4714 2-Chlorobenzylidene malononitrile The compound 2-chlorobenzylidene malononitrile (also called o-chlorobenzylidene malononitrile) (chemical formula: C10H5ClN2), acyanocarbon, is the defining component of a tear gas commonly referred to as CS gas, which is used as a riot control agent. CS gas is an aerosol of avolatile solvent (a substance that dissolves other active substances and that easily evaporates) and 2-chlorobenzalmalononitrile, which is a solid compound at room temperature. 2698-41-1 17604 C10H5ClN2 White powder. 93°C (199.4°F) 310°C (590°F) Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97) Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96) No indication of carcinogenicity to humans (not listed by IARC). 2-Chlorobenzylidene malononitrile can cause severe pulmonary damage and damage of the heart and liver. Symptoms include eye irritation, tearing, burning sensation on the nose and throat, rhinorrhoea, excess salivation, constricting sensations in the chest, sneezing, coughing, and stinging or burning sensations in exposed skin. 2014-09-08T02:41:34Z 2026-04-03T08:01:42Z http://en.wikipedia.org/wiki/CS_gas true [H]C(=C(C#N)C#N)C1=C([H])C([H])=C([H])C([H])=C1Cl C10H5ClN2 InChI=1S/C10H5ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-5H JJNZXLAFIPKXIG-UHFFFAOYSA-N 188.613 188.014125877 Exogenous Solid CHEMBL1256101 16644 CHEM003618 DTXSID9020297 2-[(2-chlorophenyl)methylidene]propanedinitrile