Studies on the pyrrolinone metabolites derived from the tobacco alkaloid 1-methyl-2-(3-pyridinyl)pyrrole (beta-nicotyrine)

Chem Res Toxicol. 1999 Jun;12(6):508-12. doi: 10.1021/tx990019j.

Abstract

Previous studies have established that the tobacco alkaloid 1-methyl-2-(3-pyridyl)pyrrole (beta-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-beta-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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Free Radicals
  • Insecticides / metabolism*
  • Oxidation-Reduction
  • Plants, Toxic*
  • Pyridines / metabolism*
  • Pyrroles / metabolism*
  • Rabbits
  • Tobacco / metabolism*

Substances

  • Free Radicals
  • Insecticides
  • Pyridines
  • Pyrroles
  • alpha-nicotyrine