Tobacco product use results in exposure to a diverse array of compounds including over 60 carcinogens, the addictive compound nicotine and less well studied compounds such as �-nicotyrine.  �-Nicotyrine differs from nicotine only in that the pyrrolidine ring has been aromatized by the loss of four hydrogen atoms. Pharmaceutically slowing nicotine metabolism in smokers has been found to help them smoke less and possibly quit. CYP2A6 is the primary catalyst of nicotine metabolism and here we present evidence that �-nicotyrine is a product of this reaction. We have recently confirmed that �-nicotyrine is a mechanism-based inactivator of CYP2A6. Dehydrocotinine, which is likely formed by way of an expoxide, was identified as a metabolite of �-nicotyrine. The epoxide may contribute to the �-nicotyrine mediated inactivation of CYP2A6 that we have reported.

Cytochrome P450 2A6 mediated metabolism of β-nicotyrine

244th National Meeting (2012)

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