title: Studies on the metabolism and detectability of the designer drug β-naphyrone in rat urine using GC-MS and LC-HR-MS/MS.
abstract: Naphyrone (1-naphthalen-2-yl-2-pyrrolidin-1-yl-pentan-1-one; naphthylpyrovalerone, β-naphyrone) is a cathinone designer drug and was marketed as replacement for the synthetic cathinone derivative mephedrone. Meanwhile, naphyrone is also classified as a controlled drug in several countries. Therefore, the aim of this study was to identify the metabolites of naphyrone in rat urine using gas chromatography-mass spectrometry techniques and to show its detectability in urine samples. The following metabolic steps could be detected in rat urine: oxidation of the pyrrolidine ring to the corresponding lactam, hydroxylation of the propyl side chain and the naphthyl ring, degradation to the primary amines after opening of the pyrrolidine ring, and combinations of these steps. Assuming similar kinetics, an intake of naphyrone should be detectable in human urine mainly via its metabolites.
authors.affiliation: Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical, Pharmacology and Toxicology, Saarland University, D-66421, Homburg, Saar, Germany. markus.meyer@uks.eu
authors.forename: Markus R
authors.initials: MR
authors.lastname: Meyer
authors.forename: Denise
authors.initials: D
authors.lastname: Prosser
authors.forename: Hans H
authors.initials: HH
authors.lastname: Maurer
mesh_terms: D000818:Animals; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D015198:Designer Drugs / Q000032:analysis* / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D013287:Illicit Drugs / Q000378:metabolism / Q000652:urine; D008297:Male; D010084:Oxidation-Reduction; D010422:Pentanones / Q000378:metabolism* / Q000652:urine*; D011759:Pyrrolidines / Q000378:metabolism* / Q000652:urine*; D051381:Rats; D017208:Rats, Wistar; D053719:Tandem Mass Spectrometry / Q000379:methods
chemical_list: C509270:1-naphthalen-2-yl-2-pyrrolidin-1-ylpentan-1-one; D015198:Designer Drugs; D013287:Illicit Drugs; D010422:Pentanones; D011759:Pyrrolidines; C400322:cytochrome P-450 CYP2C subfamily; D003577:Cytochrome P-450 Enzyme System