+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Studies on the degradation of the pyrrolidine ring of -nicotine in vivo. Formation of gamma- -gamma-oxobutyric acid



Studies on the degradation of the pyrrolidine ring of -nicotine in vivo. Formation of gamma- -gamma-oxobutyric acid



Jour Biol Chem 238(5): 1807-1812



(-)-Cotinine, a metabolite of (-)-nicotine, is metabolized in the rat and dog to gamma-(3-pyridyl)-gamma-oxobutyric acid. This keto acid was isolated from the urine of both species after conversion to the methyl ester. Identification was confirmed by a comparison with authentic samples of the picric acid and 5-nitrobarbituric acid salts of the methyl ester. After administration of gamma-(3-pyridyl)-gamma-(-)-cotinine, the rat excreted gamma-(3-pyridyl)-gamma-oxobutyric acid. The foregoing, associated data, and early experiments of Knoop with gamma-phenyl -gamma-oxobutyric acid is an intermediate in the metabolism of (-)-nicotine to 3-pyridylacetic acid.

Please choose payment method:






(PDF emailed within 1 workday: $29.90)

Accession: 025575742

Download citation: RISBibTeXText


Related references

Studies on the degradation of the pyrrolidine ring of (--)-nicotine in vivo. Formation of gamma-(3-pyridyl)-gamma-oxobutyric acid. Journal of Biological Chemistry 238: 1807-1812, 1963

Studies on nicotine metabolism: The formation of gamma- -gamma-methylaminobutyric acid. FED PROC 19(1 Pt 1): 30, 1960

The metabolic formation of gamma- -gamma-hydroxybutyric acid and its possible intermediary role in the mammalian metabolism of nicotine. J Biol Chem 239(11): 3981-3989, 1964

The Metabolic Formation of Gamma-(3-Pyridyl)-Gamma-Hydroxybutyric Acid and its Possible Intermediary Role in the Mammalian Metabolism of Nicotine. Journal of Biological Chemistry 239: 3981-3989, 1964

In vivo conversion of gamma-aminobutyric acid and 1,4-butanediol to gamma-hydroxybutyric acid in rat brain. Studies using stable isotopes. Biochemical Pharmacology 38(24): 4375-4380, 1989

Analytical studies on degradation mechanism of herbicide 4-chlorophenoxyacetic acid in water by gamma/H2O2 and gamma/ozone processes. Environmental Technology 37(19): 2494-2507, 2016

Alternate Routes In The Metabolic Degradation Of The Pyrrolidine Ring Of Nicotine. Journal of Biological Chemistry 239: 3990-3996, 1964

The biochemorphology of nicotine; observations on the progressive degradation of the pyrrolidine ring. Journal of Pharmacology and Experimental Therapeutics 88(1): 82-86, 1946

The biochemorphology of nicotine. I. Observations on the effect of progressive degradation of the pyrrolidine ring. Jour Pharmacol And Exptl Therap 88(1): 82-86, 1946

Formation of gamma aminobutyric acid in brain of mice treated with L-glutamic acid gamma-hydrazide and pyridoxal phosphate-gamma-glutamyl hydrazone. Proc Soc Exp Biol Med 126(1): 218-221, 1967

Formation of gamma-aminobutyric acid (GABA) in brain of mice treated with L-glutamic acid-gamma-hydrazide and pyridoxal phosphate-gamma-glutamyl hydrazone. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine 126(1): 218-221, 1967

Asymmetric synthesis of gamma gamma dialkyl gamma aminobutyric acid analogues and 2 2 disubstituted pyrrolidines control of stereochemistry in aminal ring opening by varying the extent of allylic 1 3 strain. Journal of the American Chemical Society 113(26): 9858-9859, 1991

Metabolism of 3-(p-chlorophenyl)pyrrolidine. Structural effects in conversion of a prototype gamma-aminobutyric acid prodrug to lactam and gamma-aminobutyric acid type metabolites. Journal of Medicinal Chemistry 32(6): 1340-1348, 1989

The action of gamma vinyl gamma amino butyric acid and gamma acetylenic gamma amino butyric acid on the resting and stimulated release of gamma amino butyric acid in vivo. Brain Research 191(2): 471-482, 1980

The effect of 4 amino hex 5 ynoic acid gamma acetylenic gamma amino butyric acid ethynyl a catalytic inhibitor of gamma amino butyric acid trans aminase ec 2.6.1.19 on brain gamma amino butyric acid metabolism in vivo. Journal of Neurochemistry 28(4): 717-723, 1977