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Chemical Compound Review

TOLUIDINE     2-methylaniline

Synonyms: o-Toluidin, o-Toluidine, o-Toluidyna, o-Tolylamine, o-Aminotoluene, ...
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Disease relevance of HSDB 2042

  • Norharman (9H-pyrido[3,4-b]indole), widely distributed in our environment, including cigarette smoke and cooked foodstuffs, is not mutagenic to Salmonella strains, but becomes mutagenic to S.typhimurium TA98 and YG1024 with S9 mix in the presence of non-mutagenic aromatic amines such as aniline and o-toluidine [1].
  • Advantages of this reagent over o-toluidine include lower cost, less toxicity, and higher purity [2].
  • PolyP was detected in KcsA tetramers, but not in monomers, by metachromatic reaction to o-toluidine blue stain on SDS-PAGE gels [3].
  • Acinetobacter sp. strain YAA is able to use aniline and o-toluidine as the sole carbon and energy source [4].
  • EMLA (eutectic mixture of lidocaine and prilocaine) cream is currently not recommended for use in infants < 1 month of age because of the potential risk of methemoglobinemia as a result of the o-toluidine metabolite of prilocaine [5].

High impact information on HSDB 2042

  • These data support the conclusion that occupational exposure to o-toluidine is the most likely causal agent of the bladder cancer excess observed among workers in the rubber chemicals department of the plant under study, although exposures to aniline and 4-ABP cannot be ruled out [6].
  • PURPOSE: An environmental and biological monitoring survey was conducted to evaluate current exposures to aniline and o-toluidine in the rubber chemicals department [6].
  • Smokers excreted 3.1 +/- 2.6 micrograms/24 h of aniline and 6.3 +/- 3.7 micrograms/24 h of o-toluidine (n = 16) [7].
  • This study reveals why human NAT1 acetylates the sunscreen additive p-aminobenzoic acid and tobacco smoke carcinogen 4-aminobiphenyl, but not o-toluidine and other arylamines linked to bladder cancer [8].
  • On the other hand, mononuclear compounds, such as benzene metabolites, caffeic acid, and o-toluidine, should express their carcionogenicity through oxidative DNA damage [9].

Chemical compound and disease context of HSDB 2042

  • Harman (1-methyl-9H-pyrido[3,4-b]indole) reacted readily with sodium hypochlorite in an aqueous medium to give the mono-chlorinated derivatives, which reportedly have greater co-mutagenic activity than harman in the presence of o-toluidine toward Salmonella typhimurium TA 98 with S9 mix [10].
  • Degradation of 2-methylaniline in Rhodococcus rhodochrous: cloning and expression of two clustered catechol 2,3-dioxygenase genes from strain CTM [11].
  • Rhodococcus rhodochrous strain CTM co-metabolized 2-methylaniline and some of its chlorinated isomers in the presence of ethanol as additional carbon source [12].

Biological context of HSDB 2042


Anatomical context of HSDB 2042


Associations of HSDB 2042 with other chemical compounds


Gene context of HSDB 2042

  • Results by the technique correlate reasonably with those by the o-toluidine and the hexokinase/glucose-6-phosphate dehydrogenase methods: Other sugars--including fructose, glucosamine, and mannose--will interfere; galactose does not [25].
  • After these procedures, the mixture was filtered through a MACS column and the staining with o-toluidine was repeated [20].
  • NIR vibrational overtone spectra of toluidines-evidence for steric and electronic effects in o-toluidine [26].
  • Ab initio calculations at MP2/6-31 + G* and CIS/6-31 + G* show that the optimised structure of o-methylaniline in the ground state is not planar with the amino group having sp3 hybridation-like character due to the existence of lone paired electrons on the N atom [16].
  • In-situ spectroelectrochemical studies on the copolymerization of o-toluidine (OT) with diphenylamine-4-sulfonic acid (DPASA) were carried out on ITO electrode in 0.5 M H2SO4 for different feed ratios of OT and DPASA [27].

