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

CHEBI:957     2-methyl-1,3-dinitro-benzene

Synonyms: SGCUT00101, CPD-9133, ACMC-1BBLJ, CCRIS 1006, AG-G-20067, ...
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 C11008


High impact information on C11008

  • HPLC with a water/acetonitrile gradient on a C-18 reversed-phase column was then used to determine these three compounds plus the four additional examples, 1,3,5,7-tetrazocine, 2,4-dinitrotoluene; 2,6-dinitrotoluene, and 4-nitrotoluene [5].
  • Based on previous initiation study results from our laboratory and the present data, 2,6-DNT appears to be a complete hepatocarcinogen while under the conditions of these studies 2,4-DNT is an apparent 'pure promoter'. These results provide an explanation for the conflicting DNT bioassay results [6].
  • These results establish that TDNT, 2,4-DNT and 2,6-DNT have hepatocyte foci promoting activity and that 2,6-DNT is approximately 10 times more potent than 2,4-DNT [6].
  • The MWs of one composite explosive composed of 2,6-DNT, TNT, and RDX, one propellant with unknown components, and 14 single-compound explosives (RDX, HMX, 3,4-DNT, 2,6-DNT, 2,5-DNT, 2,4,6-TNT, TNAZ, DNI, BTTN, NG, TO, NTO, NP, and 662) were measured [7].
  • Compared to the wild type, the F293Q mutant was 2.5 times faster at oxidizing 2,6-dinitrotoluene while retaining a similar Km for the substrate based on product formation rates and whole-cell kinetics [8].

Chemical compound and disease context of C11008

  • Definitive tests established that the order of EM toxicity to E. crypticus based on the median effect concentration values for juvenile production in either freshly amended or weathered and aged treatments was (from the greatest to least toxicity) TNB > 2,4-DNT > 2,6-DNT [9].
  • Weathering and aging of energetic materials (EMs) in soil significantly decreased the toxicity of TNT, TNB or 2,6-DNT to Japanese millet or ryegrass based on seedling emergence, but significantly increased the toxicity of all four EMs to all three plant species based on shoot growth [10].
  • Fate and effects of picric acid and 2,6-DNT in marine environments: toxicity of degradation products [11].

Biological context of C11008

  • The performance characteristics show that the method holds promise and reliable data may be obtained for 2,6-DNT in bioanalysis and public health [12].
  • However, regarding 2,6-DNT and TNB higher reduction rates than calculated were actually achieved by alkaline hydrolysis [13].
  • Hence, oxidation of 2,3-DNT, 2,4-DNT, 2,5-DNT, 2,6-DNT, 2NT, and 4NT were enhanced here by performing saturation mutagenesis on codon I204 of the alpha subunit (DntAc) of DDO and by using a membrane agar plate assay to detect catechol formation [14].
  • Comparative intestinal nitroreductase, azo reductase, beta-glucuronidase, dechlorinase and dehydrochlorinase activities in young male Fischer 344 rats and young male CD-1 mice were measured in vitro while the comparative biotransformation of 2,6-dinitrotoluene to mutagenic metabolites was determined in vivo [15].
  • Photo-transformation of 2,6-DNT in seawater resulted in a reduction in toxicity [11].

Anatomical context of C11008

  • The present studies were designed to determine the relative hepatocyte foci promoting activity of TDNT and the primary isomers present in the technical mixture, 2,4- and 2,6-DNT [6].
  • The enhanced genotoxicity observed in urines from 2,6-DNT/PCP-treated mice coincided with a decrease in nitroreductase and an increase in beta-glucuronidase activities in the small intestine [16].
  • These results indicate that xanthine oxidase contributes to the hypoxanthine-supported anaerobic metabolism of 2,6-DNT by human liver cytosol [17].
  • After male germ-free and conventionalized Fischer 344 rats were administered per os (p.o.) 75 mg/kg 2,6-DNT, intestinal nitroreductase, beta-glucuronidase, and azo reductase activities were lower in the cecum and large intestine of germ-free animals [18].
  • 1. 2,6-Dinitrotoluene (2,6-DNT) metabolism by human liver and male Fischer F344 rat liver subcellular fractions under aerobic (100% oxygen) and anaerobic (100% nitrogen) incubation conditions was examined [17].

