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Chemical Compound Review

CHEMBL434108     3-(1-nitrosopyrrolidin-2- yl)pyridine

Synonyms: AG-H-23670, CTK3E8244, LS-131869, LS-185119, AKOS006282074, ...
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Disease relevance of N-NITROSONORNICOTINE


High impact information on N-NITROSONORNICOTINE


Biological context of N-NITROSONORNICOTINE


Anatomical context of N-NITROSONORNICOTINE


Associations of N-NITROSONORNICOTINE with other chemical compounds




Analytical, diagnostic and therapeutic context of N-NITROSONORNICOTINE


  1. Evidence for cytochrome P450 2A6 and 3A4 as major catalysts for N'-nitrosonornicotine alpha-hydroxylation by human liver microsomes. Patten, C.J., Smith, T.J., Friesen, M.J., Tynes, R.E., Yang, C.S., Murphy, S.E. Carcinogenesis (1997) [Pubmed]
  2. Effect of N'-nitrosonornicotine (NNN) on murine palatal fusion in vitro. Saito, T., Cui, X.M., Yamamoto, T., Shiomi, N., Bringas, P., Shuler, C.F. Toxicology (2005) [Pubmed]
  3. Intranuclear rodlets in undifferentiated carcinomas of salivary glands in strain A mice in a study involving a tobacco specific nitrosamine, N-nitrosonornicotine. Hirota, N. Cancer Lett. (1979) [Pubmed]
  4. Kinetics of nornicotine and anabasine nitrosation in relation to N'-nitrosonornicotine occurrence in tobacco and to tobacco-induced cancer. Mirvish, S.S., Sams, J., Hecht, S.S. J. Natl. Cancer Inst. (1977) [Pubmed]
  5. DNA sequence context affects repair of the tobacco-specific adduct O(6)-[4-Oxo-4-(3-pyridyl)butyl]guanine by human O(6)-alkylguanine-DNA alkyltransferases. Mijal, R.S., Kanugula, S., Vu, C.C., Fang, Q., Pegg, A.E., Peterson, L.A. Cancer Res. (2006) [Pubmed]
  6. Biomarkers for human uptake and metabolic activation of tobacco-specific nitrosamines. Hecht, S.S., Carmella, S.G., Foiles, P.G., Murphy, S.E. Cancer Res. (1994) [Pubmed]
  7. O6-methylguanine is a critical determinant of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone tumorigenesis in A/J mouse lung. Peterson, L.A., Hecht, S.S. Cancer Res. (1991) [Pubmed]
  8. Comparative metabolism of N'-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by cultured F344 rat oral tissue and esophagus. Murphy, S.E., Heiblum, R., Trushin, N. Cancer Res. (1990) [Pubmed]
  9. Accumulation of 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone in alkaloid genotypes of burley tobacco during postharvest processing: comparisons with N'-nitrosonornicotine and probable nitrosamine precursors. Andersen, R.A., Kemp, T.R. Cancer Res. (1985) [Pubmed]
  10. Mutagenesis induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N-nitrosonornicotine in lacZ upper aerodigestive tissue and liver and inhibition by green tea. von Pressentin , M.M., Chen, M., Guttenplan, J.B. Carcinogenesis (2001) [Pubmed]
  11. Metabolism and pharmacokinetics of N'-nitrosonornicotine in the patas monkey. Upadhyaya, P., Zimmerman, C.L., Hecht, S.S. Drug Metab. Dispos. (2002) [Pubmed]
  12. Systemic genotoxic effects of tobacco-related nitrosamines following oral and inhalational administration to Sprague-Dawley rats. Pool-Zobel, B.L., Klein, R.G., Liegibel, U.M., Kuchenmeister, F., Weber, S., Schmezer, P. The Clinical investigator. (1992) [Pubmed]
