| Version |
1.0 |
| Creation Date |
2009-03-06 18:58:02 |
| Update Date |
2010-05-18 20:48:42 |
| Accession Number |
T3D0082 |
| Name |
2,4,6-Trinitrotoluene |
| Compound Type |
- Aromatic Hydrocarbon
- Explosive
- Nitrite
- Organic Compound
- Reagent
|
| 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. (R249) |
| Synonyms |
- 1-Methyl-2,4,6-trinitrobenzene
- 1-methyl-2,4,6-trinitrotoluene
- 2,4, 6-Trinitrotoluene
- 2,4,6-Trinitrotolueen(DUTCH)
- 2,4,6-Trinitrotoluene
- 2,4,6-Trinitrotoluol(GERMAN)
- 2-Methyl-1,3,5-trinitrobenzene
- Alpha-TNT
- Alpha-trinitrotoluol
- Entsufon
- Gradetol
- S-trinitrotoluene
- S-trinitrotoluol
- SYM-trinitrotoluene
- SYM-trinitrotoluol
- SYN-trinitrotoluene
- TNL
- TNT
- TNT-tolite(french)
- Tolit
- Tolite
- Toluene, 2,4,6-trinitro- (wet)
- Trilit
- Trinitrotoluen
- Trinitrotoluene, DRY
- Trinitrotoluene, wet
- Trinitrotoluol
- Tritol
- Tritol (explosive)
- Triton
- Trojnitrotoluen(polish)
- Trotyl
- Trotyl oil
|
| Chemical IUPAC Name |
2-methyl-1,3,5-trinitrobenzene |
| Chemical Formula |
C7H5N3O6 |
| Chemical Structure |
 |
| CAS Registry Number |
118-96-7 |
| 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 |
| PubChem Compound ID |
8376  |
| KEGG ID |
C16391 |
| UniProt ID |
Not Available |
| OMIM ID |
Not Available |
| ChEBI ID |
46053 |
| BioCyc ID |
CPD-9138 |
| SuperToxic ID |
Not Available |
| CTD ID |
D014303 |
| Stitch ID |
2,4,6-Trinitrotoluene |
| DrugBank ID |
Not Available |
| PDB ID |
Not Available |
| ACToR ID |
6562 |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Trinitrotoluene |
| Monoisotopic Mass |
227.017835 |
| MOL File |
Show |
| PDB File |
Show |
| SDF File |
Show |
| SMILES |
CC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O |
| Appearance |
Pale yellow, odorless solid. Loose "needles" before melt-casting. A solid block after being poured into a casing. (R249) |
| Melting Point |
80.1 °C |
| Solubility |
0.115 mg/mL at 23 °C [PHELAN,JM & BARNETT,JL (2001)] |
| Predicted LogP |
2.3066 |
| Route of Exposure |
Oral (R250) ; inhalation (R250) ; dermal (R250) |
| Mechanism of Action |
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. (R296, R297) |
| 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. (R251) |
| Toxicity Values |
Not Available |
| Lethal Dose |
Not Available |
| Carcinogenicity (IARC Classification) |
3, not classifiable as to its carcinogenicity to humans. (R264) |
| 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. (R251) |
| Minimum Risk Level |
Intermediate Oral: 0.0005 mg/kg/day (R260) |
| 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. (R251) |
| 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. (R250) |
| 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. (R251) |
| General References |
- R251 - 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).
- R264 - International Agency for Research on Cancer (2009). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans.
- R260 - 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).
- R297 - 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. [PubMed ]
- R250 - International Occupational Safety and Health Information Centre (2005). International Chemical Safety Card for 2,4,6-Trinitrotoluene.
- R249 - Wikipedia. Trinitrotoluene. Last edited on 20 April 2009.
