESM1_ESM.pdf (114 kb)
Supplementary material 1 (PDF 114 kb)

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Copyright information

© Japanese Association of Forensic Toxicology and Springer Japan 2016

Authors and Affiliations

  • Andrej Grigoryev
    • 1
  • Pierce Kavanagh
    • 2
  • Alexandr Pechnikov
    • 3
  1. 1.Bureau of Forensic-Medical Expertise’s, Forensic-Chemical DivisionMoscowRussia
  2. 2.Department of Pharmacology and TherapeuticsTrinity College, School of MedicineDublin 8Ireland
  3. 3.Bureau of Forensic-Medical Expertise’s, Forensic-Chemical DivisionSalekhardRussia

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