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Metabolites of synthetic cannabinoids in hair—proof of consumption or false friends for interpretation?

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Abstract

The detection of drug metabolites in hair is widely accepted as a proof for systemic uptake of the drug, unless the metabolites can be formed as artefacts. However, regarding synthetic cannabinoids, not much is known about mechanisms of incorporation into hair. For a correct interpretation concerning hair findings of these compounds and their metabolites, it is necessary to identify the different routes of incorporation and to assess their contribution to analytical findings. This study presents the results of the LC-ESI-MS/MS analysis of an authentic hair sample taken from a patient with a known history of heavy consumption of synthetic cannabinoids. In the authentic hair sample, 5F-PB-22 and AB-CHMINACA as well as their main metabolites 5F-PB-22 3-carboxyindole, PB-22 5-OH-pentyl, and AB-CHMINACA valine were detected in all segments, comprising segments grown in a time period where the substances had not been distributed on the ‘legal high’ market. To enable interpretation of the results regarding the distribution of the detected analytes along the hair shaft, the stability of 5F-PB-22 and AB-CHMINACA in hair matrix and under thermal stress was assessed. The stability tests revealed that the three ‘metabolites’ are also formed in externally contaminated hair after storage of the samples under different conditions. In addition, 5F-PB-22 3-carboxyindole and AB-CHMINACA valine were identified as degradation products in smoke condensate. Therefore, interpretation of ‘metabolite’ findings of compounds comprising chemically labile amide/ester bonds or 5-fluoro-pentyl side chains should be carried out with utmost care, taking into account the different mechanisms of formation and incorporation into hair.

Degradation processes leading to artefacts identical with main metabolites of synthetic cannabinoids

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Acknowledgments

The authors would like to thank Nadine Schiesel for her commitment in this project and her support in the laboratory work.

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Authors and Affiliations

  1. Institute of Forensic Medicine, Forensic Toxicology, Medical Center—University of Freiburg, Albertstraße 9, 79104, Freiburg, Germany

    Florian Franz, Verena Angerer, Volker Auwärter & Bjoern Moosmann

  2. Hermann Staudinger Graduate School, University of Freiburg, Hebelstraße 27, 79104, Freiburg, Germany

    Florian Franz & Verena Angerer

  3. Poison Information Center, Center for Pediatrics and Adolescent Medicine, Medical Center—University of Freiburg, Mathildenstraße 1, 79106, Freiburg, Germany

    Maren Hermanns-Clausen

Authors
  1. Florian Franz
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  2. Verena Angerer
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  3. Maren Hermanns-Clausen
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  4. Volker Auwärter
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  5. Bjoern Moosmann
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Corresponding author

Correspondence to Bjoern Moosmann.

Ethics declarations

The samples were obtained in the scope of the study ‘Spice II plus: New drugs of abuse: acute intoxication by synthetic cannabinoids and by new stimulants’ which was approved by the Ethics Committee of the University of Freiburg, Germany (EK-Freiburg 235/13 & 235/13_130683). Informed consent was given by all study participants. All further experiments in this study comply with current German laws.

Funding

This publication has been produced with the financial support of the ‘Prevention of and Fight against Crime’ program of the European Commission (JUST/2013/ISEC/DRUGS/AG/6421).

Conflict of interest

The authors declare that they have no conflict of interest.

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Franz, F., Angerer, V., Hermanns-Clausen, M. et al. Metabolites of synthetic cannabinoids in hair—proof of consumption or false friends for interpretation?. Anal Bioanal Chem 408, 3445–3452 (2016). https://doi.org/10.1007/s00216-016-9422-2

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  • DOI: https://doi.org/10.1007/s00216-016-9422-2

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