122745-79-3Relevant academic research and scientific papers
Studies on the pyrrolinone metabolites derived from the tobacco alkaloid 1-methyl-2-(3-pyridinyl)pyrrole (β-nicotyrine)
Liu, Xin,Zang, Lunyi,Van Der Schyf, Cornells J.,Igarashi, Kazuo,Castagnoli, Kay,Castagnoli Jr., Neal
, p. 508 - 512 (1999)
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.
