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Elucidation of the Chemical Structure of a Gas Chromatographic Artifact of Synthetic Cannabinoid N-(1-Carbamoyl-2-Methylpropyl)-1-(Cyclohexylmethyl)-1H-Indazol-3Ccarboxamide by High-Resolution Mass Spectrometry

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Abstract

Synthetic cannabinoids are the most popular psychoactive compounds on the illegal market. In the gas chromatographic determination, some synthetic cannabinoids undergo chemical transformations because of their thermal interaction with the chromatographic system. This paper is devoted to the elucidation of the structure of a gas chromatographic artifact formed from synthetic cannabinoid N-(1-carbamoyl-2-methylpropyl)-1-(cyclohexylmethyl)-1H-indazol-3-carboxamide as a result of dehydration of its terminal carbamoyl moiety. The chemical structure of the artifact is determined by high-resolution mass spectrometry.

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References

  1. United Nation Office on Drugs and Crime (UNODC), World Drug Report 2016, New York, United Nations, 2016. http://www.unodc.org/doc/wdr2016/World_ drug_report_2016_web.pdf.

  2. Castaneto, M.S., Gorelick, D.A., Desrosiers, N.A., et al., Drug Alcohol Depend., 2014, vol. 144, p. 12.

    Article  CAS  Google Scholar 

  3. Shevyrin, V.A., Morzherin, Yu.Yu., Russ. Chem. Bull., 2015, vol. 64, no. 6, p. 1249.

    Article  CAS  Google Scholar 

  4. Shevyrin, V.A., Sinteticheskie kannabinoidy v kachestve novyhk psikhoaktivnykh soedinenii. Ustanovlenie structur, analiticheskie kharakteristiki, metody opredeleniya i identifikatsiya v ob”ektakh analiza narkoticheskikh sredstv (Synthetic cannabinoids as new psychoactive substances. Determination the structures, analytical char-acteristics, methods of detection and identification of objects in the analysis of drugs), Moscow: Pero, 2015, 608 p.

    Google Scholar 

  5. Uchiyama, N., Shimokawa, Y., Kawamura, M., et al., Forensic Toxicol., 2014, vol. 32, no. 2, p. 266.

    Article  CAS  Google Scholar 

  6. Buchler, I.P., Hayes, M.J., Hedge, S.G., et al., US Patent WO2009106980, 2009.

    Google Scholar 

  7. Shevyrin, V., Melkozerov, V., Nevero, A., et al., Forensic Sci. Int., 2013, vol. 226, nos. 1–3, p. 62.

    Article  CAS  Google Scholar 

  8. Tsujikawa, K., Yamamuro, T., Kuwayama, K., et al., Forensic Toxicol., 2014, vol. 32, no. 2, p. 201.

    Article  CAS  Google Scholar 

  9. AIPSIN AntiNarkotiki Information-Search System. http://aipsin.com/kb/aipsin/ips/drugs.html.

  10. Bhattacharyya, N.K., Jha, S., Jha, S., et al., Int. J. Chem. Appl., 2012, vol. 4, no. 4, p. 295.

    Google Scholar 

  11. Geng, H. and Huang, P.-Q., Tetrahedron, 2015, vol. 71, no. 23, p. 3795.

    Article  CAS  Google Scholar 

  12. Bose, D.S. and Jayalakshmi, B., Synthesis, 1999, no. 1, p. 64.

    Article  Google Scholar 

  13. Bhalerao, D.S., Mahajan, U.S., Chaudhari, K.H., et al., Org. Chem., 2007, vol. 72, no. 2, p. 662.

    Article  CAS  Google Scholar 

  14. Sueoka, S., Mitsudome, T., Mizugaki, T., et al., Chem. Commun., 2010, vol. 46, no. 43, p. 8243.

    Article  CAS  Google Scholar 

  15. Fatiadi, A.J., in The Chemistry of Triple-Bonded Functional Groups, Patai, S. and Rappoport, Z., Eds., Wiley, 1983, Suppl. C, Part 1, p. 1057.

  16. Shevyrin, V., Melkozerov, V., Nevero, A., et al., Anal. Bioanal. Chem., 2015, vol. 407, no. 21, p. 6301.

    Article  CAS  Google Scholar 

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Correspondence to Vadim A. Shevyrin.

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Original Russian Text © Vadim A. Shevyrin, 2016, published in Mass-spektrometriya, 2016, Vol. 13, No. 4, pp. 247–251.

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Shevyrin, V.A. Elucidation of the Chemical Structure of a Gas Chromatographic Artifact of Synthetic Cannabinoid N-(1-Carbamoyl-2-Methylpropyl)-1-(Cyclohexylmethyl)-1H-Indazol-3Ccarboxamide by High-Resolution Mass Spectrometry. J Anal Chem 72, 1340–1344 (2017). https://doi.org/10.1134/S1061934817130093

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  • DOI: https://doi.org/10.1134/S1061934817130093

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