Determination of the Structures of Free and Glucuronidated Metabolites of α-Pyrrolidinovalerophenone in Human Urine by Liquid Chromatography–Mass Spectrometry with Accurate Mass Measurement
- Authors: Zaikina O.L.1, Shilov V.V.2, Lodyagin A.N.3, Glushkov S.I.3, Grigoryev A.M.4
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Affiliations:
- Leningrad Regional Narcology Dispensary
- Mechnikov North-Western State Medical University
- Dzhanelidze Research Institute of Emergency Medicine
- Bureau of Forensic Medicine
- Issue: Vol 74, No 5 (2019)
- Pages: 489-504
- Section: Articles
- URL: https://journals.rcsi.science/1061-9348/article/view/183214
- DOI: https://doi.org/10.1134/S1061934819020138
- ID: 183214
Cite item
Abstract
The central nervous system stimulant, designer drug α-pyrrolidinovalerophenone (PVP), a member of a large group of cathinone derivatives, is highly popular among drug-dependent groups. α-Pyrrolidinovalerophenone is extensively metabolized and excreted in urine, accompanied by a significant number of metabolites. Using liquid chromatography–tandem mass spectrometry, we determined the structures of more than 60 suspected PVP metabolites present in human urine in both free and glucuronidated forms. Structural features of the metabolites were determined by interpreting high-resolution mass spectra and chromatographic retention in changing the acidity of the eluent. The compounds found are products of hydroxylation of propyl, pyrrole, and phenyl moieties, reduction of the carbonyl group to an alcohol one, carboxylation, the formation of keto groups, oxidative deamination, destruction of the pyrrole cycle to the primary amine, as well as combinations of these processes. Based on the results of measuring the relative heights of chromatographic peaks, an optimal set of metabolites is proposed for the subsequent routine screening of urine samples by liquid chromatography–mass spectrometry.
About the authors
O. L. Zaikina
Leningrad Regional Narcology Dispensary
Email: chrzond4250@yandex.ru
Russian Federation, Novoe Devyatkino, Leningradskaya oblast, 188661
V. V. Shilov
Mechnikov North-Western State Medical University
Email: chrzond4250@yandex.ru
Russian Federation, St. Petersburg, 195067
A. N. Lodyagin
Dzhanelidze Research Institute of Emergency Medicine
Email: chrzond4250@yandex.ru
Russian Federation, St. Petersburg, 192242
S. I. Glushkov
Dzhanelidze Research Institute of Emergency Medicine
Email: chrzond4250@yandex.ru
Russian Federation, St. Petersburg, 192242
A. M. Grigoryev
Bureau of Forensic Medicine
Author for correspondence.
Email: chrzond4250@yandex.ru
Russian Federation, Moscow, 111401