Metabolism of the newly encountered designer drug α-pyrrolidinovalerophenone in humans: identification and quantitation of urinary metabolites
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Urinary metabolites of α-pyrrolidinovalerophenone (α-PVP) in humans were investigated by analyzing urine specimens obtained from abusers. Unambiguous identification and accurate quantification of major metabolites were realized using gas chromatography–mass spectrometry and liquid chromatography-tandem mass spectrometry with newly synthesized authentic standards. Two major metabolic pathways were revealed: (1) the reduction of the β-keto moiety to 1-phenyl-2-(pyrrolidin-1-yl)pentan-1-ol (OH-α-PVP, diastereomers) partly followed by conjugation to its glucuronide, and (2) the oxidation at the 2″-position of the pyrrolidine ring to α-(2″-oxo-pyrrolidino)valerophenone (2″-oxo-α-PVP) via the putative intermediate α-(2″-hydroxypyrrolidino)valerophenone (2″-OH-α-PVP). Of the metabolites retaining the structural characteristics of the parent drug, OH-α-PVP was most abundant in most of the specimens examined.
Keywordsα-PVP metabolism Cathinone drug 1-Phenyl-2-(pyrrolidin-1-yl)pentan-1-ol (OH-α-PVP) (2″-Oxo-pyrrolidino)valerophenone (2″-oxo-α-PVP) LC–MS–MS Urine
The authors would like to thank Prof. Dr. Iwamura (Matsuyama University) for his valuable suggestions in synthesizing the standards.
Conflict of interest
There are no financial or other relations that could lead to a conflict of interest.
- 4.Meyer MR, Du P, Schuster F, Maurer HH (2010) Studies on the metabolism of the α-pyrrolidinophenone designer drug methylenedioxy-pyrovalerone (MDPV) in rat and human urine and human liver microsomes using GC–MS and LC-high resolution MS and its detectability in urine by GC–MS. J Mass Spectrom 45:1426–1442PubMedCrossRefGoogle Scholar
- 16.Shima N, Katagi M, Kamata H, Matsuta S, Nakanishi K, Zaitsu K, Kamata T, Nishioka H, Miki A, Tatsuno M, Sato T, Tsuchihashi H, Suzuki K (2013) Urinary excretion and metabolism of the newly encountered designer drug 3,4-dimethylmethcathinone in humans. Forensic Toxicol 31:101–112CrossRefGoogle Scholar
- 17.Meyer MR, Wilhelm J, Peters FT, Maurer HH (2010) Beta-keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry. Anal Bioanal Chem 397:1225–1233PubMedCrossRefGoogle Scholar