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Highly sensitive screening and analytical characterization of synthetic cannabinoids in nine different herbal mixtures

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Abstract

The popularity of new psychoactive substances among drug users has become a public health concern worldwide. Among them, synthetic cannabinoids (SCs) represent the largest, most diversified and fastest growing group. Commonly known as ‘synthetic marijuana’ as an alternative to cannabis, these synthetic compounds are easily accessible via the internet and are sold as ‘herbal incenses’ under different brand names with no information about the chemical composition. In the present work, we aim to integrate gas chromatography-tandem mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) data as useful strategy for the identification and confirmation of synthetic cannabinoids present in nine seized herbal incenses. The analysis of all samples allowed the initial identification of 9 SCs, namely 5 napthoylindoles (JWH-018, JWH-073, JWH-122, JWH-210, MAM-2201), APINACA, XLR-11 and CP47,497-C8 and its enantiomer. JWH-018 was the most frequently detected synthetic compound (8 of 9 samples), while APINACA and XLR-11 were only identified in one herbal product. Other non-cannabinoid drugs, including oleamide, vitamin E and vitamin E acetate, have also been detected. Oleamide and vitamin E are two adulterants, frequently added to herbal products to mask the active ingredients or added as preservatives. However, to our knowledge, no analytical data about vitamin E acetate was reported in herbal products, being the first time that this compound is identified on this type of samples. The integration data obtained from the used analytical technologies proved to be useful, allowing the preliminary identification of the different SCs in the mixture. Furthermore, the examination of mass spectral fragment ions, as well as the results of both 1D and 2D NMR experiments, enabled the identification and confirmation of the molecular structure of SCs.

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Acknowledgments

The authors would like to thank LPC-PJ for their collaboration in providing seized herbal products.

Funding

This work was supported by FCT-Fundação para a Ciência e a Tecnologia through the CQM Base Fund (UIDB/00674/2020, and Programmatic Fund - UIDP/00674/2020), and the PhD fellowships SFRH/BD/117426/2016 and SFRH/BD/116895/2016 granted to Vera Alves and João Gonçalves respectively, and through Madeira 14-20 Program, project PROEQUIPRAM - Reforço do Investimento em Equipamentos e Infraestruturas Científicas na RAM (M1420-01-0145-FEDER-000008), and by ARDITI-Agência Regional para o Desenvolvimento da Investigação Tecnologia e Inovação, through the project M1420-01-0145-FEDER-000005 - Centro de Química da Madeira - CQM+ (Madeira 14–20 Program).

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Authors and Affiliations

  1. CQM - Centro de Química da Madeira, Universidade da Madeira, Campus Universitário da Penteada, 9020-105, Funchal, Portugal

    Vera L. Alves, João L. Gonçalves, Joselin Aguiar & José S. Câmara

  2. Laboratório de Polícia Científica da Polícia Judiciária, Novo edifício-sede da Polícia Judiciária, Rua Gomes Freire, 1169-007, Lisbon, Portugal

    Maria J. Caldeira

  3. Instituto Nacional de Medicina Legal e Ciências Forenses, I.P., Polo das Ciências de Saúde (Polo III), Azinhaga de Santa Comba, 3000-548, Coimbra, Portugal

    Helena M. Teixeira

  4. Faculdade de Medicina, Universidade de Coimbra, Azinhaga de Santa Comba, Celas, 3000-548, Coimbra, Portugal

    Helena M. Teixeira

  5. Faculdade de Ciências Exatas e da Engenharia, Universidade da Madeira, Campus da Penteada, 9020-105, Funchal, Portugal

    José S. Câmara

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  1. Vera L. Alves
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  4. Maria J. Caldeira
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Contributions

Vera Alves: Investigation, methodology, data curation, writing—original draft. João Gonçalves: Visualization, data curation, methodology. Joselin Aguiar: Investigation and methodology. Helena Teixeira: Conceptualization, supervision, review and editing. José S. Câmara: Supervision, resources, project administration, funding acquisition, supervision, review and editing.

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Correspondence to José S. Câmara.

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Alves, V.L., Gonçalves, J.L., Aguiar, J. et al. Highly sensitive screening and analytical characterization of synthetic cannabinoids in nine different herbal mixtures. Anal Bioanal Chem 413, 2257–2273 (2021). https://doi.org/10.1007/s00216-021-03199-6

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