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Chemical Compound Review

Nitrosamines     nitrous amide

Synonyms: Nitrosamide, Nitrosamine, nitrosoamine, AG-F-23227, CHEBI:35803, ...
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Disease relevance of nitrous amide


Psychiatry related information on nitrous amide

  • The effects of chronic alcohol consumption on nitrosamine metabolism in vivo, DNA synthesis and repair, and carcinogen-induced preneoplasia were studied in rat liver [6].
  • This test, which monitors 24-hr-excretion of urinary N-nitrosamino acids, is now applied in clinical and field studies, with the aim of measuring nitrosamine exposure and of identifying dietary, life-style, and host factors, or disease states, that affect nitrosation in man [7].
  • OBJECTIVE: To predict the impact on tobacco use in the US of a "harm reduction" policy that requires that the smokeless tobacco product meet low nitrosamine standards, but could be marketed with a warning label consistent with the evidence of relative health risks [8].

High impact information on nitrous amide


Chemical compound and disease context of nitrous amide


Biological context of nitrous amide


Anatomical context of nitrous amide

  • A tobacco-specific N-nitrosamine or cigarette smoke condensate causes neoplastic transformation of xenotransplanted human bronchial epithelial cells [22].
  • These observations, together with the available data on carcinogenicity of the nitrosamine in the rat and rabbit, suggest that in the esophagus, at least, metabolic activation of NMBZA is necessary to elicit its toxic and/or carcinogenic effect [23].
  • High-affinity nitrosamine dealkylase system in rat liver microsomes and its induction by fasting [24].
  • 4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a major nitrosamine formed in tobacco smoke, induces a high incidence of lung, liver, and nasal cavity tumors in rats [25].
  • Using a method for nitrosamine analysis that gives high recovery values and that is free from artifactual synthesis of nitrosamines, we have shown that human feces do not contain volatile nitrosamines (detection limit, 0.1 to 0.5 microgram/kg) [26].

Associations of nitrous amide with other chemical compounds


Gene context of nitrous amide

  • Results showed that 8 of 28 (28%) and 6 of 13 (46%) of the Fhit -/- and +/-, respectively, versus 2 of 25 (8%) Fhit +/+ mice developed invasive carcinoma after treatment with N-butyl-N-(4-hydroxybutyl) nitrosamine [32].
  • The tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone (NNK) is a potential human carcinogen that is known to be metabolized to DNA-reactive intermediates by the cytochromes P450 [33].
  • CYP2A6/2A7 and CYP2E1 expression in human oesophageal mucosa: regional and inter-individual variation in expression and relevance to nitrosamine metabolism [34].
  • The purpose of the current investigation was to characterize the expression of p16 and p15 in lung tumors and tumor-derived cell lines induced in A/J mice by exposure to the tobacco-specific nitrosamine, 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) [35].
  • The results of experiments using mice which were treated with NNK, a carcinogenic nitrosamine contained in tobacco smoke, together with 8-methoxypsolaren, a strong inhibitor of CYP2A6, indicated that the inhibition of CYP2A6 completely abolished the occurrence of adenoma [36].

Analytical, diagnostic and therapeutic context of nitrous amide

  • Gas chromatography and nitrosamine-selective detection, with confirmation by mass spectrometry, were used in the analyses, which were performed without knowledge of the origin of the urine samples [37].
  • The tumor, a primary one induced by chronic administration of the nitrosamine N-nitro-bis(2-hydroxyproyl) amine, is a well-differentiated adenocarcinoma that can be propagated by transplantation in syngeneic hamsters [1].
  • The metabolites present in the culture media were separated by high performance liquid chromatography and were identified by comparison to standards. alpha-Hydroxylation of NNN, an esophageal carcinogen, was the major pathway for metabolism of this nitrosamine in both tissues [38].
  • We conclude from these results that dithiocarbamates may be suitable compounds for chemoprevention of nitrosamine-induced tumors [39].
  • Increased urinary nitrosamine excretion in patients with urinary diversions [40].