Analytical, diagnostic and therapeutic context of HSDB 2042

  • A retrospective cohort study of the incidence of bladder cancer was conducted in response to a union request for an evaluation of a possible excess number of cases of bladder cancer at a chemical plant in western New York State. Workers at the plant were exposed to two potential bladder carcinogens--ortho-toluidine (o-toluidine) and aniline [28].
  • After mild base treatment of Hb, 2-methylaniline (2MA) was released and quantified using gas chromatography/mass spectrometry [29].
  • When norharman and o-toluidine were reacted at 37 degrees C for 20 min, two mutagenic compounds, which were mutagenic with and without S9 mix, respectively, were produced, and these were isolated by HPLC [30].
  • The o-toluidine high-performance thin-layer chromatography (HPTLC) method for detection of reducing sugars has been demonstrated to be a facile method for composition analysis of protein hydrolysates with a maximum sensitivity range of 50-100 pmol [31].
  • Our results reveal that the QCOB test has significantly higher positive rates of fecal occult blood than either the OC-Hemodia test or o-toluidine test [32].


  1. Structural determination of a mutagenic aminophenylnorharman produced by the co-mutagen norharman with aniline. Totsuka, Y., Hada, N., Matsumoto, K., Kawahara, N., Murakami, Y., Yokoyama, Y., Sugimura, T., Wakabayashi, K. Carcinogenesis (1998) [Pubmed]
  2. P-Hydroxybenzoic acid hydrazide procedure for serum glucose adapted to the Technicon "SMA 12/60," and compared with other glucose methods. Ferraro, J.J., Caccavo, F.A., Saifer, A. Clin. Chem. (1976) [Pubmed]
  3. Streptomyces lividans potassium channel contains poly-(R)-3-hydroxybutyrate and inorganic polyphosphate. Reusch, R.N. Biochemistry (1999) [Pubmed]
  4. Plasmid-encoded genes specifying aniline oxidation from Acinetobacter sp. strain YAA. Fujii, T., Takeo, M., Maeda, Y. Microbiology (Reading, Engl.) (1997) [Pubmed]
  5. Penile absorption of EMLA cream in piglets: implications for use of EMLA in neonatal circumcision. Gazarian, M., Taddio, A., Klein, J., Kent, G., Koren, G. Biol. Neonate (1995) [Pubmed]
  6. Monitoring of aromatic amine exposures in workers at a chemical plant with a known bladder cancer excess. Ward, E.M., Sabbioni, G., DeBord, D.G., Teass, A.W., Brown, K.K., Talaska, G.G., Roberts, D.R., Ruder, A.M., Streicher, R.P. J. Natl. Cancer Inst. (1996) [Pubmed]
  7. Identification and quantitative determination of aniline and toluidines in human urine. el-Bayoumy, K., Donahue, J.M., Hecht, S.S., Hoffmann, D. Cancer Res. (1986) [Pubmed]
  8. NMR-based Model Reveals the Structural Determinants of Mammalian Arylamine N-Acetyltransferase Substrate Specificity. Zhang, N., Liu, L., Liu, F., Wagner, C.R., Hanna, P.E., Walters, K.J. J. Mol. Biol. (2006) [Pubmed]
  9. The role of metals in site-specific DNA damage with reference to carcinogenesis. Kawanishi, S., Hiraku, Y., Murata, M., Oikawa, S. Free Radic. Biol. Med. (2002) [Pubmed]
  10. Identification of co-mutagenic chlorinated harmans in final effluent from a sewage treatment plant. Fukazawa, H., Matsushita, H., Terao, Y. Mutat. Res. (2001) [Pubmed]
  11. Degradation of 2-methylaniline in Rhodococcus rhodochrous: cloning and expression of two clustered catechol 2,3-dioxygenase genes from strain CTM. Schreiner, A., Fuchs, K., Lottspeich, F., Poth, H., Lingens, F. J. Gen. Microbiol. (1991) [Pubmed]
  12. Degradation of 2-methylaniline and chlorinated isomers of 2-methylaniline by Rhodococcus rhodochrous strain CTM. Fuchs, K., Schreiner, A., Lingens, F. J. Gen. Microbiol. (1991) [Pubmed]
  13. Induction of xenobiotic biotransformation by the insecticide chlordimeform, a metabolite 4-chloro-o-toluidine and a structurally related chemical o-toluidine. Leslie, C., Reidy, G.F., Murray, M., Stacey, N.H. Biochem. Pharmacol. (1988) [Pubmed]
  14. Metabolism of o-[methyl-14C]toluidine in the F344 rat. Son, O.S., Everett, D.W., Fiala, E.S. Xenobiotica (1980) [Pubmed]
