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

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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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Authors and Affiliations

  1. Institute of Chemistry and Technology, Ural Federal University, 19 Mira Str., 620002, Ekaterinburg, Russian Federation

    Vadim Shevyrin, Oleg Eltsov, Yuri Shafran & Yuri Morzherin

  2. Expert and Criminalistic Center, Main Agency of the Ministry of the Interior of the Russian Federation, Sverdlovsk Region Branch, 17 Lenina Avenue, 620014, Ekaterinburg, Russian Federation

    Vladimir Melkozerov

  3. State Committee of Forensic Expertise of Republic of Belarus, 43 Kalvariyskaya Str., 220073, Minsk, Belarus

    Alexander Nevero

  4. TOSLab. Ltd., Bldg. 1, 5 Initsiativnaia Str., 121357, Moscow, Russian Federation

    Yuri Shafran

  5. Organic Chemistry Department, Lomonosov Moscow State University, Leninskie Gory 1/3, 119991, Moscow, Russian Federation

    Albert T. Lebedev

Authors
  1. Vadim Shevyrin
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  2. Vladimir Melkozerov
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  3. Alexander Nevero
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  4. Oleg Eltsov
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  5. Yuri Shafran
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  6. Yuri Morzherin
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  7. Albert T. Lebedev
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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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  • DOI: https://doi.org/10.1007/s00216-015-8612-7

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