Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 22, 1992 - Issue 12
23
Views
6
CrossRef citations to date
0
Altmetric
Research Article

Rat liver microsomal metabolism of 2-halogenated 4-methylanilines

, , , , , & show all
Pages 1403-1423 | Received 02 Jan 1992, Accepted 01 Jul 1992, Published online: 22 Sep 2008

References

  • Bamberger E. Arylhydroxylamine und Arylazide, eine Parallele. Annalen 1921; 424: 233–296
  • Cashman J. R., Hanzlik R. P. Microsomal oxidation of thiobenzamide. A photometric assay for the flavin-containing monooxygenase. Biochemical Biophysical Research Communications 1981; 98: 147–153
  • Cheevep K. L., Richards D. E., Plotnick H. B. Metabolism of ortho-, meta-, and para-toluidine in the adult male rat. Toxicology and Applied Pharmacology 1980; 56: 361–369
  • Coutts R. T., Pound N. J. Preparation of an aromatic hydroxylamine and some hydroxamic acids, and their reaction with hydrochloric acid. Canadian Journal of Chemistry 1970; 48: 1859–1864
  • Daly J. W., Guroff G., Udenfriend S., Witkop B. Hydroxylation of alkyl and halogen substituted anilines and acetoanilides by microsomal hydroxylases. Biochemical Pharmacology 1968; 17: 31–36
  • Furst A., Moore R. E. Reductions with hydrazine hydrate catalyzed by Raney nickel. II. Aromatic compounds to intermediate products. Journal of the American Chemical Society 1957; 79: 5492–5493
  • Gorrod J. W., Gooderham N. J. Microsomal N- and C-oxidation of 4-substituted N-benzylanilines. Xenobiotica 1985; 15: 1021–1031
  • Gorrod J. W., Manson D. The metabolism of aromatic imines. Xenobiotica 1986; 16: 933–955
  • Hecht S. S., El-Bayoumy K., Tulley L., LaVoie E. Structure-mutagenicity relationships of N-oxidized derivatives of aniline, o-toluidine, 2′-methyl-4-aminobiphenyl, and 3,2′-dimethyl-4-aminobiphenyl. Journal of Medicinal Chemistry 1979; 22: 981–937
  • Herr F., Kiese M. Bestimmung von Nitrosobenzol im Blute. Naunyn-Schmiedebergs Archiv fuer experimentelle Pathologie und Pharmakologie 1959; 235: 351–353
  • Holmes R. R., Bayer R. P. A simple method for the direct oxidation of aromatic amines to nitroso compounds. Journal of the American Chemical Society 1960; 82: 3454–3456
  • Kennedy R. J., Stock A. M. The oxidation of organic substances by potassium peroximonosulfate. Journal of Organic Chemistry 1960; 25: 1901–1906
  • Kiese M. The effect of certain substituents upon the N-oxidation of aniline in vivo. Naunyn-Schmiedebergs Archiv fuer experimentelle Pathologie und Pharmakologie 1963; 244: 387–404
  • Knowles C. O., Sen Gupta A. K. N-(4-chloro-o-tolyl)-N,N-dimethylformamidine-14C (Galecron) and 4-chloro-o-toluidine-14C metabolism in the white rat. Journal of Economic Entomology 1970; 63: 856–859
  • Lal B., Gidwani R. M., Reden J., De Souza N. J. Regiospecific oxidation by DDQ of unhindered alkyl groups in sterically hindered aromatic amines. Tetrahedron Letters 1984; 25: 2901–2904
  • Lenk W., Riedl M. N-hydroxy-N-arylacetamides. V. Differences in the mechanism of haemoglobin oxidation in vitro by N-hydroxy-4-chloroacetanilide and N-hydroxy-4-chloraniline. Xenobiotica 1989; 19: 453–475
  • Leslie C., Reidy G. F., Murray M., Stacey N. H. Induction of xenobiotic biotransformation by the insecticide chlordimeform, a metabolite 4-chloro-o-toluidine and a structurally related chemical o-toluidine. Biochemical Pharmacology 1988; 37: 2529–2535
  • Rietjens I. M. C. M., Vervoort J. Microsomal metabolism of fluoroanilines. Xenobiotica 1989; 19: 1297–1305
  • Schenker E. Neuere Methoden der präparativen organischen Chemie IV. Anwendung von komplexen Borhydriden und von Diboran in der organischen Chemie. Angewandte Chemie 1961; 73: 81–124
  • Son O. S., Everett D. W., Fiala E. S. Metabolism of o-[methyl-14C]toluidine in the F344 rat. Xenobiotica 1980; 10: 457–468
  • Stavenuiter J. F. C., Verrips-Kroon M., Bos E. J., Westra J. G. Synthesis of 5-phenyl-2-pyridinamine, a possible carcinogenic pyrolysis product of phenylalanine, and some of its putative metabolites. Carcinogenesis 1985; 6: 13–19
  • Vervoort J., de Jager P. A., Steenbergen J., Rietjens I. M. C. M. Development of a 19F-n.m.r. method for studies on the in vivo and in vitro metabolism of 2-fluoroaniline. Xenobiotica 1990; 20: 657–670
  • Vogel A. I. Textbook of Practical Organic Chemistry. 5th edn. Longman, London 1989
  • Wade K. E., Troke J., Macdonald C. M., Wilson I. D., Nicholson J. K. 19F NMR studies of the metabolism of trifluoromethylaniline. Bioanalysis of drugs and metabolites, E. Reid, J. D. Robinson, I. Wilson. Plenum, New York 1988; 383–388
  • Weisburger E. K., Russfield A. B., Homburger F., Weisburger J. H., Boger E., van Dongen C. G., Chu K. C. Testing of twenty-one environmental aromatic amines or derivatives for long-term toxicity or carcinogenicity. Journal of Environmental Pathology and Toxicology 1978; 2: 325–356
  • Weisburger J. H., Weisburger E. K. Biochemical formation and pharmacological, toxicological, and pathological properties of hydroxylamines and hydroxamic acids. Pharmacological Reviews 1973; 25: 1–66
  • Yoshimi N., Sugie S., Iwata H., Niwa K., Mori H., Hashida C., Shimizu H. The genotoxicity of a variety of aniline derivatives in a DNA repair test with primary cultured rat hepatocytes. Mutation Research 1988; 206: 183–191
  • Zimmer D., Mazurek J., Petzold G., Bhuyan B. K. Bacterial mutagenicity and mammalian cell DNA damage by several substituted anilines. Mutation Research 1980; 77: 317–326

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.