Associations of C11008 with other chemical compounds


Analytical, diagnostic and therapeutic context of C11008

  • A single administration of either TDNT or 2,6-dinitrotoluene (75 mg/kg, p.o.), in combination with partial hepatectomy, initiated hepatocytes in rats when assayed using hepatic initiation-promotion protocols [21].
  • Two distinct hepatic DNA adducts (0.8+/-0.1 and 0.6+/-0.1 RAL/10(8) nucleotides) were detected in B6C3F1 mice by (32)P-postlabeling and thin layer chromatography which differed from the four adducts observed in hepatic DNA from 2,6-DNT-treated Fischer 344 rats [22].
  • Distribution, elimination, and test for carcinogenicity of 2,6-dinitrotoluene after intraperitoneal and oral administration to strain a mice [23].


  1. Dinitrotoluene isomer-specific hepatocarcinogenesis in F344 rats. Leonard, T.B., Graichen, M.E., Popp, J.A. J. Natl. Cancer Inst. (1987) [Pubmed]
  2. Aerobic degradation of dinitrotoluenes and pathway for bacterial degradation of 2,6-dinitrotoluene. Nishino, S.F., Paoli, G.C., Spain, J.C. Appl. Environ. Microbiol. (2000) [Pubmed]
  3. Construction of a Pseudomonas hybrid strain that mineralizes 2,4,6-trinitrotoluene. Duque, E., Haidour, A., Godoy, F., Ramos, J.L. J. Bacteriol. (1993) [Pubmed]
  4. Isomer- and sex-specific bioactivation of mononitrotoluenes. Role of enterohepatic circulation. Chism, J.P., Rickert, D.E. Drug Metab. Dispos. (1985) [Pubmed]
  5. Chromatographic detection of nitroaromatic and nitramine compounds by electrochemical reduction combined with photoluminescence following electron transfer. Woltman, S.J., Even, W.R., Sahlin, E., Weber, S.G. Anal. Chem. (2000) [Pubmed]
  6. Dinitrotoluene isomer-specific enhancement of the expression of diethylnitrosamine-initiated hepatocyte foci. Leonard, T.B., Adams, T., Popp, J.A. Carcinogenesis (1986) [Pubmed]
  7. Using molecular recognition of beta-cyclodextrin to determine molecular weights of low-molecular-weight explosives by MALDI-TOF mass spectrometry. Zhang, M., Shi, Z., Bai, Y., Gao, Y., Hu, R., Zhao, F. J. Am. Soc. Mass Spectrom. (2006) [Pubmed]
  8. Control of substrate specificity by active-site residues in nitrobenzene dioxygenase. Ju, K.S., Parales, R.E. Appl. Environ. Microbiol. (2006) [Pubmed]
  9. Toxicities of dinitrotoluenes and trinitrobenzene freshly amended or weathered and aged in a sandy loam soil to Enchytraeus crypticus. Kuperman, R.G., Checkai, R.T., Simini, M., Phillips, C.T., Kolakowski, J.E., Kurnas, C.W. Environ. Toxicol. Chem. (2006) [Pubmed]
  10. Phytotoxicity of nitroaromatic energetic compounds freshly amended or weathered and aged in sandy loam soil. Rocheleau, S., Kuperman, R.G., Martel, M., Paquet, L., Bardai, G., Wong, S., Sarrazin, M., Dodard, S., Gong, P., Hawari, J., Checkai, R.T., Sunahara, G.I. Chemosphere (2006) [Pubmed]
  11. Fate and effects of picric acid and 2,6-DNT in marine environments: toxicity of degradation products. Nipper, M., Carr, R.S., Biedenbach, J.M., Hooten, R.L., Miller, K. Mar. Pollut. Bull. (2005) [Pubmed]
