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Alternate Routes In The Metabolic Degradation Of The Pyrrolidine Ring Of Nicotine



Alternate Routes In The Metabolic Degradation Of The Pyrrolidine Ring Of Nicotine



Journal of Biological Chemistry 239: 3990-3996



An extension of previous studies on the metabolism of 2 intermediates in the metabolism of nicotine, ( - )-cotinine and ( - )-demethylcotinine, has permitted the construction of a summary scheme for mammalian metabolism of nicotine. In both the rat and dog, ( - )-demethylcotinine undergoes degradation to gamma-(3-pyridyl)-gamma-oxobutyric acid and gamma-(3-pyridyl)-gamma-hydroxybutyric acid. The keto acid was identified after conversion to the methyl ester while the hydroxy acid was identified after conversion to the picrate of the lactone form. The pattern of excretion of urinary pyridyl acids after administration of ( - )-demethylcotinine is similar to that observed after administration of ( - )-cotinine. The administration of ( - )-cotinine to man led to the urinary excretion of 3-pyridylacetic acid, which was chemically identified for the first time as a metabolite of ( - )-cotinine in this species.

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Accession: 029980209

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PMID: 14257634


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