- R296 - 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. [PubMed ]
|
| Targets |
- Nitric oxide synthase, endothelial
|
|
Target 1
[top]
|
| Target 1 ID |
398 |
| Target 1 Name |
Nitric oxide synthase, endothelial |
| Target 1 Mechanism of Action |
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 endothelial nitric oxide synthase and suppresses l-citrulline formation by shunting electrons away from the normal catalytic pathway. (R296) |
| Target 1 Description |
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 |
| Target 1 Synonyms |
- Endothelial NOS; eNOS; EC-NOS; NOS type III; NOSIII; Constitutive NOS; cNOS
|
| Target 1 Gene Name |
NOS3 |
| Target 1 Protein Sequence |
>Nitric oxide synthase, endothelial
MGNLKSVAQEPGPPCGLGLGLGLGLCGKQGPATPAPEPSRAPASLLPPAPEHSPPSSPLT
QPPEGPKFPRVKNWEVGSITYDTLSAQAQQDGPCTPRRCLGSLVFPRKLQGRPSPGPPAP
EQLLSQARDFINQYYSSIKRSGSQAHEQRLQEVEAEVAATGTYQLRESELVFGAKQAWRN
APRCVGRIQWGKLQVFDARDCRSAQEMFTYICNHIKYATNRGNLRSAITVFPQRCPGRGD
FRIWNSQLVRYAGYRQQDGSVRGDPANVEITELCIQHGWTPGNGRFDVLPLLLQAPDEPP
ELFLLPPELVLEVPLEHPTLEWFAALGLRWYALPAVSNMLLEIGGLEFPAAPFSGWYMST
EIGTRNLCDPHRYNILEDVAVCMDLDTRTTSSLWKDKAAVEINVAVLHSYQLAKVTIVDH
HAATASFMKHLENEQKARGGCPADWAWIVPPISGSLTPVFHQEMVNYFLSPAFRYQPDPW
KGSAAKGTGITRKKTFKEVANAVKISASLMGTVMAKRVKATILYGSETGRAQSYAQQLGR
LFRKAFDPRVLCMDEYDVVSLEHETLVLVVTSTFGNGDPPENGESFAAALMEMSGPYNSS
PRPEQHKSYKIRFNSISCSDPLVSSWRRKRKESSNTDSAGALGTLRFCVFGLGSRAYPHF
CAFARAVDTRLEELGGERLLQLGQGDELCGQEEAFRGWAQAAFQAACETFCVGEDAKAAA
RDIFSPKRSWKRQRYRLSAQAEGLQLLPGLIHVHRRKMFQATIRSVENLQSSKSTRATIL
VRLDTGGQEGLQYQPGDHIGVCPPNRPGLVEALLSRVEDPPAPTEPVAVEQLEKGSPGGP
PPGWVRDPRLPPCTLRQALTFFLDITSPPSPQLLRLLSTLAEEPREQQELEALSQDPRRY
EEWKWFRCPTLLEVLEQFPSVALPAPLLLTQLPLLQPRYYSVSSAPSTHPGEIHLTVAVL
AYRTQDGLGPLHYGVCSTWLSQLKPGDPVPCFIRGAPSFRLPPDPSLPCILVGPGTGIAP
FRGFWQERLHDIESKGLQPTPMTLVFGCRCSQLDHLYRDEVQNAQQRGVFGRVLTAFSRE
PDNPKTYVQDILRTELAAEVHRVLCLERGHMFVCGDVTMATNVLQTVQRILATEGDMELD
EAGDVIGVLRDQQRYHEDIFGLTLRTQEVTSRIRTQSFSLQERQLRGAVPWAFDPPGSDT
NSP
|
| Target 1 Number of Residues |
1203 |
| Target 1 Molecular Weight |
133287.6 |
| Target 1 Theoretical pI |
7.27 |
| Target 1 GO Classification |
|
Function
|
cofactor binding
coenzyme binding
NADP binding
purine nucleotide binding
adenyl nucleotide binding
FAD binding
tetrapyrrole binding
heme binding
protein binding
calmodulin binding
ion binding
cation binding
transition metal ion binding
iron ion binding
monooxygenase activity
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, NAD or NADH as one donor, and incorporation of one atom of oxygen
nitric-oxide synthase activity
