Trinitrotoluene (TNT), or more specifically, 2,4,6-trinitrotoluene, is a chemical compound with the formula C6H2(NO2)3CH3. This yellow-coloured solid is a reagent (reactant) in chemistry but is best known as a useful explosive material with convenient handling properties. The explosive yield of TNT is considered the standard measure of strength of bombs and other explosives. In chemistry, TNT is used to generate charge transfer salts. (3)
belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
2,4,6-Trinitrotoluene is a competitive inhibitor with respect to NADPH and a noncompetitive inhibitor with respect to L-arginine. It binds to the P450 reductase domain of the eNOS and suppresses l-citrulline formation by shunting electrons away from the normal catalytic pathway. The reduction of TNT then produces reactive oxygen species (ROS), such as superoxide (O2.−), and hydrogen peroxide (H2O2). The overproduction of superoxide is associated with oxidative stress-mediated induction of cataracts. The inhibition of the eNOS activity occurs in a concentration-dependent manner. (1, 2)
Metabolism
2,4,6-Trinitrotoluene rapidly and completely enters the body through inhalation or ingestion, but more slowly through the skin. Once 2,4,6-trinitrotoluene is in the blood, it travels throughout the body to all of the organs. When it reaches the liver, it breaks down and changes into several different substances, such as 4-aminodinitrotoluene, 2-aminodinitrotoluene and 2,4-diamino-6-nitrotoluene. Most of these substances travel in the blood until they reach the kidneys. Almost all of the 2,4,6-trinitrotoluene that enters the body breaks down and leaves the body in the urine within 24 hours. (5)
3, not classifiable as to its carcinogenicity to humans. (7)
Uses/Sources
2,4,6-Trinitrotoluene is an explosive used in military shells, bombs, and grenades, in industrial uses, and in underwater blasting. Exposure may results from drinking contaminated water that has migrated from chemical waste disposal sites, breathing contaminated air, eating contaminated foods such as fruits and vegetables, and/or eating contaminated soil. (5)
Exposition to high concentrations of 2,4,6-trinitrotoluene in air can lead to several harmful health effects, including anemia and abnormal liver function. Similar blood and liver effects, as well as spleen enlargement and other harmful effects on the immune system, have been observed in animals that ate or breathed 2,4,6-trinitrotoluene. Other effects in humans include skin irritation after prolonged skin contact, and cataract development after long-term (365 days or longer) exposure. It is not known whether 2,4,6-trinitrotoluene can cause birth defects in humans. However, male animals treated with high doses of 2,4,6-trinitrotoluene have developed serious reproductive system effects. Moreover, the EPA has determined that 2,4,6-trinitrotoluene is a possible human carcinogen. (5)
Symptoms
Exposure to 2,4,6-trinitrotoluene causes headache, blue lips or finger nails, blue skin, cough, sore throat, laboured breathing, vomiting, abdominal cramps, unconsciousness. Dermal exposure may cause pain and redness at the exposed surface and yellowish staining of the skin. (4)
Treatment
In some cases, gastric lavage, activated charcoal, and emetics have been suggested as useful in reducing absorption of the general class of nitro compounds to which 2,4,6-trinitrotoluene belongs. (5)
Hubert E. de Cazenove, Daniel Doyen, Jacques M. Dussidour, Jean-Jacques Gautier, “Process for continuous production of trinitrotoluene.” U.S. Patent US4022844, issued May, 1960.
