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01.07.2015 | Original Article

Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans

verfasst von: Noriaki Shima, Hidenao Kakehashi, Shuntaro Matsuta, Hiroe Kamata, Shihoko Nakano, Keiko Sasaki, Tooru Kamata, Hiroshi Nishioka, Kei Zaitsu, Takako Sato, Akihiro Miki, Munehiro Katagi, Hitoshi Tsuchihashi

Erschienen in: Forensic Toxicology | Ausgabe 2/2015

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Abstract

1-Phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) and 16 metabolites, including diastereomers and conjugates, were identified or tentatively detected in human urine by gas chromatography–mass spectrometry and liquid chromatography–high-resolution tandem mass spectrometry. These urinary metabolites indicated that the metabolic pathways of PV9 include: (1) the reduction of ketone groups to their corresponding alcohols; (2) oxidation of the pyrrolidine ring to the corresponding pyrrolidone; (3) aliphatic oxidation of the terminal carbon atom to the corresponding carboxylate form, possibly through an alcohol intermediate (not detected); and (4) hydroxylation at the penultimate carbon atom to the corresponding alcohols followed by further oxidation to ketones, and combinations of these steps. In addition, results from the quantitative analyses of five phase-I metabolites using newly synthesized authentic standards suggested that the main metabolic pathway includes the aliphatic oxidation of terminal and/or penultimate carbons. Human metabolism of PV9 differed significantly from those of α-pyrrolidinovalerophenone and α-pyrrolidinobutiophenone, suggesting that the main metabolic pathways of α-pyrrolidinophenones significantly change depending on the alkyl chain length of the parent molecule.

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Titel: Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans
verfasst von: Noriaki Shima
Hidenao Kakehashi
Shuntaro Matsuta
Hiroe Kamata
Shihoko Nakano
Keiko Sasaki
Tooru Kamata
Hiroshi Nishioka
Kei Zaitsu
Takako Sato
Akihiro Miki
Munehiro Katagi
Hitoshi Tsuchihashi
Publikationsdatum: 01.07.2015
Verlag: Springer Japan
Erschienen in: Forensic Toxicology / Ausgabe 2/2015
Print ISSN: 1860-8965
Elektronische ISSN: 1860-8973
DOI: https://doi.org/10.1007/s11419-015-0274-9

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Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans

Abstract

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Abstract

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