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Studies on the Pyrrolinone Metabolites Derived from the Tobacco Alkaloid 1-Methyl-2-(3-pyridinyl)pyrrole (β-Nicotyrine)

Previous studies have established that the tobacco alkaloid 1-methyl-2-(3-pyridyl)pyrrole (β-nicotyrine) is biotransformed by rabbit lung and liver microsomal preparations to an equilibrium mixture of the corresponding 3- and 4-pyrrolin-2-ones. Autoxidation of these pyrrolin-2-ones generates the che...

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Bibliographic Details
Published in:Chemical research in toxicology 1999-06, Vol.12 (6), p.508-512
Main Authors: Liu, Xin, Zang, Lunyi, Van der Schyf, Cornelis J, Igarashi, Kazuo, Castagnoli, Kay, Castagnoli, Neal
Format: Article
Language:English
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Summary:Previous studies have established that the tobacco alkaloid 1-methyl-2-(3-pyridyl)pyrrole (β-nicotyrine) is biotransformed by rabbit lung and liver microsomal preparations to an equilibrium mixture of the corresponding 3- and 4-pyrrolin-2-ones. Autoxidation of these pyrrolin-2-ones generates the chemically stable 5-hydroxy-5-(3-pyridinyl)-3-pyrrolin-2-one. This paper summarizes efforts to document more completely the pathway leading to this hydroxypyrrolinone. Chemical and spectroscopic evidence implicates the 2-hydroxy-1-methyl-5-(3-pyridinyl)pyrrole (2-hydroxy-β-nicotyrine) as the key intermediate in this reaction pathway. Of potential toxicological interest is the detection of radical species derived from the autoxidation of this compound.
ISSN:0893-228X
1520-5010
DOI:10.1021/tx990019j