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Name Description
id 83
T3DB ID T3D0094
Name 2,4-Dinitrotoluene
Class SmallMolecule
Description 2,4-Dinitrotoluene is the most common of the six dinitrotoluene isomers. Dinitrotoluene (DNT) or Dinitro is an explosive with the formula C6H3(CH3)(NO2)2. At room temperature it is a pale yellow to orange crystalline solid. It is a high explosive and one of the precursors for trinitrotoluene (TNT), which is synthesized through three separate nitrations of toluene. The first product is mononitrotoluene, DNT is the second, and TNT is the third and final product. (L270)
Categories "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Industrial Precursor/Intermediate", "Plasticizer", "Aromatic Hydrocarbon", "Explosive Agent", "Nitrite", "Pollutant", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "1-Methyl-2,4-dinitrobenzene", "2,4-Dinitro-1-methylbenzene", "2,4-Dinitromethylbenzene", "2,4-Dinitrotoluol", "2,4-DNT", "4-Methyl-1,3-dinitrobenzene", "DNT"
CAS Number 121-14-2
Chemical Formula C7H6N2O4
Average Molecular Mass 182.13
Monoisotopic Mass 182.03
IUPAC Name 1-methyl-2,4-dinitrobenzene
Traditional Name 2,4-dinitrotoluene
SMILES CC1=C(C=C(C=C1)N(=O)=O)N(=O)=O
InChI Identifier InChI=1S/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3
InChI Key InChIKey=RMBFBMJGBANMMK-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", "Organic Oxoazanium Compounds", "Propargyl-Type 1,3-Dipolar Organic Compounds", "Organic Salts", "Organonitrogen Compounds", "Organic Cations"
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 Cation", "Dinitrotoluene"
Descriptors "an aromatic compound (MetaCyc)", "dinitrotoluene (ChEBI)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Cell junction", "Cytosol", "Endoplasmic reticulum", "Extracellular", "Membrane", "Membrane Fraction", "Microsome", "Mitochondrion"
Biofluids
Tissues
Pathways "Apoptosis", "Oxidative phosphorylation", "Naphthalene Degradation", "Degradation Of Aromatic Compounds", "Caffeine Metabolism"
State Solid
Appearance At room temperature it is a pale yellow to orange crystalline solid. (L1151)
Melting Point 71°C
Boiling Point 250-300°C (decomposes)
Solubility 0.2 mg/mL at 25 °C [PHELAN,JM & BARNETT,JL (2001)]; 0.27 mg/mL at 22 °C [SEIDELL,A (1941)]
LogP
Route of Exposure Dermal (T44) ; eye contact (T44) ; inhalation (T44) ; oral (T44)
Mechanism of Toxicity 2,4-DNT may cause conversion of oxyhemoglobin to methemoglobin via oxidation of iron(II) to iron(III) by its metabolites. High levels of methemoglobin are removed by catabolism, leading to the development of anemia. Some metabolites of 2,4-DNT are also transported back from the bile to the liver, where the amine group is N-hydroxylated by cytochrome P-450 to form an unstable sulfate conjugate. The sulfate conjugate is degraded into carbonium or nitrenium ions. These ions covalently bind to hepatic macromolecules (DNA, RNA), leading to mutations and subsequently liver tumors. They also bind to DNA of the lung and the intestine. (L276, T45, A171, L280)
Metabolism 2,4-Dinitrotoluene can be inhalated as fumes or dust, ingested, or absorbed after contact with the skin. Bioactivation of 2,4-DNT is thought to occur by the following processes: The methyl group is oxidized to an alcohol by a cytochrome P-450 dependent pathway; the benzyl alcohol is conjugated with glucuronic acid and excreted in the bile. Intestinal microflora hydrolyzes the glucuronide and reduces one nitro group, forming an aminonitrobenzyl alcohol which can be readsorbed from the intestine. The amino group is oxidized to an hydroxylamine by hepatic enzymes and conjugated with sulfate, by sulfotransferase. Decomposition of the sulfate ester yields a highly electrophilic nitrenium (or carbonium) ion which can react with DNA and other biological nucleophiles. The major metabolite found in human urine is 2,4-dinitrobenzyl alcohol or its glucuronide conjugate. Other urinary metabolites include 2,4-dinitrobenzoic acid, 4-(N-acetyl)amino-2nitrobenzoic acid, and 2-amino-4-nitrobenzoic acid. The latter two are clearly the product of both oxidative and reductive metabolism. Metabolism is also believed to involve O-acetyltransferase (which transfers the acetyl group of 2,4-DNT) and cytosolic xanthine oxidase (which reduces 2,4-DNT). Small traces of unmetabolized 2,4-DNT can be observed in the urine too. (L276, A169, T47, A170, A177, A178)
Toxicity LD50: 268 mg/kg (Oral, Rat) (T14) LD50: 790 mg/kg (Oral, Mouse) (T14) LD50: 1300 mg/kg (Oral, Guinea pig) (T14)
Lethal Dose
Carcinogenicity 2B, possibly carcinogenic to humans. (L135)
Uses/Sources It is a high explosive and one of the precursors for trinitrotoluene (TNT), which is synthesized through three separate nitrations of toluene. 2,4-Dinitrotoluene can affect the body if it is inhaled, comes in contact with the eyes or skin, is swallowed, or is absorbed through the skin. Even a small amount absorbed from clothes or shoes may cause toxic symptoms. It is assumed that oral ingestion could be a secondary route for occupationally exposed humans. (L270, T44)
Minimum Risk Level Acute Oral: 0.05 mg/kg/day (L134) Chronic Oral: 0.002 mg/kg/day (L134)
Health Effects 2,4-Dinitrotoluene poisoning may cause methemoglobinemia, anemia, leukopenia, and liver necrosis. Liver injury may be more common than cyanosis. (T48, L276)
Symptoms Symptoms of 2,4-dinitrotoluene poisoning include blue lips or finger nails, blue skin, vertigo, fatigue, dizziness, weakness, nausea, vomiting, dyspnea, arthralgia, insomnia, tremor, paralysis, unconsciousness, chest pain, shortness of breath, palpitation, anorexia, and loss of weight. (T45, L272)
Treatment Following oral exposure, immediately dilute with 4 to 8 ounces (120 to 240 mL) of water or milk (not to exceed 4 ounces/120 mL in a child). Administer charcoal as a slurry. Gastric lavage and oxygen administration is recommended. Following inhalation exposure, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Following eyes exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water, and administer a benzodiazepine IV in case of irritation. In all those cases, a physician may need to examine the area if irritation or pain persists. (T36)
DrugBank ID
HMDB ID
PubChem Compound ID 8461
ChEMBL ID CHEMBL259865
ChemSpider ID 8150
KEGG Compound ID C11006
UniProt ID 0
OMIM ID 0
ChEBI ID 920
BioCyc ID CPD-1125
CTD ID C016403
Stitch ID 2,4-Dinitrotoluene
PDB ID
ACToR ID 539
Wikipedia Link http://en.wikipedia.org/wiki/2,4-Dinitrotoluene
Creation Date 2009-03-06 18:58:04
Update Date 2014-12-24 20:21:06