  12. Development of an electrochemical assay for 2,6-dinitrotoluene, based on a screen-printed carbon electrode, and its potential application in bioanalysis, occupational and public health. Honeychurch, K.C., Hart, J.P., Pritchard, P.R., Hawkins, S.J., Ratcliffe, N.M. Biosensors & bioelectronics. (2003) [Pubmed]
  13. Kinetics of the alkaline hydrolysis of important nitroaromatic co-contaminants of 2,4,6-trinitrotoluene in highly contaminated soils. Emmrich, M. Environ. Sci. Technol. (2001) [Pubmed]
  14. Saturation mutagenesis of 2,4-DNT dioxygenase of Burkholderia sp. strain DNT for enhanced dinitrotoluene degradation. Leungsakul, T., Keenan, B.G., Yin, H., Smets, B.F., Wood, T.K. Biotechnol. Bioeng. (2005) [Pubmed]
  15. Comparative gastrointestinal enzyme activity and activation of the promutagen 2,6-dinitrotoluene in male CD-1 mice and male Fischer 344 rats. Chadwick, R.W., George, S.E., Chang, J., Kohan, M.J., Dekker, J.P., Long, J.E., Duffy, M.C. Cancer Lett. (1990) [Pubmed]
  16. Effect of pentachlorophenol on the activation of 2,6-dinitrotoluene to genotoxic urinary metabolites in CD-1 mice: a comparison of GI enzyme activities and urine mutagenicity. George, S.E., Chadwick, R.W., Creason, J.P., Kohan, M.J., Dekker, J.P. Environ. Mol. Mutagen. (1991) [Pubmed]
  17. Metabolism of 2,6-dinitro[3-3H]toluene by human and rat liver microsomal and cytosolic fractions. Chapman, D.E., Michener, S.R., Powis, G. Xenobiotica (1992) [Pubmed]
  18. Role of the intestinal microbiota in the activation of the promutagen 2,6-dinitrotoluene to mutagenic urine metabolites and comparison of GI enzyme activities in germ-free and conventionalized male Fischer 344 rats. George, S.E., Chadwick, R.W., Kohan, M.J., Allison, J.C., Williams, R.W., Chang, J. Cancer Lett. (1994) [Pubmed]
  19. Metabolism of 2,4-dinitrotoluene and 2,6-dinitrotoluene, and their dinitrobenzyl alcohols and dinitrobenzaldehydes by Wistar and Sprague-Dawley rat liver microsomal and cytosol fractions. Mori, M., Kawajiri, T., Sayama, M., Miyahara, T., Kozuka, H. Chem. Pharm. Bull. (1989) [Pubmed]
  20. Development of marine toxicity data for ordnance compounds. Nipper, M., Carr, R.S., Biedenbach, J.M., Hooten, R.L., Miller, K., Saepoff, S. Arch. Environ. Contam. Toxicol. (2001) [Pubmed]
  21. Dinitrotoluene structure-dependent initiation of hepatocytes in vivo. Leonard, T.B., Lyght, O., Popp, J.A. Carcinogenesis (1983) [Pubmed]
  22. Hepatic DNA adducts and production of mutagenic urine in 2,6-dinitrotoluene-treated B6C3F1 male mice. George, S.E., Kohan, M.J., Warren, S.H. Cancer Lett. (1996) [Pubmed]
  23. Distribution, elimination, and test for carcinogenicity of 2,6-dinitrotoluene after intraperitoneal and oral administration to strain a mice. Schut, H.A., Loeb, T.R., Grimes, L.A., Stoner, G.D. Journal of toxicology and environmental health. (1983) [Pubmed]
WikiGenes - Universities