The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

NITROSOBENZENE     nitrosobenzene

Synonyms: CHEMBL98797, N24609_ALDRICH, AG-G-07892, ACMC-209m6j, CHEBI:27986, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of nitrosobenzene


High impact information on nitrosobenzene


Biological context of nitrosobenzene

  • Diels-Alder reaction of thebaine (1) and N-(cyclopropylmethyl)northebaine with nitrosobenzene and p-fluoronitrosobenzene gave adducts [6,14-exo-(phenyloxyamino)codeine 6-methyl esther and derivatives, 2a-d] which yielded 14-(phenylhydroxyamino)codeinone and derivatives (3a-d) on acid hydrolysis [7].
  • From shapes of the kinetic curves analyzed on the basis of the Avrami model, it was found that phase transfer could be triggered by a dimerization reaction of para-substituted nitrosobenzene to azodioxide, which, in turn, can be caused by different packing factors such as disorder in the starting nitroso monomer crystals [8].
  • These results suggest that nitrosobenzene can be reduced non-enzymatically by NADH, and the redox cycle reaction resulted in oxidative DNA damage due to the copper-oxygen complex, derived from the reaction of Cu(I) with H2O2 [9].
  • Biotransformation of nitrosobenzene, phenylhydroxylamine, and aniline in the isolated perfused rat liver [10].
  • Aromatic nitroso-compounds such as nitrosobenzene inhibited the respiratory burst of intact neutrophils induced by various stimulants, including phorbol 12-myristate 13-acetate and a chemotactic peptide [11].

