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Record Information
Version2.0
Creation Date2009-03-06 18:58:04 UTC
Update Date2014-12-24 20:21:06 UTC
Accession NumberT3D0094
Identification
Common Name2,4-Dinitrotoluene
ClassSmall Molecule
Description2,4-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. (15)
Compound Type
  • Aromatic Hydrocarbon
  • Explosive Agent
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Nitrite
  • Organic Compound
  • Plasticizer
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
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
Chemical FormulaC7H6N2O4
Average Molecular Mass182.134 g/mol
Monoisotopic Mass182.033 g/mol
CAS Registry Number121-14-2
IUPAC Name1-methyl-2,4-dinitrobenzene
Traditional Name2,4-dinitrotoluene
SMILESCC1=C(C=C(C=C1)N(=O)=O)N(=O)=O
InChI IdentifierInChI=1S/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3
InChI KeyInChIKey=RMBFBMJGBANMMK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dinitrotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and exactly two nitro groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentDinitrotoluenes
Alternative Parents
Substituents
  • Dinitrotoluene
  • Nitrobenzene
  • Nitroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell junction
  • Cytosol
  • Endoplasmic reticulum
  • Extracellular
  • Membrane
  • Membrane Fraction
  • Microsome
  • Mitochondrion
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Oxidative phosphorylationNot Availablemap00190
Naphthalene DegradationNot AvailableNot Available
Degradation Of Aromatic CompoundsNot AvailableNot Available
Caffeine MetabolismSMP00028 map00232
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceAt room temperature it is a pale yellow to orange crystalline solid. (19)
Experimental Properties
PropertyValue
Melting Point71°C
Boiling Point250-300°C (decomposes)
Solubility0.2 mg/mL at 25 °C [PHELAN,JM & BARNETT,JL (2001)]; 0.27 mg/mL at 22 °C [SEIDELL,A (1941)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0987 mg/mLALOGPS
logP1.9ALOGPS
logP2.37ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area91.64 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.75 m3·mol-1ChemAxon
Polarizability15.62 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-ff5582d43de35b65047bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0900000000-814205d8ac41814fcb9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-0900000000-66644cf7bead7f4e163aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-a945c933127e627e04f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-0ff4810f78737ce86f22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-1900000000-dbb610db7909036e4b3bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-014r-9500000000-fd5b3e80ec9cfe014f6dView in MoNA
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureDermal (9) ; eye contact (9) ; inhalation (9) ; oral (9)
Mechanism of Toxicity2,4-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. (17, 10, 3, 18)
Metabolism2,4-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. (17, 1, 11, 2, 4, 5)
Toxicity ValuesLD50: 268 mg/kg (Oral, Rat) (6) LD50: 790 mg/kg (Oral, Mouse) (6) LD50: 1300 mg/kg (Oral, Guinea pig) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (14)
Uses/SourcesIt 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. (15, 9)
Minimum Risk LevelAcute Oral: 0.05 mg/kg/day (13) Chronic Oral: 0.002 mg/kg/day (13)
Health Effects2,4-Dinitrotoluene poisoning may cause methemoglobinemia, anemia, leukopenia, and liver necrosis. Liver injury may be more common than cyanosis. (12, 17)
SymptomsSymptoms 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. (10, 16)
TreatmentFollowing 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. (8)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID8461
ChEMBL IDCHEMBL259865
ChemSpider ID8150
KEGG IDC11006
UniProt IDNot Available
OMIM ID
ChEBI ID920
BioCyc IDCPD-1125
CTD IDC016403
Stitch ID2,4-Dinitrotoluene
PDB IDNot Available
ACToR ID539
Wikipedia Link2,4-Dinitrotoluene
References
Synthesis ReferenceNot Available
