Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group

Abstract

Illicit new psychoactive substances (NPS) are a serious threat to health throughout the world. Such NPS do not usually pass preliminary pharmacological trials. In 2014, we identified a series of five new synthetic cannabinoids with an indazole-3-carboxamide structure bearing an N-1-methoxycarbonylalkyl group. The compounds have very high cannabimimetic activity which has caused mass severe intoxication and deaths. The compounds were identified by means of gas chromatography–mass spectrometry (GC–MS), including high-resolution mass spectrometry (GC–HRMS), ultra-high-performance liquid chromatography–high-resolution tandem mass spectrometry (UHPLC–HRMS2), and 1H and 13C nuclear magnetic resonance spectroscopy (NMR). The peculiarities of mass-spectral fragmentation of the compounds after electron ionization (EI) ionization and collision-induced dissociation (CID) were studied. The analytical characteristics reported for the compounds will enable their identification in a variety of materials seized from criminals.

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Correspondence to Albert T. Lebedev.

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Published in the topical collection High-Resolution Mass Spectrometry in Food and Environmental Analysis with guest editor Aldo Laganà.

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Shevyrin, V., Melkozerov, V., Nevero, A. et al. Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group. Anal Bioanal Chem 407, 6301–6315 (2015). https://doi.org/10.1007/s00216-015-8612-7

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Keywords

  • Synthetic cannabinoids
  • New psychoactive substances
  • Indazole-3-carboxamides
  • High-resolution mass spectrometry
  • Chromatography
  • NMR