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  3. Differential screening of a human chromosome 3 library identifies hepatocyte growth factor-like/macrophage-stimulating protein and its receptor in injured lung. Possible implications for neuroendocrine cell survival. Willett, C.G., Smith, D.I., Shridhar, V., Wang, M.H., Emanuel, R.L., Patidar, K., Graham, S.A., Zhang, F., Hatch, V., Sugarbaker, D.J., Sunday, M.E. J. Clin. Invest. (1997) [Pubmed]
  4. Carcinogenicity of N-nitrosomethyl(2-oxobutyl)amine and N-nitrosomethyl-(3-oxobutyl)amine in Syrian hamsters with special reference to the pancreas. Pour, P.M., Nagel, D., Lawson, T. Cancer Res. (1983) [Pubmed]
  5. Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis. Liston, B.W., Nines, R., Carlton, P.S., Gupta, A., Aziz, R., Frankel, W., Stoner, G.D. Cancer Res. (2003) [Pubmed]
  6. The mechanism of cocarcinogenic action of ethanol in rat liver. Schwarz, M., Buchmann, A., Moore, M., Kunz, W. IARC Sci. Publ. (1984) [Pubmed]
  7. Urinary N-nitrosamino acids as indices of endogenous formation of N-nitroso compounds. Ohshima, H., Pignatelli, B., Nair, J., Munoz, N., Calmels, S., Crespi, M., Lu, S.H., Bhide, S.V., Vincent, P., Leclerc, H. Basic Life Sci. (1986) [Pubmed]
  8. The potential impact of a low-nitrosamine smokeless tobacco product on cigarette smoking in the United States: estimates of a panel of experts. Levy, D.T., Mumford, E.A., Cummings, K.M., Gilpin, E.A., Giovino, G.A., Hyland, A., Sweanor, D., Warner, K.E., Compton, C. Addictive behaviors. (2006) [Pubmed]
  9. Reduction in responsiveness of thymocytes to phytohemagglutinin during bladder tumor induction and restorative effects of thymosin fraction 5 in rats. Wada, S., Kinoshita, Y., Ozaki, Y., Nishio, S., Kimura, S., Maekawa, M. J. Natl. Cancer Inst. (1987) [Pubmed]
  10. Epithelial focus assay for early detection of carcinogen-altered cells in various organs of rats exposed in situ to N-nitrosoheptamethyleneimine. Terzaghi, M., Nettesheim, P., Yarita, T., Williams, M.L. J. Natl. Cancer Inst. (1981) [Pubmed]
  11. Kinetics of nitrosamine formation in the presence of micelle-forming surfactants. Okun, J.D., Archer, M.C. J. Natl. Cancer Inst. (1977) [Pubmed]
  12. Effect of cimetidine on gastric juice N-nitrosamine concentration. Reed, P.I., Smith, P.L., Haines, K., House, F.R., Walters, C.L. Lancet (1981) [Pubmed]
  13. 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]
  14. Nitrite and nitrosamine synthesis by hepatocytes isolated from normal woodchucks (Marmota monax) and woodchucks chronically infected with woodchuck hepatitis virus. Liu, R.H., Jacob, J.R., Tennant, B.C., Hotchkiss, J.H. Cancer Res. (1992) [Pubmed]
  15. HPV-16, tobacco-specific N-nitrosamine, and N-methyl-N'-nitro-N-nitrosoguanidine in oral carcinogenesis. Kim, M.S., Shin, K.H., Baek, J.H., Cherrick, H.M., Park, N.H. Cancer Res. (1993) [Pubmed]
  16. Carcinogenicity of hydroxylated alkylnitrosoureas and of nitrosooxazolidones by mouse skin painting and by gavage in rats. Lijinsky, W., Reuber, M.D. Cancer Res. (1983) [Pubmed]
  17. Gastric-juice nitrite. A risk factor for cancer in the hypochlorhydric stomach? Ruddell, W.S., Bone, E.S., Hill, M.J., Blendis, L.M., Walters, C.L. Lancet (1976) [Pubmed]
  18. Modulation of the uptake and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by nicotine in hamster lung. Schuller, H.M., Castonguay, A., Orloff, M., Rossignol, G. Cancer Res. (1991) [Pubmed]
  19. Angiotensin II type 2 receptor gene deficiency attenuates susceptibility to tobacco-specific nitrosamine-induced lung tumorigenesis: involvement of transforming growth factor-beta-dependent cell growth attenuation. Kanehira, T., Tani, T., Takagi, T., Nakano, Y., Howard, E.F., Tamura, M. Cancer Res. (2005) [Pubmed]
  20. Use of 3,4-dichlorobenzenethiol as a trapping agent for alkylating intermediates during in vitro metabolism of nitrosamines. Kroeger-Koepke, M.B., Michejda, C.J., Roller, P.P., Keefer, L.K. Cancer Res. (1985) [Pubmed]