  15. Correlation between induction of DNA fragmentation in urinary bladder cells from rats and humans and tissue-specific carcinogenic activity. Robbiano, L., Carrozzino, R., Bacigalupo, M., Corbu, C., Brambilla, G. Toxicology (2002) [Pubmed]
  16. A reinvestigation of the molecular structures, vibrations and rotation of methyl group in o-methylaniline in S0 and S1 states studied by laser induced fluorescence spectroscopy and ab initio calculations. Ballesteros, B., Santos, L. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2002) [Pubmed]
  17. Subacute toxicity of several ring-substituted dialkylanilines in the rat. Short, C.R., King, C., Sistrunk, P.W., Kerr, K.M. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1983) [Pubmed]
  18. Detection of monocyclic aromatic amines, possible mammary carcinogens, in human milk. DeBruin, L.S., Pawliszyn, J.B., Josephy, P.D. Chem. Res. Toxicol. (1999) [Pubmed]
  19. Evaluation of liver and peripheral blood micronucleus assays with 9 chemicals using young rats. A study by the Collaborative Study Group for the Micronucleus Test (CSGMT)/Japanese Environmental Mutagen Society (JEMS)-Mammalian Mutagenicity Study Group (MMS). Suzuki, H., Ikeda, N., Kobayashi, K., Terashima, Y., Shimada, Y., Suzuki, T., Hagiwara, T., Hatakeyama, S., Nagaoka, K., Yoshida, J., Saito, Y., Tanaka, J., Hayashi, M. Mutat. Res. (2005) [Pubmed]
  20. Reactive oxygen species in human semen: investigations and measurements. Hipler, U.C., Schreiber, G., Wollina, U. Arch. Androl. (1998) [Pubmed]
  21. Distinct heme-substrate interactions of lactoperoxidase probed by resonance Raman spectroscopy: difference between animal and plant peroxidases. Kitagawa, T., Hashimoto, S., Teraoka, J., Nakamura, S., Yajima, H., Hosoya, T. Biochemistry (1983) [Pubmed]
  22. The in vitro micronucleus test on isolated human lymphocytes. Vian, L., Bichet, N., Gouy, D. Mutat. Res. (1993) [Pubmed]
  23. Distinct mechanisms of oxidative DNA damage by two metabolites of carcinogenic o-toluidine. Ohkuma, Y., Hiraku, Y., Oikawa, S., Yamashita, N., Murata, M., Kawanishi, S. Arch. Biochem. Biophys. (1999) [Pubmed]
  24. Hemoglobin adducts of the human bladder carcinogen o-toluidine after treatment with the local anesthetic prilocaine. Gaber, K., Harr??us, U.A., Matthias, C., Kleinsasser, N.H., Richter, E. Toxicology (2007) [Pubmed]
  25. An immobilized-enzyme flow-enthalpimetric analyzer: application to glucose determination by direct phosphorylation catalyzed by hexokinase. Bowers, L.D., Carr, P.W. Clin. Chem. (1976) [Pubmed]
  26. NIR vibrational overtone spectra of toluidines-evidence for steric and electronic effects in o-toluidine. Shaji, S., Eappen, S.M., Nair, K.P., Rasheed, T.M. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2004) [Pubmed]
  27. In-situ spectroelectrochemical evidences for the copolymerization of o-toluidine with diphenylamine-4-sulphonic acid by UV-visible spectroscopy. Wen, T.C., Sivakumar, C., Gopalan, A. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2002) [Pubmed]
  28. Excess number of bladder cancers in workers exposed to ortho-toluidine and aniline. Ward, E., Carpenter, A., Markowitz, S., Roberts, D., Halperin, W. J. Natl. Cancer Inst. (1991) [Pubmed]
  29. Hemoglobin and DNA adducts in rats exposed to 2-nitrotoluene. Jones, C.R., Beyerbach, A., Seffner, W., Sabbioni, G. Carcinogenesis (2003) [Pubmed]
  30. Structures of mutagens produced by the co-mutagen norharman with o- and m-toluidine isomers. Hada, N., Totsuka, Y., Enya, T., Tsurumaki, K., Nakazawa, M., Kawahara, N., Murakami, Y., Yokoyama, Y., Sugimura, T., Wakabayashi, K. Mutat. Res. (2001) [Pubmed]
  31. An o-toluidine method for detection of carbohydrates in protein hydrolysates. Morcol, T., Velander, W.H. Anal. Biochem. (1991) [Pubmed]
  32. A comparative study of three fecal occult blood tests in upper gastrointestinal bleeding. Chiang, C.H., Jeng, J.E., Wang, W.M., Jheng, B.H., Hsu, W.T., Chen, B.H. Kaohsiung J. Med. Sci. (2006) [Pubmed]
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