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Analytical and Bioanalytical Chemistry

, Volume 407, Issue 21, pp 6301–6315 | Cite as

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

  • Vadim Shevyrin
  • Vladimir Melkozerov
  • Alexander Nevero
  • Oleg Eltsov
  • Yuri Shafran
  • Yuri Morzherin
  • Albert T. Lebedev
Paper in Forefront
Part of the following topical collections:
  1. High-Resolution Mass Spectrometry in Food and Environmental Analysis

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.

Graphical Abstract

Keywords

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

Supplementary material

216_2015_8612_MOESM1_ESM.pdf (3.2 mb)
ESM 1 (PDF 3.24 mb)

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Copyright information

© Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  • Vadim Shevyrin
    • 1
  • Vladimir Melkozerov
    • 2
  • Alexander Nevero
    • 3
  • Oleg Eltsov
    • 1
  • Yuri Shafran
    • 1
    • 4
  • Yuri Morzherin
    • 1
  • Albert T. Lebedev
    • 5
  1. 1.Institute of Chemistry and TechnologyUral Federal UniversityEkaterinburgRussian Federation
  2. 2.Expert and Criminalistic Center, Main Agency of the Ministry of the Interior of the Russian Federation, Sverdlovsk Region BranchEkaterinburgRussian Federation
  3. 3.State Committee of Forensic Expertise of Republic of BelarusMinskBelarus
  4. 4.TOSLab. Ltd.MoscowRussian Federation
  5. 5.Organic Chemistry DepartmentLomonosov Moscow State UniversityMoscowRussian Federation

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