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 spectrometry

• Published in: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences Analytical technologies in the biomedical and life sciences, 2003-11, Vol.796 (2), p.253-266
• Main Authors: Springer, Dietmar, Fritschi, Giselher, Maurer, Hans H.
• Format: Article
• Language: English
• Subjects: 4′-Methyl-α-pyrrolidinopropiophenone; Analysis; Animals; Biological and medical sciences; Designer Drugs - metabolism; Designer Drugs - toxicity; Gas Chromatography-Mass Spectrometry - methods; General pharmacology; Male; Medical sciences; Pharmacology. Drug treatments; Propiophenones - toxicity; Propiophenones - urine; Pyrroles - toxicity; Pyrroles - urine; Pyrrolidines - toxicity; Pyrrolidines - urine; Rats; Rats, Wistar; α-Pyrrolidinopropiophenone
• ISSN: 1570-0232; 1873-376X
• DOI: 10.1016/j.jchromb.2003.07.008

R,S-α-pyrrolidinopropiophenone (PPP) is a new designer drug with assumed amphetamine-like effects which has appeared on the illicit drug market. The aim of this study was to identify the PPP metabolites using solid-phase extraction, ethylation or acetylation as well as to develop a toxicological detection procedure in urine using solid-phase extraction, trimethylsilylation and gas chromatography–mass spectrometry (GC–MS). Analysis of urine samples of rats treated with PPP revealed that PPP was extensively metabolized by hydroxylation of the pyrrolidine ring with subsequent dehydrogenation to the corresponding lactam, hydroxylation of the aromatic ring in position 4′ or double dealkylation of the pyrrolidine ring to the corresponding primary amine (cathinone) partly followed by reduction of the keto group to the corresponding secondary alcohol (norephedrines). As cathinone and the norephedrine diastereomers are also formed after intake of other drugs of abuse or medicaments, special attention must be paid to the detection of the unequivocal metabolite 2″-oxo-PPP as an unambiguous proof for the intake of PPP. The hydroxy groups were found to be partly conjugated. Based on these data, PPP could be detected in urine via its metabolites by full-scan GC–MS using mass chromatography for screening and library search for identification by comparison of the spectra with reference spectra. The same toxicological detection procedure can be applied to other designer drugs of the pyrrolidinophenone type, like MOPPP, MDPPP, MPHP, and MPPP. The detection of the latter will also be presented here.