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

Anal Bioanal Chem. 2015 Aug;407(21):6301-15. doi: 10.1007/s00216-015-8612-7. Epub 2015 Apr 19.

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-HRMS(2)), and (1)H and (13)C 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.Graphical Abstract.

MeSH terms

  • Alkylation
  • Cannabinoids / chemistry*
  • Carboxylic Acids / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Indazoles / chemistry*
  • Proton Magnetic Resonance Spectroscopy

Substances

  • Cannabinoids
  • Carboxylic Acids
  • Indazoles