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Chemical Compound Review

SureCN8277     N,N-dimethylaniline

Synonyms: LS-21, AGN-PC-00JR8T, AGN-PC-00JY1U, CHEMBL371654, NSC-7195, ...
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Disease relevance of HSDB 1179


High impact information on HSDB 1179

  • Complementary DNA (cDNA) clones encoding the adult human liver flavin-containing monooxygenase (FMO; dimethylaniline N-oxidase, EC were isolated from lambda gt10 and lambda gt11 libraries [4].
  • Ferric chloride-catalyzed activation of hydrogen peroxide for the demethylation of N,N-dimethylaniline, the epoxidation of olefins, and the oxidative cleavage of vicinal diols in acetonitrile: a reaction mimic for cytochrome P-450 [5].
  • When the concentrations of both N,N-dimethylaniline and ethyl hydroperoxide were varied in a constant ratio a linear double reciprocal plot was obtained, which is consistent with a ping-pong kinetic mechanism for the horseradish peroxidase-catalyzed demethylation reaction [6].
  • The dealkylation reaction exhibited normal Michaelis-Menten saturation kinetics with respect to N,N-dimethylaniline (Km = 0.08 mM) and ethyl hydrogen peroxide (Km = 0.8 mM) at low substrate concentrations [7].
  • Addition of saturating amounts of N,N-dimethylaniline leads to a 3-fold increase of Vmax of NADPH utilization with 40% of these extra molecules providing electrons for the hydroxylation/N-demethylation sequence [8].