  13. Assay for microsomal alpha-hydroxylation of N'-nitrosonornicotine and determination of the deuterium isotope effect for alpha-hydroxylation. Chen, C.H., Fung, P.T., Hecht, S.S. Cancer Res. (1979) [Pubmed]
  14. Induction of oral cavity tumors in F344 rats by tobacco-specific nitrosamines and snuff. Hecht, S.S., Rivenson, A., Braley, J., DiBello, J., Adams, J.D., Hoffmann, D. Cancer Res. (1986) [Pubmed]
  15. Formation of tissue-bound N'-nitrosonornicotine metabolites by the target tissues of Sprague-Dawley and Fisher rats. Brittebo, E.B., Tjälve, H. Carcinogenesis (1981) [Pubmed]
  16. Evidence for a high-affinity enzyme in rat esophageal microsomes which alpha-hydroxylates N'-nitrosonornicotine. Murphy, S.E., Spina, D.A. Carcinogenesis (1994) [Pubmed]
  17. Comparative carcinogenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N'-nitrosonornicotine in Syrian golden hamsters. Hoffmann, D., Castonguay, A., Rivenson, A., Hecht, S.S. Cancer Res. (1981) [Pubmed]
  18. Differential effect of chronic ethanol consumption on the carcinogenicity of N-nitrosopyrrolidine and N'-nitrosonornicotine in male Syrian golden hamsters. McCoy, G.D., Hecht, S.S., Katayama, S., Wynder, E.L. Cancer Res. (1981) [Pubmed]
  19. Effect of nicotine and N'-nitrosonornicotine on rat lung and trachea ornithine decarboxylase activity. Olson, J.W., Crooks, P.A. Carcinogenesis (1985) [Pubmed]
  20. Tobacco-specific nitrosamines and their pyridine-N-glucuronides in the urine of smokers and smokeless tobacco users. Stepanov, I., Hecht, S.S. Cancer Epidemiol. Biomarkers Prev. (2005) [Pubmed]
  21. Dose-response study of the carcinogenicity of tobacco-specific N-nitrosamines in F344 rats. Hoffmann, D., Rivenson, A., Amin, S., Hecht, S.S. J. Cancer Res. Clin. Oncol. (1984) [Pubmed]
  22. Predicting the mutagenicity of tobacco-related N-nitrosamines in humans using 11 strains of Salmonella typhimurium YG7108, each coexpressing a form of human cytochrome P450 along with NADPH-cytochrome P450 reductase. Fujita, K., Kamataki, T. Environ. Mol. Mutagen. (2001) [Pubmed]
  23. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by human cytochrome P450 1A2 and its inhibition by phenethyl isothiocyanate. Smith, T.J., Guo, Z., Guengerich, F.P., Yang, C.S. Carcinogenesis (1996) [Pubmed]
  24. Specificity of cytochrome P450 2A3-catalyzed alpha-hydroxylation of N'-nitrosonornicotine enantiomers. Murphy, S.E., Isaac, I.S., Ding, X., McIntee, E.J. Drug Metab. Dispos. (2000) [Pubmed]
  25. The permeability of oral leukoplakia. Bánóczy, J., Squier, C.A., Kremer, M., Wertz, P.W., Kövesi, G., Szende, B., Dombi, C. Eur. J. Oral Sci. (2003) [Pubmed]
  26. Determination of N'-nitrosonornicotine in tobacco by high speed liquid chromatography. Hecht, S.S., Ornaf, R.M., Hoffmann, D. Anal. Chem. (1975) [Pubmed]
  27. Radioimmunoassay of N'-nitrosonornicotine. Castonguay, A., Van Vunakins, H. Anal. Biochem. (1979) [Pubmed]
  28. Formation of genotoxic products from N-nitrosoheptamethyleneimine (NHMI), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and N'-nitrosonornicotine (NNN) by isolated rabbit lung cells. Dahl, J.E., Becher, R., Låg, M., Schuller, H.M., Dybing, E. Cell Biol. Toxicol. (1990) [Pubmed]
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