MSDST3D0094.pdf
General References
  1. Guest D, Schnell SR, Rickert DE, Dent JG: Metabolism of 2,4-dinitrotoluene by intestinal microorganisms from rat, mouse, and man. Toxicol Appl Pharmacol. 1982 Jun 15;64(1):160-8. [7112581 ]
  2. Turner MJ Jr, Levine RJ, Nystrom DD, Crume YS, Rickert DE: Identification and quantification of urinary metabolites of dinitrotoluenes in occupationally exposed humans. Toxicol Appl Pharmacol. 1985 Aug;80(1):166-74. [4024104 ]
  3. Dixit R, Schut HA, Klaunig JE, Stoner GD: Metabolism and DNA binding of 2,6-dinitrotoluene in Fischer-344 rats and A/J mice. Toxicol Appl Pharmacol. 1986 Jan;82(1):53-61. [3945944 ]
  4. Mori M, Matsuhashi T, Miyahara T, Shibata S, Izima C, Kozuka H: Reduction of 2,4-dinitrotoluene by Wistar rat liver microsomal and cytosol fractions. Toxicol Appl Pharmacol. 1984 Oct;76(1):105-12. [6548324 ]
  5. Gong P, Kuperman RG, Sunahara GI: Genotoxicity of 2,4- and 2,6-dinitrotoluene as measured by the Tradescantia micronucleus (Trad-MCN) bioassay. Mutat Res. 2003 Jul 8;538(1-2):13-8. [12834750 ]
  6. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  7. Verschueren K (1983). Handbook of Environmental Data of Organic Chemicals. 2nd ed. New York, NY: Van Nostrand Reinhold Co.
  8. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  9. Mackison FW, Stricoff RS, and Partridge LJ Jr. (eds) (1981). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office.
  10. USEPA (1980). Ambient Water Quality Criteria Doc: Dinitrotoluene. EPA 440/5-80-045.
  11. Turner MJ; CIIT 6 (2): 1-3 (1986)
  12. Gosselin RE, Smith RP, and Hodge HC (1984). Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins.
  13. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  14. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  15. Wikipedia. 2,4-Dinitrotoluene. Last Updated 10 June 2009. [Link]
  16. International Programme on Chemical Safety (IPCS) INCHEM (2005). Poison Information Monograph for 2,4-Dinitrotoluene. [Link]
  17. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  18. US Environmental Protection Agency (2008). Drinking Water Health Advisory for 2,4-Dinitrotoluene and 2,6-Dinitrotoluene. [Link]
  19. Wikipedia. Dinitrotoluene. Last Updated 10 June 2009. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Dixit R, Schut HA, Klaunig JE, Stoner GD: Metabolism and DNA binding of 2,6-dinitrotoluene in Fischer-344 rats and A/J mice. Toxicol Appl Pharmacol. 1986 Jan;82(1):53-61. [3945944 ]
  2. USEPA (1980). Ambient Water Quality Criteria Doc: Dinitrotoluene. EPA 440/5-80-045.
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBA1
Uniprot ID:
P69905
Molecular Weight:
15257.405 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:
HBB
Uniprot ID:
P68871
Molecular Weight:
15998.34 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:
HBD
Uniprot ID:
P02042
Molecular Weight:
16055.41 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
Gene Name:
HBE1
Uniprot ID:
P02100
Molecular Weight:
16202.71 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Gene Name:
HBG1
Uniprot ID:
P69891
Molecular Weight:
16140.37 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Specific Function:
Heme binding
Gene Name:
HBG2
Uniprot ID:
P69892
Molecular Weight:
16126.35 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBM
Uniprot ID:
Q6B0K9
Molecular Weight:
15617.97 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
Not Available
Gene Name:
HBQ1
Uniprot ID:
P09105
Molecular Weight:
15507.575 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Oxygen transporter activity
Specific Function:
The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
Gene Name:
HBZ
Uniprot ID:
P02008
Molecular Weight:
15636.845 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for 2,4-,and 2,6-dinitrotoluene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
11. RNA
References
  1. Rickert DE, Schnell SR, Long RM: Hepatic macromolecular covalent binding and intestinal disposition of [14C]dinitrotoluenes. J Toxicol Environ Health. 1983 Apr-Jun;11(4-6):555-67. [6620401 ]