Biotransformation and detectability of the designer drug 2,5-dimethoxy-4-propylphenethylamine studied in urine by GC-MS, [LC-MS.sup.n], and [LC-high-resolution-MS.sup.n]

• Published in: Analytical and bioanalytical chemistry 2015-01, p.831
• Main Authors: Wink, Carina S.D, Meyer, Markus R, Braun, Tina, Turcant, Alain, Maurer, Hans H
• Format: Article
• Language: English
• Subjects: Chemical properties; Composition; Gas chromatography; Hallucinogenic drugs; Identification and classification; Liquid chromatography; Mass spectrometry; Methods; Urine
• ISSN: 1618-2642
• DOI: 10.1007/S00216-014-8083-2

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 of2C-P was possible by both standard urine screening approaches, the GCMS as well as the [LC-MS.sup.n] approach. Keywords 2C-P * Phenethylamine derivatives * Metabolism * GC-MS * [LC-HR-MS.sup.n]