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Biotransformation and detectability of the designer drug 2,5-dimethoxy-4-propylphenethylamine (2C-P) studied in urine by GC-MS, LC-MSn, and LC-high-resolution-MSn

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Abstract

2,5-Dimethoxy-4-propylphenethylamine (2C-P) is a hallucinogenic designer drug of the phenethylamine class, the so-called 2Cs, named according to the ethyl spacer between the nitrogen and the aromatic ring. The aims of the present work were to identify the phases I and II metabolites of 2C-P. In addition, the detectability of 2C-P and its metabolites in urine as proof of an intake in clinical or forensic cases was tested. According to the identified metabolites, the following pathways were proposed: N-acetylation; deamination followed by reduction to the corresponding alcohol and oxidation to carbonic acid; mono- and bis-hydroxylation at different positions; mono- and bis-O-demethylation, followed by glucuronidation, sulfation, or both; and combination of these steps. Proof of an intake of a common user’s dose of 2C-P was possible by both standard urine screening approaches, the GC-MS as well as the LC-MSn approach.

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Acknowledgments

The authors like to thank Achim Caspar, Andreas Helfer, Golo M. J. Meyer, Julian Michely, Carsten Schröder, Gabriele Ulrich, and Armin A. Weber for their support.

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Authors and Affiliations

  1. Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, Saarland University, 66421, Homburg, Saar, Germany

    Carina S. D. Wink, Markus R. Meyer, Tina Braun & Hans H. Maurer

  2. Laboratoire de Pharmacologie-Toxicologie, Centre Hospitalier Universitaire, Angers, France

    Alain Turcant

Authors
  1. Carina S. D. Wink
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  2. Markus R. Meyer
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  3. Tina Braun
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  4. Alain Turcant
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  5. Hans H. Maurer
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Correspondence to Hans H. Maurer.

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Published in the topical collection celebrating ABCs 13th Anniversary.

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Wink, C.S.D., Meyer, M.R., Braun, T. et al. Biotransformation and detectability of the designer drug 2,5-dimethoxy-4-propylphenethylamine (2C-P) studied in urine by GC-MS, LC-MSn, and LC-high-resolution-MSn . Anal Bioanal Chem 407, 831–843 (2015). https://doi.org/10.1007/s00216-014-8083-2

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  • DOI: https://doi.org/10.1007/s00216-014-8083-2

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