title: Biotransformation and detectability of the designer drug 2,5-dimethoxy-4-propylphenethylamine (2C-P) studied in urine by GC-MS, LC-MS(n), and LC-high-resolution-MS(n).
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-MS(n) approach.
authors.affiliation: Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, Saarland University, 66421, Homburg, Saar, Germany.
authors.forename: Carina S D
authors.initials: CS
authors.lastname: Wink
authors.forename: Markus R
authors.initials: MR
authors.lastname: Meyer
authors.forename: Tina
authors.initials: T
authors.lastname: Braun
authors.forename: Alain
authors.initials: A
authors.lastname: Turcant
authors.forename: Hans H
authors.initials: HH
authors.lastname: Maurer
mesh_terms: D000107:Acetylation; D000818:Animals; D002853:Chromatography, Liquid / Q000295:instrumentation / Q000379:methods; D015198:Designer Drugs / Q000378:metabolism* / Q000493:pharmacokinetics; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D006801:Humans; D008297:Male; D013058:Mass Spectrometry / Q000295:instrumentation / Q000379:methods*; D010627:Phenethylamines / Q000378:metabolism* / Q000493:pharmacokinetics / Q000652:urine*; D017208:Rats, Wistar
chemical_list: C487778:2,5-dimethoxy-4-n-propylthiophenethylamine; D015198:Designer Drugs; D010627:Phenethylamines