Anatomical context of nitrosobenzene


Associations of nitrosobenzene with other chemical compounds


Gene context of nitrosobenzene


Analytical, diagnostic and therapeutic context of nitrosobenzene


  1. Contribution of nitrosobenzene to splenic toxicity of aniline. Khan, M.F., Wu, X., Ansari, G.A. J. Toxicol. Environ. Health Part A (2000) [Pubmed]
  2. Aniline-, phenylhydroxylamine-, nitrosobenzene-, and nitrobenzene-induced hemoglobin thiyl free radical formation in vivo and in vitro. Maples, K.R., Eyer, P., Mason, R.P. Mol. Pharmacol. (1990) [Pubmed]
  3. Contribution of aniline metabolites to aniline-induced methemoglobinemia. Harrison, J.H., Jollow, D.J. Mol. Pharmacol. (1987) [Pubmed]
  4. Direct detection of the sulfur trioxide radical anion during the horseradish peroxidase-hydrogen peroxide oxidation of sulfite (aqueous sulfur dioxide). Mottley, C., Trice, T.B., Mason, R.P. Mol. Pharmacol. (1982) [Pubmed]
  5. Formation of N-hydroxy-N-arylacetamides from nitroso aromatic compounds by the mammalian pyruvate dehydrogenase complex. Yoshioka, T., Uematsu, T. Biochem. J. (1993) [Pubmed]
  6. Cumene hydroperoxide-dependent oxidation of NNN'N'-tetramethyl-p-phenylenediamine and 7-ethoxycoumarin by cytochrome P-450. Comparison between the haemoproteins from liver and olfactory tissue. Reed, C.J., De Matteis, F. Biochem. J. (1989) [Pubmed]
  7. 14-(Arylhydroxyamino)codeinones and derivatives as analgetics and antagonists. Schwab, L.S. J. Med. Chem. (1980) [Pubmed]
  8. Nitrosobenzene dimerizations as a model system for studying solid-state reaction mechanisms. Vancik, H., Simunic-Meznaric, V., Mestrovic, E., Halasz, I. J. Org. Chem. (2004) [Pubmed]
  9. Oxidative DNA damage by a metabolite of carcinogenic and reproductive toxic nitrobenzene in the presence of NADH and Cu(II). Ohkuma, Y., Kawanishi, S. Biochem. Biophys. Res. Commun. (1999) [Pubmed]
  10. Biotransformation of nitrosobenzene, phenylhydroxylamine, and aniline in the isolated perfused rat liver. Eyer, P., Kampffmeyer, H., Maister, H., Rösch-Oehme, E. Xenobiotica (1980) [Pubmed]
  11. Effect of aromatic nitroso-compounds on superoxide-generating activity in neutrophils. Nakata, M., Nasuda-Kouyama, A., Isogai, Y., Kanegasaki, S., Iizuka, T. J. Biochem. (1997) [Pubmed]
  12. Oxidative degradation of haemoglobin by nitrosobenzene in the erythrocyte. Hirota, K., Itano, H.A., Vedvick, T.S. Biochem. J. (1978) [Pubmed]
  13. In vivo EPR studies of the metabolic fate of nitrosobenzene in the mouse. Fujii, H., Zhao, B., Koscielniak, J., Berliner, L.J. Magnetic resonance in medicine : official journal of the Society of Magnetic Resonance in Medicine / Society of Magnetic Resonance in Medicine. (1994) [Pubmed]
  14. T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome. Wulferink, M., González, J., Goebel, C., Gleichmann, E. Chem. Res. Toxicol. (2001) [Pubmed]
  15. Nitrobenzene potential human cancer risk based on animal studies. Holder, J.W. Toxicology and industrial health. (1999) [Pubmed]
  16. Formation of complexes between microsomal cytochrome P-450-Fe(II) and nitrosoarenes obtained by oxidation of arylhydroxylamines or reduction of nitroarenes in situ. Mansuy, D., Beaune, P., Cresteil, T., Bacot, C., Chottard, J.C., Gans, P. Eur. J. Biochem. (1978) [Pubmed]
  17. N-phenylglycolhydroxamate production by the action of transketolase on nitrosobenzene. Corbett, M.D., Chipko, B.R. Biochem. J. (1977) [Pubmed]
  18. Nitroxyl analogs as inhibitors of aldehyde dehydrogenase. C-nitroso compounds. Nagasawa, H.T., Yost, Y., Elberling, J.A., Shirota, F.N., DeMaster, E.G. Biochem. Pharmacol. (1993) [Pubmed]
  19. Biological reduction of aromatic nitroso compounds: evidence for the involvement of superoxide anions. Fujii, H., Koscielniak, J., Kakinuma, K., Berliner, L.J. Free Radic. Res. (1994) [Pubmed]
  20. Enzymatic and mechanistic studies on the formation of N-phenylglycolohydroxamic acid from nitrosobenzene and pyruvate in spinach leaf homogenate. Tatsunami, R., Yoshioka, T. J. Agric. Food Chem. (2006) [Pubmed]
  21. Exposure of mice to the nitroso metabolite of sulfamethoxazole stimulates interleukin 5 production by CD4+ T-cells. Hopkins, J.E., Naisbitt, D.J., Humphreys, N., Dearman, R.J., Kimber, I., Park, B.K. Toxicology (2005) [Pubmed]
  22. Participation of cytochrome P-450 in the reduction of nitro compounds by rat liver microsomes. Harada, N., Omura, T. J. Biochem. (1980) [Pubmed]
  23. Comparison of antioxidant properties of nifedipine and illuminated nifedipine with nitroso spin traps in low density lipoproteins and phosphatidylcholine liposomes. Ondrias, K., Misík, V., Stasko, A., Gergel, D., Hromadová, M. Biochim. Biophys. Acta (1994) [Pubmed]
  24. Substrate free radicals are intermediates in ligninase catalysis. Hammel, K.E., Kalyanaraman, B., Kirk, T.K. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  25. Bioassay for carcinogenicity of 3,2'-dimethyl-4-nitrosobiphenyl, O-nitrosotoluene, nitrosobenzene and the corresponding amines in Syrian golden hamsters. Hecht, S.S., El-Bayoumy, K., Rivenson, A., Fiala, E.S. Cancer Lett. (1983) [Pubmed]
WikiGenes - Universities