binding
nucleotide binding
FMN binding
transporter activity
electron transporter activity
catalytic activity
oxidoreductase activity |
|
Process
|
biosynthesis
nitric oxide biosynthesis
physiological process
metabolism
cellular metabolism
generation of precursor metabolites and energy
electron transport |
|
Component
|
| Not Available |
|
| Target 1 General Function |
Inorganic ion transport and metabolism |
| Target 1 Pathways |
Not Available |
| Target 1 Reactions |
Not Available |
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
|
| Target 1 Essentiality |
Non Essential |
| Target 1 Domain Function |
PF00667:FAD_binding_1
PF00258:Flavodoxin_1
PF00175:NAD_binding_1
PF02898:NO_synthase |
| Target 1 GenBank ID Protein |
Not Available |
| Target 1 UniProtKB ID |
P29474 |
| Target 1 Cellular Location |
Cell membrane. Membrane, caveola. Cytoplasm, cytoskeleton. Golgi apparatus |
| Target 1 Gene Sequence |
>3612 bp
ATGGGCAACTTGAAGAGCGTGGCCCAGGAGCCTGGGCCACCCTGCGGCCTGGGGCTGGGG
CTGGGCCTTGGGCTGTGCGGCAAGCAGGGCCCAGCCACCCCGGCCCCTGAGCCCAGCCGG
GCCCCAGCATCCCTACTCCCACCAGCGCCAGAACACAGCCCCCCGAGCTCCCCGCTAACC
CAGCCCCCAGAGGGGCCCAAGTTCCCTCGTGTGAAGAACTGGGAGGTGGGGAGCATCACC
TATGACACCCTCAGCGCCCAGGCGCAGCAGGATGGGCCCTGCACCCCAAGACGCTGCCTG
GGCTCCCTGGTATTTCCACGGAAACTACAGGGCCGGCCCTCCCCCGGCCCCCCGGCCCCT
GAGCAGCTGCTGAGTCAGGCCCGGGACTTCATCAACCAGTACTACAGCTCCATTAAGAGG
AGCGGCTCCCAGGCCCACGAACAGCGGCTTCAAGAGGTGGAAGCCGAGGTGGCAGCCACA
GGCACCTACCAGCTTAGGGAGAGCGAGCTGGTGTTCGGGGCTAAGCAGGCCTGGCGCAAC
GCTCCCCGCTGCGTGGGCCGGATCCAGTGGGGGAAGCTGCAGGTGTTCGATGCCCGGGAC
TGCAGGTCTGCACAGGAAATGTTCACCTACATCTGCAACCACATCAAGTATGCCACCAAC
CGGGGCAACCTTCGCTCGGCCATCACAGTGTTCCCGCAGCGCTGCCCTGGCCGAGGAGAC
TTCCGAATCTGGAACAGCCAGCTGGTGCGCTACGCGGGCTACCGGCAGCAGGACGGCTCT
GTGCGGGGGGACCCAGCCAACGTGGAGATCACCGAGCTCTGCATTCAGCACGGCTGGACC
CCAGGAAACGGTCGCTTCGACGTGCTGCCCCTGCTGCTGCAGGCCCCAGATGAGCCCCCA
GAACTCTTCCTTCTGCCCCCCGAGCTGGTCCTTGAGGTGCCCCTGGAGCACCCCACGCTG
GAGTGGTTTGCAGCCCTGGGCCTGCGCTGGTACGCCCTCCCGGCAGTGTCCAACATGCTG
CTGGAAATTGGGGGCCTGGAGTTCCCCGCAGCCCCCTTCAGTGGCTGGTACATGAGCACT
GAGATCGGCACGAGGAACCTGTGTGACCCTCACCGCTACAACATCCTGGAGGATGTGGCT
GTCTGCATGGACCTGGATACCCGGACCACCTCGTCCCTGTGGAAAGACAAGGCAGCAGTG
GAAATCAACGTGGCCGTGCTGCACAGTTACCAGCTAGCCAAAGTCACCATCGTGGACCAC
CACGCCGCCACGGCCTCTTTCATGAAGCACCTGGAGAATGAGCAGAAGGCCAGGGGGGGC
TGCCCTGCAGACTGGGCCTGGATCGTGCCCCCCATCTCGGGCAGCCTCACTCCTGTTTTC
CATCAGGAGATGGTCAACTATTTCCTGTCCCCGGCCTTCCGCTACCAGCCAGACCCCTGG
AAGGGGAGTGCCGCCAAGGGCACCGGCATCACCAGGAAGAAGACCTTTAAAGAAGTGGCC
AACGCCGTGAAGATCTCCGCCTCGCTCATGGGCACGGTGATGGCGAAGCGAGTGAAGGCG