  21. Esophageal microsomal metabolism of N-nitrosomethylbenzylamine in the zinc-deficient rat. Barch, D.H., Kuemmerle, S.C., Hollenberg, P.F., Iannaccone, P.M. Cancer Res. (1984) [Pubmed]
  22. A tobacco-specific N-nitrosamine or cigarette smoke condensate causes neoplastic transformation of xenotransplanted human bronchial epithelial cells. Klein-Szanto, A.J., Iizasa, T., Momiki, S., Garcia-Palazzo, I., Caamano, J., Metcalf, R., Welsh, J., Harris, C.C. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  23. Organ specificity in the microsomal activation and toxicity of N-nitrosomethylbenzylamine in various species. Mehta, R., Labuc, G.E., Urbanski, S.J., Archer, M.C. Cancer Res. (1984) [Pubmed]
  24. High-affinity nitrosamine dealkylase system in rat liver microsomes and its induction by fasting. Tu, Y.Y., Yang, C.S. Cancer Res. (1983) [Pubmed]
  25. Accumulation and persistence of DNA adducts in respiratory tissue of rats following multiple administrations of the tobacco specific carcinogen 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. Belinsky, S.A., White, C.M., Boucheron, J.A., Richardson, F.C., Swenberg, J.A., Anderson, M. Cancer Res. (1986) [Pubmed]
  26. Absence of volatile nitrosamines in human feces. Lee, L., Archer, M.C., Bruce, W.R. Cancer Res. (1981) [Pubmed]
  27. Treatment of nitrosamine-induced pancreatic tumors in hamsters with analogs of somatostatin and luteinizing hormone-releasing hormone. Paz-Bouza, J.I., Redding, T.W., Schally, A.V. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  28. Transplacental induction of pancreas tumors in hamsters by ethanol and the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Schüller, H.M., Jorquera, R., Reichert, A., Castonguay, A. Cancer Res. (1993) [Pubmed]
  29. Comparative study of DNA damage and repair induced by ten N-nitroso compounds in primary cultures of human and rat hepatocytes. Martelli, A., Robbiano, L., Gazzaniga, G.M., Brambilla, G. Cancer Res. (1988) [Pubmed]
  30. An investigation of whether polymorphisms of cytochrome P4502E1 are genetic markers of susceptibility to alcoholic end-stage organ damage in a Chinese population. Chao, Y.C., Young, T.H., Chang, W.K., Tang, H.S., Hsu, C.T. Hepatology (1995) [Pubmed]
  31. A sensitive hepatocyte-mediated assay for the metabolism of nitrosamines to mutagens for mammalian cells. Jones, C.A., Huberman, E. Cancer Res. (1980) [Pubmed]
  32. Inactivation of the FHIT gene favors bladder cancer development. Vecchione, A., Sevignani, C., Giarnieri, E., Zanesi, N., Ishii, H., Cesari, R., Fong, L.Y., Gomella, L.G., Croce, C.M., Baffa, R. Clin. Cancer Res. (2004) [Pubmed]
  33. Human CYP2A6 activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK): mutational specificity in the gpt gene of AS52 cells. Tiano, H.F., Wang, R.L., Hosokawa, M., Crespi, C., Tindall, K.R., Langenbach, R. Carcinogenesis (1994) [Pubmed]
  34. CYP2A6/2A7 and CYP2E1 expression in human oesophageal mucosa: regional and inter-individual variation in expression and relevance to nitrosamine metabolism. Godoy, W., Albano, R.M., Moraes, E.G., Pinho, P.R., Nunes, R.A., Saito, E.H., Higa, C., Filho, I.M., Kruel, C.D., Schirmer, C.C., Gurski, R., Lang, M.A., Pinto, L.F. Carcinogenesis (2002) [Pubmed]
  35. Deletion and differential expression of p16INK4a in mouse lung tumors. Belinsky, S.A., Swafford, D.S., Middleton, S.K., Kennedy, C.H., Tesfaigzi, J. Carcinogenesis (1997) [Pubmed]
  36. Enticed into molecular toxicology. Kamataki, T. Yakugaku Zasshi (2006) [Pubmed]
  37. Metabolites of a tobacco-specific carcinogen in urine from newborns. Lackmann, G.M., Salzberger, U., Töllner, U., Chen, M., Carmella, S.G., Hecht, S.S. J. Natl. Cancer Inst. (1999) [Pubmed]
  38. 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]
  39. Influence of dithiocarbamates on the metabolism and toxicity of N-nitrosodimethylamine in rats. Frank, N., Bertram, B., Scherf, H.R., Wiessler, M. Carcinogenesis (1990) [Pubmed]
  40. Increased urinary nitrosamine excretion in patients with urinary diversions. Tricker, A.R., Kälble, T., Preussmann, R. Carcinogenesis (1989) [Pubmed]
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