Toxicity of nitrobenzene

The toxicity of nitrobenzene consists primarily in the formation of methaemo-globine in the blood. It is also toxic for the nervous system and the liver. At concentrations in air exceeding 5 mg/m3 it is considered dangerous. Poisoning by nitrobenzene may be caused either by its direct contact with the skin or when it is inhaled as vapour. Symptoms of slight poisoning include nausea, headache, 

---

Yuan, X. and Lang, P. QSAR study of the toxicity of nitrobenzenes to river bacteria and Photobacteriumphosphoreum. Bull... 

The reduction of nitro groups may also be catalyzed by microsomal reductases and gut bacterial enzymes. The reduction passes through several stages to yield the fully reduced primary amine, as illustrated for nitrobenzene (Fig. 4.39). The intermediates are nitrosobenzene and phenylhydroxylamine, which are also reduced in the microsomal system. These intermediates, which may also be produced by the oxidation of aromatic amines (Fig. 4.21), are involved in the toxicity of nitrobenzene to red blood cells after oral administration to rats. The importance of the gut bacterial reductases in this process is illustrated by the drastic reduction in nitrobenzene toxicity in animals devoid of gut bacteria, or when nitrobenzene is given by the intraperitoneal route. 

These studies indicate that intestinal microfloral metabolism and red blood cell toxicity of nitrobenzene is markedly different in animals fed cereal-based versus purified diets. Furthermore, since inclusion of pectin into the purified diet diminishes the magnitude of these effects, differences in dietary composition of fermentable carbohydrates in cereal-based and purified diets may mediate differences in metabolism and toxicity of nitrobenzene (27). 

Altenburger R, Schmitt H, Schuurmann G. 2005. Algal toxicity of nitrobenzenes combined effect analysis as a pharmacological probe for similar modes of interaction. Environ Toxicol Chem 24 324-333. 

Purdy, R., Quantitative structure-activity relationships for predicting toxicity of nitrobenzenes, phenols, anilines, and alkylamines to fathead minnows, in QSAR 88. Proceedings of the Third International Workshop on Quantitative Structure-Activity Relationships in Environmental Toxicology, Turner, J.E., England, M.W., Schultz, T.W., and Kwaak, N.J., Eds., National Technical Information Service, U.S. Department of Commerce, Springfield, VA, 1988, pp. 99-110. 

Gough, K.M., Belohorcova, K. and Kaiser, K.L. (1994). Quantitative Structure-Activity Relationships (QSARs) of Photobacterium Phosphoreum Toxicity of Nitrobenzene Derivatives. ScLTotal Environ., 142,179-190. 

Bohac, M., Loeprecht, B., Damborsky, J. and Schiiiirmann, G. (2002) Impact of orthogonal signal correction (OSC) on the predictive ability of CoMFA models for the dilate toxicity of nitrobenzenes. Quant. Struct. -Act. Relat., 21, 3-11. 

Shrivastava, S., Jaiswal, M., Gutman, 1., Karmarkar, S. and Shrivastava, A. (2003) Equalized electronegativity and topological indices application for modeling toxicity of nitrobenzene derivatives. Indian J. Chem., 42, 1436-1441. 

Roy, K. and Ghosh, G. (2004b) QSTR with extended topochemical atom indices. 3. Toxicity of nitrobenzenes to Tetrahymena pyriformis. QSAR Comb. Sci., 23, 99-108. 

Schiiiirmann, G., Elemmig, B. and Dearden, J.C. (1997) CoMEA study of acute toxicity of nitrobenzenes to Tetrahymena pyriformis, in Quantitative Structure—Activity Relationships in Environmental Sciences — VII (eds E. Chen and G. Schiiiirmann), SETAC Press, Pensacola, PL, pp. 315-327. 

Alcohol also has the potential for enhancing the toxicity of nitrobenzene however the toxicokinetic mechanism is not known. It is clear, however, that alcohol does not simply enhance the absorption of nitrobenzene. When alcohol was given orally and nitrobenzene is given intravenously, there was increased toxicity in rabbits. Alcohol also enhanced the neural toxicity of nitrobenzene in rabbits when nitrobenzene was applied to the skin (Matsumaru and Yoshida 1959). 

Bio/dynamics Inc. 1983. A range-finding study to evaluate the toxicity of nitrobenzene in the pregnant rabbit. Final Report. East Millstone, NJ Bio/dynamics Inc. Project Report 83-2723. 

Donovan WM. 1920. The toxicity of nitrobenzene with report of a fatal case. JAMA 74 1647. 

Goldstein RS, Chism JP, Sherrill JM, et al. 1984a. Influence of dietary pectin on intestinal microfloral metabolism and toxicity of nitrobenzene. Toxicol Appl Pharmacal 75 547-553. 

Irons RD, Hamm TE Jr, Rickert DE. 1985. Effect of dietary pectin on the target organ toxicity of nitrobenzene (NB) [Abstract], Toxicologist 5 91. 

Deneer J et al., QS AR study of the toxicity of nitrobenzene derivatives towards Daphnia magna, Chlorella pyrenoidosa and Photobacterium phosphoreum, Aquat. Toxicol., 15, 83, 1989. 

O Brien PJ et al., Toxicity of nitrobenzene compounds towards isolated hepatocytes Dependence on reduction potential, Xenobiotica, 20, 945, 1990. 

TABLE 4.1 Toxicity of Nitrobenzenes and Derivatives TABLE 4.2 Toxicity of Nitrotoluenes... 

Nitrobenzene Physical properties Chemical properties Toxicity of nitrobenzene Preparation of nitrobenzene Diniirobenzcnes Physical properties Chemical properties Toxicity of dinitrohenzenes Explosive properties of diniirobenzene Sensitivity to impact Preparation of dinitrohenzenes Nitration in two stages in two niirators Purification... 

Roberts, D.W. 1987. An analysis of published data on fish toxicity of nitrobenzene and aniline derivatives. In QSAR in Environmental Toxicology - II, Kaiser, K.L.E. (Ed.), D. Reidel Publ. Co., Dordrecht, Holland, pp. 295-308. 

AN ANALYSIS OF PUBLISHED DATA ON FISH TOXICITY OF NITROBENZENE AND ANILINE DERIVATIVES... 

---