2,6-Dinitrotoluene (T3D0261)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (12)XML
Targets (12)
Record Information
Version2.0
Creation Date2009-03-06 18:58:23 UTC
Update Date2014-12-24 20:21:25 UTC
Accession NumberT3D0261
Identification
Common Name2,6-Dinitrotoluene
ClassSmall Molecule
Description2,6-Dinitrotoluene is one 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. (5)
Compound Type
  • Aromatic Hydrocarbon
  • Explosive Agent
  • Industrial/Workplace Toxin
  • Nitrite
  • Organic Compound
  • Plasticizer
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,3-Dinitro 2-methyl benzene
1-Methyl-2,6-dinitrobenzene
2,4-/2,6-Dinitrotoluene mixture
2,6-dinitromethylbenzene
2,6-DNT
2-Methyl-1,3-dinitro-benzene
2-methyl-1,3-dinitrobenzene
DNT
Chemical FormulaC7H6N2O4
Average Molecular Mass182.134 g/mol
Monoisotopic Mass182.033 g/mol
CAS Registry Number606-20-2
IUPAC Name2-methyl-1,3-dinitrobenzene
Traditional Name2,6-dinitrotoluene
SMILESCC1=C(C=CC=C1[N+]([O-])=O)[N+]([O-])=O
InChI IdentifierInChI=1S/C7H6N2O4/c1-5-6(8(10)11)3-2-4-7(5)9(12)13/h2-4H,1H3
InChI KeyInChIKey=XTRDKALNCIHHNI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dinitrotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and exactly two nitro groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
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
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point66°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP1.81ALOGPS
logP2.37ChemAxon
logS-3.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area91.64 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.75 m³·mol⁻¹ChemAxon
Polarizability15.45 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0032-9400000000-187f76ebf7bf7a3b53ee2021-09-23View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-cdceb2b78695e9fc35482016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0900000000-7963147e1fc7b2b2f6712016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-057i-1900000000-af99bdbd9be26e87e7082016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-516591494f516055d4c02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-5fc7b4abdf242577d41e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ai-1900000000-83598c0a5f572aec6db02016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-02vl-9400000000-c50d5d0c3a8c5a66e6b12014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureDermal (2) ; eye contact (2) ; inhalation (2) ; oral (2)
Mechanism of ToxicityDinitrotoluene 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 dinitrotoluene 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. (6)
MetabolismThe metabolism of 2,6-DNT occurs in the liver and also in the intestine by microflora. Both oxidized and reduced metabolites are excreted in the urine after oral administration of the compound. Oxidative metabolism by cytochrome P450 predominates in the liver, leading to the formation of dinitrobenzyl alcohol which is either converted to glucuronide conjugate or further oxidized to dinitrobenzoic acid. Dinitrobenzyl alcohol glucuronide is partially excreted into the bile, followed by metabolism by gut microflora and enterohepatic cycling (nitroreductase). Thus, 2,6-DNT appears to be first metabolized by the liver with the metabolites being excreted into the bile; the biliary metabolites are hydrolyzed and further metabolized in the intestine; after reabsorption and circulation back to the liver, a portion of the metabolites (2-amino-6-nitrobenzyl) are oxidized to a hydroxylamine by hepatic enzymes. The hydroxylamine is then conjugated with sulfate by hepatic sulfotransferase. The unstable N-sulfate decomposes to form an electrophilic nitrenium ion, which can react with cellular nucleophiles such as DNA. 2,6-Dinitrobenzyl alcohol glucuronide, 2-amino-6-nitrotoluene, and 2,6-dinitrobenzaldehyde can be detected in the bile. Some amounts of 2,6-dinitrobenzylalcohol and 2-amino-6nitrobenzyl alcohol can also be found. (6)
Toxicity ValuesLD50: 180-795 mg/kg/day (Oral, Rat) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesIt is a high explosive and one of the precursors for trinitrotoluene (TNT), which is synthesized through three separate nitrations of toluene. 2,6-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. (5, 2)
Minimum Risk LevelIntermediate Oral: 0.004 mg/kg/day (Dog) (511)
Health Effects2,6-Dinitrotoluene poisoning may cause methemoglobinemia, anemia, leukopenia, and liver necrosis. Liver injury may be more common than cyanosis. (6)
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. (3, 7)
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. (1)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID11813
ChEMBL IDCHEMBL1328508
ChemSpider ID11320
KEGG IDC11008
UniProt IDNot Available
OMIM ID
ChEBI ID957
BioCyc IDCPD-1125
CTD IDNot Available
Stitch ID2,6-Dinitrotoluene
PDB IDNot Available
ACToR ID538
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0261.pdf
General References
  1. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  2. 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.
  3. USEPA (1980). Ambient Water Quality Criteria Doc: Dinitrotoluene. EPA 440/5-80-045.
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  5. Wikipedia. 2,4-Dinitrotoluene. Last Updated 10 June 2009. [Link]
  6. 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]
  7. International Programme on Chemical Safety (IPCS) INCHEM (2005). Poison Information Monograph for 2,6-Dinitritoluene. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Hemoglobin subunit alpha
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]
2. 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. 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]
Target Details
3. Hemoglobin subunit beta
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]
Target Details
4. Hemoglobin subunit delta
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]
Target Details
5. Hemoglobin subunit epsilon
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]
Target Details
6. Hemoglobin subunit gamma-1
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]
Target Details
7. Hemoglobin subunit gamma-2
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]
Target Details
8. Hemoglobin subunit mu
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]
Target Details
9. Hemoglobin subunit theta-1
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]
Target Details
10. Hemoglobin subunit zeta
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. 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]
Target Details
12. Retinoic acid receptor gamma
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. Required for limb bud development. In concert with RARA or RARB, required for skeletal growth, matrix homeostasis and growth plate function (By similarity).
Gene Name:
RARG
Uniprot ID:
P13631
Molecular Weight:
50341.405 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.93 uMATG_RARg_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]