2,4,6-Trinitrotoluene (T3D0082)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-03-06 18:58:02 UTC
Update Date2014-12-24 20:21:04 UTC
Accession NumberT3D0082
Identification
Common Name2,4,6-Trinitrotoluene
ClassSmall Molecule
DescriptionTrinitrotoluene (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)
Compound Type
  • Aromatic Hydrocarbon
  • Explosive Agent
  • Food Toxin
  • Indicator and Reagent
  • Industrial/Workplace Toxin
  • Nitrite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1-Methyl-2,4,6-trinitrobenzene
2,4,6-TNT
2,4,6-Trinitrotoluol
s-Trinitrotoluol
sym-Trinitrotoluol
TNT
Trinitrotoluene
Trinitrotoluol
Tritol
Trotyl
Chemical FormulaC7H5N3O6
Average Molecular Mass227.131 g/mol
Monoisotopic Mass227.018 g/mol
CAS Registry Number118-96-7
IUPAC Name2-methyl-1,3,5-trinitrobenzene
Traditional Nameα-tnt
SMILESCC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
InChI IdentifierInChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3
InChI KeyInChIKey=SPSSULHKWOKEEL-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitrotoluene
  • Nitroaromatic compound
  • Toluene
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic 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 RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearancePale yellow, odorless solid. Loose "needles" before melt-casting. A solid block after being poured into a casing. (3)
Experimental Properties
PropertyValue
Melting Point80.1°C
Boiling Point240 °C (L131)
Solubility0.115 mg/mL at 23 °C [PHELAN,JM & BARNETT,JL (2001)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP1.5ALOGPS
logP2.31ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)16.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area137.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.07 m³·mol⁻¹ChemAxon
Polarizability17.9 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, Positivesplash10-004i-6190000000-735664b29a5e158ecc6e2021-09-23View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , negativesplash10-03di-0890000000-f022cff7bafbe39462552017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-f6e342b117ed300d424a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0090000000-92d082746b1341998dfb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v4j-0690000000-bb9a7e5ed2c59b9682322016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-826ba2a9c274efe751602016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-0e8740a26a1b43c5472f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-1190000000-714043def040a5a6a26e2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-9460000000-f13fe3ac3044698c32a42014-09-20View Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of Toxicity2,4,6-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)
Metabolism2,4,6-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)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (7)
Uses/Sources2,4,6-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)
Minimum Risk LevelIntermediate Oral: 0.0005 mg/kg/day (6)
Health EffectsExposition 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)
SymptomsExposure 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)
TreatmentIn 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)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01676
HMDB IDNot Available
PubChem Compound ID8376
ChEMBL IDCHEMBL1236345
ChemSpider ID8073
KEGG IDC16391
UniProt IDNot Available
OMIM ID
ChEBI ID46053
BioCyc IDCPD-9138
CTD IDD014303
Stitch ID2,4,6-Trinitrotoluene
PDB IDNot Available
ACToR ID6562
Wikipedia LinkTrinitrotoluene
References
Synthesis Reference

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.

MSDST3D0082.pdf
General References
  1. Sun Y, Iemitsu M, Shimojo N, Miyauchi T, Amamiya M, Sumi D, Hayashi T, Sun G, Shimojo N, Kumagai Y: 2,4,6-Trinitrotoluene inhibits endothelial nitric oxide synthase activity and elevates blood pressure in rats. Arch Toxicol. 2005 Dec;79(12):705-10. Epub 2005 Jul 16. [16025313 ]
  2. Kumagai Y, Kikushima M, Nakai Y, Shimojo N, Kunimoto M: Neuronal nitric oxide synthase (NNOS) catalyzes one-electron reduction of 2,4,6-trinitrotoluene, resulting in decreased nitric oxide production and increased nNOS gene expression: implication for oxidative stress. Free Radic Biol Med. 2004 Aug 1;37(3):350-7. [15223068 ]
  3. Wikipedia. Trinitrotoluene. Last edited on 20 April 2009. [Link]
  4. International Occupational Safety and Health Information Centre (2005). International Chemical Safety Card for 2,4,6-Trinitrotoluene. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (1996). Toxicological profile for 2,4,6-trinitrotoluene (TNT). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  6. 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]
  7. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Nitric oxide synthase, endothelial
General Function:
Tetrahydrobiopterin binding
Specific Function:
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
Gene Name:
NOS3
Uniprot ID:
P29474
Molecular Weight:
133287.62 Da
References
  1. Sun Y, Iemitsu M, Shimojo N, Miyauchi T, Amamiya M, Sumi D, Hayashi T, Sun G, Shimojo N, Kumagai Y: 2,4,6-Trinitrotoluene inhibits endothelial nitric oxide synthase activity and elevates blood pressure in rats. Arch Toxicol. 2005 Dec;79(12):705-10. Epub 2005 Jul 16. [16025313 ]