ACAATCCTGTATGGCTCCGAGACCGGCCGGGCCCAGAGCTACGCACAGCAGCTGGGGAGA
CTCTTCCGGAAGGCTTTTGATCCCCGGGTCCTGTGTATGGATGAGTATGACGTGGTGTCC
CTCGAACACGAGACGCTGGTGCTGGTGGTAACCAGCACATTTGGGAATGGGGATCCCCCG
GAGAATGGAGAGAGCTTTGCAGCTGCCCTGATGGAGATGTCCGGCCCCTACAACAGCTCC
CCTCGGCCGGAACAGCACAAGAGTTATAAGATCCGCTTCAACAGCATCTCCTGCTCAGAC
CCACTGGTGTCCTCTTGGCGGCGGAAGAGGAAGGAGTCCAGTAACACAGACAGTGCAGGG
GCCCTGGGCACCCTCAGGTTCTGTGTGTTCGGGCTCGGCTCCCGGGCATACCCCCACTTC
TGCGCCTTTGCTCGTGCCGTGGACACACGGCTGGAGGAACTGGGCGGGGAGCGGCTGCTG
CAGCTGGGCCAGGGCGACGAGCTGTGCGGCCAGGAGGAGGCCTTCCGAGGCTGGGCCCAG
GCTGCCTTCCAGGCCGCCTGTGAGACCTTCTGTGTGGGAGAGGATGCCAAGGCCGCCGCC
CGAGACATCTTCAGCCCCAAACGGAGCTGGAAGCGCCAGAGGTACCGGCTGAGCGCCCAG
GCCGAGGGCCTGCAGTTGCTGCCAGGTCTGATCCACGTGCACAGGCGGAAGATGTTCCAG
GCTACAATCCGCTCAGTGGAAAACCTGCAAAGCAGCAAGTCCACGAGGGCCACCATCCTG
GTGCGCCTGGACACCGGAGGCCAGGAGGGGCTGCAGTACCAGCCGGGGGACCACATAGGT
GTCTGCCCGCCCAACCGGCCCGGCCTTGTGGAGGCGCTGCTGAGCCGCGTGGAGGACCCG
CCGGCGCCCACTGAGCCCGTGGCAGTAGAGCAGCTGGAGAAGGGCAGCCCTGGTGGCCCT
CCCCCCGGCTGGGTGCGGGACCCCCGGCTGCCCCCGTGCACGCTGCGCCAGGCTCTCACC
TTCTTCCTGGACATCACCTCCCCACCCAGCCCTCAGCTCTTGCGGCTGCTCAGCACCTTG
GCAGAAGAGCCCAGGGAACAGCAGGAGCTGGAGGCCCTCAGCCAGGATCCCCGACGCTAC
GAGGAGTGGAAGTGGTTCCGCTGCCCCACGCTGCTGGAGGTGCTGGAGCAGTTCCCGTCG
GTGGCGCTGCCTGCCCCACTGCTCCTCACCCAGCTGCCTCTGCTCCAGCCCCGGTACTAC
TCAGTCAGCTCGGCACCCAGCACCCACCCAGGAGAGATCCACCTCACTGTAGCTGTGCTG
GCATACAGGACTCAGGATGGGCTGGGCCCCCTGCACTATGGAGTCTGCTCCACGTGGCTA
AGCCAGCTCAAGCCCGGAGACCCTGTGCCCTGCTTCATCCGGGGGGCTCCCTCCTTCCGG
CTGCCACCCGATCCCAGCTTGCCCTGCATCCTGGTGGGTCCAGGCACTGGCATTGCCCCC
TTCCGGGGATTCTGGCAGGAGCGGCTGCATGACATTGAGAGCAAAGGGCTGCAGCCCACT
CCCATGACTTTGGTGTTCGGCTGCCGATGCTCCCAACTTGACCATCTCTACCGCGACGAG
GTGCAGAACGCCCAGCAGCGCGGGGTGTTTGGCCGAGTCCTCACCGCCTTCTCCCGGGAA
CCTGACAACCCCAAGACCTACGTGCAGGACATCCTGAGGACGGAGCTGGCTGCGGAGGTG
CACCGCGTGCTGTGCCTCGAGCGGGGCCACATGTTTGTCTGCGGCGATGTTACCATGGCA
ACCAACGTCCTGCAGACCGTGCAGCGCATCCTGGCGACGGAGGGCGACATGGAGCTGGAC
GAGGCCGGCGACGTCATCGGCGTGCTGCGGGATCAGCAACGCTACCACGAAGACATTTTC
GGGCTCACGCTGCGCACCCAGGAGGTGACAAGCCGCATACGCACCCAGAGCTTTTCCTTG
CAGGAGCGTCAGTTGCGGGGCGCAGTGCCCTGGGCGTTCGACCCTCCCGGCTCAGACACC
AACAGCCCCTGA
|
| Target 1 GenBank Gene ID |
Not Available |
| Target 1 GeneCard ID |
NOS3 |
| Target 1 GenAtlas ID |
NOS3 |
| Target 1 HGNC ID |
HGNC:7876 |
| Target 1 Chromosome Location |
Not Available |
| Target 1 Locus |
7q36 |
| Target 1 SNPs |
SNPJam Report |
| Target 1 Toxin References |
- R296 - 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. [PubMed ]
|
| Target 1 General References |
1378832; 1379542; 7688726; 7509596; 7519987; 15489334; 7514568 |
