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Chemical Compound Review:

PubChem12509 2,2-dibromoethanenitrile

Synonyms: CCRIS 2673, AG-F-08767, ACMC-20alau, HSDB 6862, LS-1196, ...

Fu, L.J. et al., Nikolaou, A.D. et al., Lin, E.L. et al., Hayes, J.R. et al., Ahmed, A.E. et al., et al.

Nikolaou, Golfinopoulos, Kostopoulou, Lekkas,

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 DIBROMOACETONITRILE

In the Ames-fluctuation test, all the compounds except dibromoacetonitrile showed mutagenic activity on Salmonella typhimurium strain TA100 [1].
The subchronic toxicity of dibromoacetonitrile (DBAN), a disinfection by-product in drinking water, was studied in the rat [2].

High impact information on DIBROMOACETONITRILE

DCAN reacted with polyadenylic acid and DNA to form adducts in a cell-free system; however, the oral administration of DBAN or DCAN to rats did not result in detectable adduct formation in liver DNA [3].
The acute oral LD50 values (mg/kg) in mice and rats are: DBAN, mice: 289 (M), 303 (F); DBAN, rats: 245 (M), 361 (F); DCAN, mice: 270 (M), 279 (F); DCAN, rats: 339 (M), 330 (F) [4].
In this report we show that dichloroacetonitrile, but not dibromoacetonitrile, is an effective inducer of aneuploidy in oocytes of Drosophila melanogaster [5].
Neurotoxicological evaluation of two disinfection by-products, bromodichloromethane and dibromoacetonitrile, in rats [6].
In vitro activation of dibromoacetonitrile to cyanide: role of xanthine oxidase [7].

Chemical compound and disease context of DIBROMOACETONITRILE

For six of the chemicals tested by this assay (dibromoacetonitrile; trichloroacetonitrile; 2-chlorophenol; 2,4,6-trichlorophenol; trichloroacetic acid; dichloroacetone) it was predicted that they would be generally equally toxic to both adult and embryonic mammals when studied by means of standard developmental toxicity "teratology" tests [8].
Studies on the mechanism of haloacetonitrile-induced gastrointestinal toxicity: interaction of dibromoacetonitrile with glutathione and glutathione-S-transferase in rats [9].
Testicular toxicity of dibromoacetonitrile and possible protection by tertiary butylhydroquinone [10].

Biological context of DIBROMOACETONITRILE

Dibromoacetonitrile (DBAN) is a disinfection byproduct of chlorination of drinking water [7].

Associations of DIBROMOACETONITRILE with other chemical compounds

The concentrations of dichloroacetonitrile (CHCl2CN, DCAN), bromochloroacetonitrile (CHBrClCN, BCAN) and dibromoacetonitrile (CHBr2CN, DBAN) were determined by a gas chromatography mass spectrometry (GC-MS) method at regular time intervals and different temperatures [11].

References

Study of the genotoxic activity of six halogenated acetonitriles, using the SOS chromotest, the Ames-fluctuation test and the newt micronucleus test. Le Curieux, F., Giller, S., Gauthier, L., Erb, F., Marzin, D. Mutat. Res. (1995) [Pubmed]
Effects of dibromoacetonitrile on rats following 13-week drinking water exposure. Poon, R., Chu, I., LeBel, G., Yagminas, A., Valli, V.E. Food Chem. Toxicol. (2003) [Pubmed]
Haloacetonitriles: metabolism, genotoxicity, and tumor-initiating activity. Lin, E.L., Daniel, F.B., Herren-Freund, S.L., Pereira, M.A. Environ. Health Perspect. (1986) [Pubmed]
Toxicology of haloacetonitriles. Hayes, J.R., Condie, L.W., Borzelleca, J.F. Environ. Health Perspect. (1986) [Pubmed]
Dichloroacetonitrile, a by-product of water chlorination, induces aneuploidy in Drosophila. Osgood, C., Sterling, D. Mutat. Res. (1991) [Pubmed]
Neurotoxicological evaluation of two disinfection by-products, bromodichloromethane and dibromoacetonitrile, in rats. Moser, V.C., Phillips, P.M., McDaniel, K.L., Sills, R.C. Toxicology (2007) [Pubmed]
In vitro activation of dibromoacetonitrile to cyanide: role of xanthine oxidase. Mohamadin, A.M., Abdel-Naim, A.B. Arch. Toxicol. (2003) [Pubmed]
Prediction of the developmental toxicity hazard potential of halogenated drinking water disinfection by-products tested by the in vitro hydra assay. Fu, L.J., Johnson, E.M., Newman, L.M. Regulatory toxicology and pharmacology : RTP. (1990) [Pubmed]
Studies on the mechanism of haloacetonitrile-induced gastrointestinal toxicity: interaction of dibromoacetonitrile with glutathione and glutathione-S-transferase in rats. Ahmed, A.E., Hussein, G.I., Loh, J.P., Abdel-Rahman, S.Z. J. Biochem. Toxicol. (1991) [Pubmed]
Testicular toxicity of dibromoacetonitrile and possible protection by tertiary butylhydroquinone. Abdel-Wahab, M.H. Pharmacol. Res. (2003) [Pubmed]
Decomposition of dihaloacetonitriles in water solutions and fortified drinking water samples. Nikolaou, A.D., Golfinopoulos, S.K., Kostopoulou, M.N., Lekkas, T.D. Chemosphere (2000) [Pubmed]

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