Mammalian Degradation of (-)-Nicotine to 3-Pyridylacetic Acid and Other Compounds. ∗

Abstract

Summary

1. The pattern of urinary excretion of C¹⁴ in the dog following intravenous administration of (-)-nicotine-C¹⁴ has been examined chromatographically by improved procedures. 2. The fractionated urine showed C¹⁴ activity corresponding chromatographically to the known metabolites: cotinine, γ- (3-pyridyl)-γ-methylaminobutyric acid, desmethylcotinine-hydroxycotinine, and γ-(3-pyridyl)-β-oxo-N-methylbutyramide. 3. Among many unidentified radioactive components, the urine contained material corresponding chromatographically to 3-pyridyl-acetic acid. 4. Following oral administration of (-)-cotinine to the dog. 3-pyridylacetic: acid was isolated from urine and characterized by analysis, melting point, mixed melting point and as its picric acid salt. 5. A precursor of 3-pyridylacetic acid is on formal grounds γ-(3-pyridyl)-β-oxobutyric acid, derivable from the known metabolite γ-(3-pyridyl)-β-oxo-N-methylbutyramide.