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Chemical Compound Review

MOCA     4-[(4-amino-3-chloro- phenyl)methyl]-2...

Synonyms: Bisamine, Cyanaset, Quodorole, Dacpm, MBOCA, ...
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Disease relevance of 4,4'-METHYLENEBIS(2-CHLOROANILINE)


High impact information on 4,4'-METHYLENEBIS(2-CHLOROANILINE)


Biological context of 4,4'-METHYLENEBIS(2-CHLOROANILINE)


Anatomical context of 4,4'-METHYLENEBIS(2-CHLOROANILINE)

  • Human liver microsomes were fractionated and MOCA N-oxidation activity was monitored through the procedure [9].
  • N-Hydroxylation of MOCA occurred at a rate of 335 +/- 119 pmol/min/mg rat microsomal protein (n = 3) versus 230 or 765 (n = 2) with microsomes from humans; the product was identified by isotopic dilution for both species [13].
  • MOCA-DNA adducts have also been detected in vivo in treated rats and in exfoliated urothelium of a worker accidentally exposed to MOCA [8].
  • Beagle dogs were treated with single and multiple doses of MOCA and DNA adduct levels were determined in liver and bladder epithelium [8].
  • Mean MN frequencies were higher in urothelial cells and lymphocytes of MOCA workers (14.27 +/- 0.56 and 13.25 +/- 0.48 MN/1000 cells) than in controls (6.90 +/- 0.18 and 9.24 +/- 0.29 MN/1000 cells) [14].

Associations of 4,4'-METHYLENEBIS(2-CHLOROANILINE) with other chemical compounds



  • It is therefore of interest to identify the human cytochrome P450 (P450) enzymes involved in MOCA N-oxidation, the primary reaction involved in the formation of an electrophilic product [9].
  • Induction of ornithine decarboxylase activity by 4,4'-methylene bis(2-chloroaniline) in the rat [18].
  • In addition, prophylactic cranial irradiation was administered concurrently with thoracic irradiation to 194 patients receiving CAML-HC, VCAM, or MOCA [19].
  • METHODS: Urinary MOCA markers were measured in urine samples collected at the end of the workshifts [20].

Analytical, diagnostic and therapeutic context of 4,4'-METHYLENEBIS(2-CHLOROANILINE)