Biological context of HSDB 1179


Anatomical context of HSDB 1179


Associations of HSDB 1179 with other chemical compounds


Gene context of HSDB 1179


Analytical, diagnostic and therapeutic context of HSDB 1179


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  2. Subchronic (13-week) toxicity studies of N,N-dimethylaniline administered to Fischer 344 rats and B6C3F1 mice. Abdo, K.M., Jokinen, M.P., Hiles, R. Journal of toxicology and environmental health. (1990) [Pubmed]
  3. Effect of intrahepatic arterial infusion of 131I-labelled lipiodol on hepatocellular carcinoma of rat. Tsai, C., Kusumoto, Y., Harada, R., Shima, M., Nakata, K., Kono, K., Sato, A., Ishii, N., Koji, T., Nagataki, S. Ann. Acad. Med. Singap. (1986) [Pubmed]
  4. Molecular cloning of the flavin-containing monooxygenase (form II) cDNA from adult human liver. Lomri, N., Gu, Q., Cashman, J.R. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  5. Ferric chloride-catalyzed activation of hydrogen peroxide for the demethylation of N,N-dimethylaniline, the epoxidation of olefins, and the oxidative cleavage of vicinal diols in acetonitrile: a reaction mimic for cytochrome P-450. Sugimoto, H., Spencer, L., Sawyer, D.T. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  6. Characterization of the N-demethylation reactions catalyzed by horseradish peroxidase. Kedderis, G.L., Hollenberg, P.F. J. Biol. Chem. (1983) [Pubmed]
  7. N-Demethylation reactions catalyzed by chloroperoxidase. Kedderis, G.L., Koop, D.R., Hollenberg, P.F. J. Biol. Chem. (1980) [Pubmed]
  8. Studies on the autoinactivation behavior of pure, reconstituted phenobarbital-induced cytochrome P-450 isozyme from rat liver. Loosemore, M., Light, D.R., Walsh, C. J. Biol. Chem. (1980) [Pubmed]
  9. Some properties of an inhibitory cytochrome P-450 metabolic-intermediate complex existing in a spin-state equilibrium. Hlavica, P., Künzel, U., Achtert, G. Biochem. Pharmacol. (1989) [Pubmed]
  10. The influence of cholesterol incorporation and removal on lipid-bilayer viscosity and electron transfer in rat-liver microsomes. Archakov, A.I., Borodin, E.A., Dobretsov, G.E., Karasevich, E.I., Karyakin, A.V. Eur. J. Biochem. (1983) [Pubmed]
  11. Hypoxia-selective activation of 5-fluorodeoxyuridine prodrug possessing indolequinone structure: radiolytic reduction and cytotoxicity characteristics. Tanabe, K., Makimura, Y., Tachi, Y., Imagawa-Sato, A., Nishimoto, S. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  12. Re-examination of the anodic oxidation of N,N-dimethylaniline, using parametric method 3. Michida, T., Osawa, E., Yamaoka, Y. Chem. Pharm. Bull. (2000) [Pubmed]
  13. Reduction of tertiary amine N-oxides by rat liver mitochondria. Sugiura, M., Kato, R. J. Pharmacol. Exp. Ther. (1977) [Pubmed]
  14. Concurrent flavin-containing monooxygenase down-regulation and cytochrome P-450 induction by dietary indoles in rat: implications for drug-drug interaction. Katchamart, S., Stresser, D.M., Dehal, S.S., Kupfer, D., Williams, D.E. Drug Metab. Dispos. (2000) [Pubmed]
  15. Dietary selenium deficiency causes decreased N-oxygenation of N,N-dimethylaniline and increased mutagenicity of dimethylnitrosamine in the isolated rat liver/cell culture system. Olsson, U., Onfelt, A., Beije, B. Mutat. Res. (1984) [Pubmed]
  16. Influence of metabolic factors on the mutagenic effectiveness of cyclophosphamide in Drosophila melanogaster. Zijlstra, J.A., Vogel, E.W. Mutat. Res. (1989) [Pubmed]
  17. Cumene hydroperoxide supported demethylation of N,N-dimethylaniline by cytochrome P-450 from adrenal cortex mitochondria. Akhrem, A.A., Khatyleva SYu, n.u.l.l., Shkumatov, V.M., Chashchin, V.L., Kiselev, P.A. Acta Biol. Med. Ger. (1982) [Pubmed]
  18. Hydrogen-bond-mediated photoinduced electron-transfer: novel dimethylaniline-anthracene ensembles formed via Watson-Crick base-pairing. Sessler, J.L., Sathiosatham, M., Brown, C.T., Rhodes, T.A., Wiederrecht, G. J. Am. Chem. Soc. (2001) [Pubmed]
  19. Peroxidase-catalyzed N-demethylation reactions: deuterium solvent isotope effects. Kedderis, G.L., Hollenberg, P.F. Biochemistry (1985) [Pubmed]
  20. Roles of proximal ligand in heme proteins: replacement of proximal histidine of human myoglobin with cysteine and tyrosine by site-directed mutagenesis as models for P-450, chloroperoxidase, and catalase. Adachi, S., Nagano, S., Ishimori, K., Watanabe, Y., Morishima, I., Egawa, T., Kitagawa, T., Makino, R. Biochemistry (1993) [Pubmed]
  21. Cerebral flavin-containing monooxygenase-mediated metabolism of antidepressants in brain: immunochemical properties and immunocytochemical localization. Bhamre, S., Bhagwat, S.V., Shankar, S.K., Williams, D.E., Ravindranath, V. J. Pharmacol. Exp. Ther. (1993) [Pubmed]
  22. Characterization of hepatic flavin monooxygenase from the marine teleost turbot (Scophthalmus maximus L.). Peters, L.D., Livingstone, D.R., Shenin-Johnson, S., Hines, R.N., Schlenk, D. Xenobiotica (1995) [Pubmed]
  23. Polarity of lipid bilayers. A fluorescence investigation. Pérochon, E., Lopez, A., Tocanne, J.F. Biochemistry (1992) [Pubmed]
  24. Flavin-containing monooxygenase activity in human liver microsomes. McManus, M.E., Stupans, I., Burgess, W., Koenig, J.A., Hall, P.M., Birkett, D.J. Drug Metab. Dispos. (1987) [Pubmed]
  25. Genotoxicity analysis of N,N-dimethylaniline and N,N-dimethyl-p-toluidine. Taningher, M., Pasquini, R., Bonatti, S. Environ. Mol. Mutagen. (1993) [Pubmed]
  26. Nicotinoprotein [NAD(P)-containing] alcohol/aldehyde oxidoreductases. Purification and characterization of a novel type from Amycolatopsis methanolica. Van Ophem, P.W., Van Beeumen, J., Duine, J.A. Eur. J. Biochem. (1993) [Pubmed]
  27. A convenient radiometric assay for flavin-containing monooxygenase activity. Cashman, J.R. Anal. Biochem. (1987) [Pubmed]
  28. Ionization of aniline and its N-methyl and N-phenyl substituted derivatives by (free) electron transfer to n-butyl chloride parent radical cations. Maroz, A., Hermann, R., Naumov, S., Brede, O. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
  29. Lidocaine in the horse: its pharmacological effects and their relationship to analytical findings. Harkins, J.D., Mundy, G.D., Woods, W.E., Lehner, A., Karpiesiuk, W., Rees, W.A., Dirikolu, L., Bass, S., Carter, W.G., Boyles, J., Tobin, T. J. Vet. Pharmacol. Ther. (1998) [Pubmed]
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