New designer drug α‐pyrrolidinovalerophenone (PVP): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques
- 24 February 2009
- journal article
- research article
- Published by Wiley in Journal of Mass Spectrometry
- Vol. 44 (6), 952-964
- https://doi.org/10.1002/jms.1571
Abstract
The aim of the present study was to identify the metabolites of the new designer drug α‐pyrrolidinovalerophenone (PVP) in rat urine using GC/MS techniques. Eleven metabolites of PVP could be identified suggesting the following metabolic steps: hydroxylation of the side chain followed by dehydrogenation to the corresponding ketone; hydroxylation of the 2″‐position of the pyrrolidine ring followed by dehydrogenation to the corresponding lactam or followed by ring opening to the respective aliphatic aldehyde and further oxidation to the respective carboxylic acid; degradation of the pyrrolidine ring to the corresponding primary amine; and hydroxylation of the phenyl ring, most probably in the 4′‐position. The authors' screening procedure for pyrrolidinophenones allowed the detection of PVP metabolites after application of a dose corresponding to a presumed user's dose. In addition, the involvement of nine different human cytochrome P450 (CYP) isoenzymes in the side chain hydroxylation of PVP was investigated and CYP 2B6, 2C19, 2D6, and 3A4 were found to catalyze this reaction. Copyright © 2009 John Wiley & Sons, Ltd.Keywords
This publication has 36 references indexed in Scilit:
- Biotechnological synthesis of drug metabolites using human cytochrome P450 2D6 heterologously expressed in fission yeast exemplified for the designer drug metabolite 4′-hydroxymethyl-α-pyrrolidinobutyrophenoneBiochemical Pharmacology, 2007
- Studies on the metabolism and toxicological detection of the designer drug 2,5‐dimethoxy‐4‐methyl‐β‐ phenethylamine (2C‐D) in rat urine using gas chromatographic/mass spectrometric techniquesJournal of Mass Spectrometry, 2006
- 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) Analogues: A Promising Class of Monoamine Uptake InhibitorsJournal of Medicinal Chemistry, 2006
- Studies on the metabolism and toxicological detection of the new designer drug 4′-methyl-α-pyrrolidinobutyrophenone (MPBP) in rat urine using gas chromatography–mass spectrometryJournal of Chromatography B, 2005
- New designer drug, 2,5‐dimethoxy‐4‐propylthio‐β‐phenethylamine (2C‐T‐7): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometryJournal of Mass Spectrometry, 2005
- Metabolism of the new designer drug α-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4′-methyl-α-pyrrolidinopropiophenone (MPPP) studied in rat urine using gas chromatography-mass spectrometryJournal of Chromatography B, 2003
- Validated assay for quantification of oxcarbazepine and its active dihydro metabolite 10‐hydroxycarbazepine in plasma by atmospheric pressure chemical ionization liquid chromatography/mass spectrometryJournal of Mass Spectrometry, 2002
- Biotransformation of PhencyclidineDrug Metabolism Reviews, 1985
- Metabolism of pyrovalerone hydrochlorideJournal of Medicinal Chemistry, 1970
- DIAZOHYDROCARBONSCanadian Journal of Research, 1950