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Name Description
id 73
T3DB ID T3D0082
Name 2,4,6-Trinitrotoluene
Class SmallMolecule
Description 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. (L130)
Categories "Industrial/Workplace Toxin", "Food Toxin", "Synthetic Toxin"
Types "Organic Compound", "Aromatic Hydrocarbon", "Indicator and Reagent", "Explosive Agent", "Nitrite", "Food Toxin", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "1-Methyl-2,4,6-trinitrobenzene", "2,4,6-TNT", "2,4,6-Trinitrotoluol", "s-Trinitrotoluol", "sym-Trinitrotoluol", "TNT", "Trinitrotoluene", "Trinitrotoluol", "Tritol", "Trotyl"
CAS Number 118-96-7
Chemical Formula C7H5N3O6
Average Molecular Mass 227.13
Monoisotopic Mass 227.02
IUPAC Name 2-methyl-1,3,5-trinitrobenzene
Traditional Name ?-tnt
SMILES CC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
InChI Identifier InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3
InChI Key InChIKey=SPSSULHKWOKEEL-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Toluenes
Direct Parent Nitrobenzenes
Alternate Parents "Nitrobenzenes", "Nitro Compounds", "Nitronic Acids", "Propargyl-Type 1,3-Dipolar Organic Compounds", "Organic Oxoazanium Compounds", "Organonitrogen Compounds", "Organic Salts", "Organic Zwitterions"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "organonitrogen compound", "nitronic acid", "nitro compound", "organic oxoazanium", "nitrobenzene", "Aromatic Homomonocyclic Compound", "Propargyl-Type 1,3-Dipolar Organic Compound", "Organic 1,3-Dipolar Compound", "Allyl-Type 1,3-Dipolar Organic Compound", "Organic Salt", "Organic Zwitterion", "Dinitrotoluene"
Descriptors "an aromatic compound (MetaCyc)", "trinitrotoluene (ChEBI)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Solid
Appearance Pale yellow, odorless solid. Loose "needles" before melt-casting. A solid block after being poured into a casing. (L130)
Melting Point 80.1°C
Boiling Point 240 °C (L131)
Solubility 0.115 mg/mL at 23 °C [PHELAN,JM & BARNETT,JL (2001)]
LogP
Route of Exposure Oral (L131) ; inhalation (L131) ; dermal (L131)
Mechanism of Toxicity 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. (A110, A111)
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. (L132)
Toxicity
Lethal Dose
Carcinogenicity 3, not classifiable as to its carcinogenicity to humans. (L135)
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. (L132)
Minimum Risk Level Intermediate Oral: 0.0005 mg/kg/day (L134)
Health Effects 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. (L132)
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. (L131)
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. (L132)
DrugBank ID DB01676
HMDB ID
PubChem Compound ID 8376
ChEMBL ID CHEMBL1236345
ChemSpider ID 8073
KEGG Compound ID C16391
UniProt ID 0
OMIM ID 0
ChEBI ID 46053
BioCyc ID CPD-9138
CTD ID D014303
Stitch ID 2,4,6-Trinitrotoluene
PDB ID
ACToR ID 6562
Wikipedia Link http://en.wikipedia.org/wiki/Trinitrotoluene
Creation Date 2009-03-06 18:58:02
Update Date 2014-12-24 20:21:04