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Chemical Compound Review

nnal     N-(4-hydroxy-4-pyridin-3-yl- butyl)-N...

Synonyms: rac NNAL, CCRIS 3049, AG-H-03176, LS-7522, AC1L2XMK, ...
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Disease relevance of CCRIS 3049


Psychiatry related information on CCRIS 3049


High impact information on CCRIS 3049


Biological context of CCRIS 3049


Anatomical context of CCRIS 3049


Associations of CCRIS 3049 with other chemical compounds


Gene context of CCRIS 3049


Analytical, diagnostic and therapeutic context of CCRIS 3049

  • HPLC analysis revealed the presence of 4-hydroxy-4-(3-pyridyl)butyric acid (hydroxy acid), 4-oxo-4-(3-pyridyl)-butyric acid (keto acid), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butyl beta-D-glucopyranosiduronic acid (NNAL Glu), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) and NNK [21].


  1. Transport of the beta -O-glucuronide conjugate of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by the multidrug resistance protein 1 (MRP1). Requirement for glutathione or a non-sulfur-containing analog. Leslie, E.M., Ito , K., Upadhyaya, P., Hecht, S.S., Deeley, R.G., Cole, S.P. J. Biol. Chem. (2001) [Pubmed]
  2. A study of tobacco carcinogenesis. LI. Relative potencies of tobacco-specific N-nitrosamines as inducers of lung tumours in A/J mice. Hoffmann, D., Djordjevic, M.V., Rivenson, A., Zang, E., Desai, D., Amin, S. Cancer Lett. (1993) [Pubmed]
  3. Smoking behaviour and toxin exposure during six weeks use of a potential reduced exposure product: Omni. Hughes, J.R., Hecht, S.S., Carmella, S.G., Murphy, S.E., Callas, P. Tobacco control. (2004) [Pubmed]
  4. 11Beta-hydroxysteroid dehydrogenase responsible for carbonyl reduction of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mouse lung microsomes. Maser, E. Cancer Res. (1998) [Pubmed]
  5. Effects of phenethyl isothiocyanate on the tissue distribution of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and metabolites in F344 rats. Staretz, M.E., Hecht, S.S. Cancer Res. (1995) [Pubmed]
  6. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in human lung and liver microsomes and cytochromes P-450 expressed in hepatoma cells. Smith, T.J., Guo, Z., Gonzalez, F.J., Guengerich, F.P., Stoner, G.D., Yang, C.S. Cancer Res. (1992) [Pubmed]
  7. Placental transfer of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone instilled intratracheally in Syrian golden hamsters. Jorquera, R., Castonguay, A., Schuller, H.M. Cancer Res. (1992) [Pubmed]
  8. Effects of indole-3-carbinol on lung tumorigenesis and DNA methylation induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and on the metabolism and disposition of NNK in A/J mice. Morse, M.A., LaGreca, S.D., Amin, S.G., Chung, F.L. Cancer Res. (1990) [Pubmed]
  9. DNA and hemoglobin alkylation by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and its major metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F344 rats. Hecht, S.S., Trushin, N. Carcinogenesis (1988) [Pubmed]
  10. Analysis of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in urine by extraction on a molecularly imprinted polymer column and liquid chromatography/atmospheric pressure ionization tandem mass spectrometry. Xia, Y., McGuffey, J.E., Bhattacharyya, S., Sellergren, B., Yilmaz, E., Wang, L., Bernert, J.T. Anal. Chem. (2005) [Pubmed]
  11. Synthesis of stereospecifically deuterated 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) iastereomers and metabolism by A/J mouse lung microsomes and cytochrome p450 2A5. Jalas, J.R., Hecht, S.S. Chem. Res. Toxicol. (2003) [Pubmed]
  12. Mass spectrometric quantitation of nicotine, cotinine, and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human toenails. Stepanov, I., Feuer, R., Jensen, J., Hatsukami, D., Hecht, S.S. Cancer Epidemiol. Biomarkers Prev. (2006) [Pubmed]
  13. Identification of tobacco-derived compounds in human pancreatic juice. Prokopczyk, B., Hoffmann, D., Bologna, M., Cunningham, A.J., Trushin, N., Akerkar, S., Boyiri, T., Amin, S., Desai, D., Colosimo, S., Pittman, B., Leder, G., Ramadani, M., Henne-Bruns, D., Beger, H.G., El-Bayoumy, K. Chem. Res. Toxicol. (2002) [Pubmed]
  14. Low levels of expression of cytochromes P-450 in normal and cancerous fetal pancreatic tissues of hamsters treated with NNK and/or ethanol. Zhang, L., Weddle, D.L., Thomas, P.E., Zheng, B., Castonguay, A., Schuller, H.M., Miller, M.S. Toxicol. Sci. (2000) [Pubmed]
  15. Effects of long term dietary phenethyl isothiocyanate on the microsomal metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in F344 rats. Staretz, M.E., Koenig, L.A., Hecht, S.S. Carcinogenesis (1997) [Pubmed]
  16. Effect of nicotine or cotinine on metabolism of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in isolated rat lung and liver. Schulze, J., Schrader, E., Foth, H., Kahl, G.F., Richter, E. Naunyn Schmiedebergs Arch. Pharmacol. (1998) [Pubmed]
  17. Comparative metabolism of the tobacco-related carcinogens benzo[a]pyrene, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol, and N'- nitrosonornicotine in human hepatic microsomes. Staretz, M.E., Murphy, S.E., Patten, C.J., Nunes, M.G., Koehl, W., Amin, S., Koenig, L.A., Guengerich, F.P., Hecht, S.S. Drug Metab. Dispos. (1997) [Pubmed]
  18. Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by rat UDP-glucuronosyltransferase 2B1. Ren, Q., Murphy, S.E., Dannenberg, A.J., Park, J.Y., Tephly, T.R., Lazarus, P. Drug Metab. Dispos. (1999) [Pubmed]
  19. Characterization of N-glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human liver: importance of UDP-glucuronosyltransferase 1A4. Wiener, D., Doerge, D.R., Fang, J.L., Upadhyaya, P., Lazarus, P. Drug Metab. Dispos. (2004) [Pubmed]
  20. Comparative metabolism of the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol by rat cytochrome P450 2A3 and human cytochrome P450 2A13. Jalas, J.R., Ding, X., Murphy, S.E. Drug Metab. Dispos. (2003) [Pubmed]
  21. Biliary excretion of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in the rat. Schulze, J., Richter, E., Binder, U., Zwickenpflug, W. Carcinogenesis (1992) [Pubmed]
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