  1. Review of the genotoxicity and carcinogenicity of 4,4'-methylene-dianiline and 4,4'-methylene-bis-2-chloroaniline. McQueen, C.A., Williams, G.M. Mutat. Res. (1990) [Pubmed]
  2. Kinetics of tissue distribution and elimination of 4,4'-methylene bis(2-chloroaniline) in rats. Tobes, M.C., Brown, L.E., Chin, B., Marsh, D.D. Toxicol. Lett. (1983) [Pubmed]
  3. Urinary bladder tumors in dogs from 4,4'-methylene-bis (2-chloroaniline) (MOCA). Stula, E.F., Barnes, J.R., Sherman, H., Reinhardt, C.F., Zapp, J.A. Journal of environmental pathology and toxicology. (1978) [Pubmed]
  4. Determination of the tumorigenic potential of methylene-bis-orthochloroaniline. Kommineni, C., Groth, D.H., Frockt, I.J., Voelker, R.W., Stanovick, R.P. Journal of environmental pathology and toxicology. (1979) [Pubmed]
  5. Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4'-methylene-bis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases. Butler, M.A., Guengerich, F.P., Kadlubar, F.F. Cancer Res. (1989) [Pubmed]
  6. Role of the acetylation polymorphism in determining susceptibility of cultured rabbit hepatocytes to DNA damage by aromatic amines. McQueen, C.A., Maslansky, C.J., Williams, G.M. Cancer Res. (1983) [Pubmed]
  7. Neoplastic transformation and DNA-binding of 4,4'-methylenebis(2-chloroaniline) in SV40-immortalized human uroepithelial cell lines. Swaminathan, S., Frederickson, S.M., Hatcher, J.F., Reznikoff, C.A., Butler, M.A., Cheever, K.L., Savage, R.E. Carcinogenesis (1996) [Pubmed]
  8. 32P-postlabelling analysis of DNA adducts of 4,4'-methylenebis(2-chloroaniline) in target and nontarget tissues in the dog and their implications for human risk assessment. Segerbäck, D., Kaderlik, K.R., Talaska, G., Dooley, K.L., Kadlubar, F.F. Carcinogenesis (1993) [Pubmed]
  9. Contributions of human liver cytochrome P450 enzymes to the N-oxidation of 4,4'-methylene-bis(2-chloroaniline). Yun, C.H., Shimada, T., Guengerich, F.P. Carcinogenesis (1992) [Pubmed]
  10. Monitoring exposure to 4,4'-methylene-bis(2-chloroaniline) through the gas chromatography-mass spectrometry measurement of adducts to hemoglobin. Bailey, E., Brooks, A.G., Farmer, P.B., Street, B. Environ. Health Perspect. (1993) [Pubmed]
  11. Hydroxylation of 4,4'-methylenebis(2-chloroaniline) by canine, guinea pig, and rat liver microsomes. Chen, T.H., Kuslikis, B.I., Braselton, W.E. Drug Metab. Dispos. (1989) [Pubmed]
  12. In vitro effects of MOCA and dapsone on rat hepatic and splenic immune cells. Kelso, J.M., Bai, C.L., Ahokas, J.T., Wright, P.F. Immunopharmacology (1997) [Pubmed]
  13. Metabolism of 4,4'-methylene-bis-2-chloroaniline (MOCA) by rats in vivo and formation of N-hydroxy MOCA by rat and human liver microsomes. Morton, K.C., Lee, M.S., Siedlik, P., Chapman, R. Carcinogenesis (1988) [Pubmed]
  14. Micronuclei in peripheral lymphocytes and exfoliated urothelial cells of workers exposed to 4,4'-methylenebis-(2-chloroaniline) (MOCA). Murray, E.B., Edwards, J.W. Mutat. Res. (1999) [Pubmed]
  15. Evaluation of the rat micronucleus test with bone marrow and peripheral blood: summary of the 9th collaborative study by CSGMT/JEMS. MMS. Collaborative Study Group for the Micronucleus Test. Environmental Mutagen Society of Japan. Mammalian Mutagenicity Study Group. Wakata, A., Miyamae, Y., Sato, S., Suzuki, T., Morita, T., Asano, N., Awogi, T., Kondo, K., Hayashi, M. Environ. Mol. Mutagen. (1998) [Pubmed]
  16. Immunochemical, 32P-postlabeling, and GC/MS detection of 4-aminobiphenyl-DNA adducts in human peripheral lung in relation to metabolic activation pathways involving pulmonary N-oxidation, conjugation, and peroxidation. Culp, S.J., Roberts, D.W., Talaska, G., Lang, N.P., Fu, P.P., Lay, J.O., Teitel, C.H., Snawder, J.E., Von Tungeln, L.S., Kadlubar, F.F. Mutat. Res. (1997) [Pubmed]
  17. Simultaneous determination of 2,4- and 2,6-diisocyanatotoluene (TDI) and 3,3'-dichloro-4,4'-diaminodiphenylmethane (MOCA) in air. Ebell, G.F., Fleming, D.E., Genovese, J.H., Taylor, G.A. The Annals of occupational hygiene. (1980) [Pubmed]
  18. Induction of ornithine decarboxylase activity by 4,4'-methylene bis(2-chloroaniline) in the rat. Savage, R.E., Weigel, W.W., Krieg, E.F. Cancer Lett. (1992) [Pubmed]
  19. A 10-year experience with combined modality therapy for stage III small cell lung carcinoma. Jacobs, R.H., Greenburg, A., Bitran, J.D., Hoffman, P.C., Albain, K.S., Desser, R., Potkul, L., Golomb, H.M. Cancer (1986) [Pubmed]
  20. Biological monitoring of workers exposed to 4,4'-methylene-bis-(2-orthochloroaniline) (MOCA). II. Comparative interest of "free" and "total" MOCA in the urine of exposed workers. Robert, A., Ducos, P., Francin, J.M. International archives of occupational and environmental health. (1999) [Pubmed]
  21. Determination of 4,4'-methylenebis(2-chloroaniline) in urine by liquid chromatography with ion-paired solid-phase extraction and electrochemical detection. Okayama, A., Ichikawa, Y., Yoshida, M., Hara, I., Morimoto, K. Clin. Chem. (1988) [Pubmed]
  22. Covalent binding of 4,4'-methylenebis-(2-chloroaniline) to rat liver DNA in vivo and of its N-hydroxylated derivative to DNA in vitro. Silk, N.A., Lay, J.O., Martin, C.N. Biochem. Pharmacol. (1989) [Pubmed]
  23. Determination of 4,4'-methylenebis(2-chloroaniline) in urine using capillary gas chromatography and negative ion chemical ionization mass spectrometry. Jedrzejczak, K., Gaind, V.S. The Analyst. (1992) [Pubmed]
  24. 4,4'-Methylene-bis(2-chloroaniline) (MOCA): comparison of macromolecular adduct formation after oral or dermal administration in the rat. Cheever, K.L., Richards, D.E., Weigel, W.W., Begley, K.B., DeBord, D.G., Swearengin, T.F., Savage, R.E. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1990) [Pubmed]
  25. 4,4'-Methylenebis(2-chloroaniline) (MOCA): the effect of multiple oral administration, route, and phenobarbital induction on macromolecular adduct formation in the rat. Cheever, K.L., DeBord, D.G., Swearengin, T.F. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1991) [Pubmed]
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