2,4,6-Trinitrotoluene
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | 2,4,6-Trinitrotoluene(F03334) |
| 2D Structure | |
| 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. (L130) |
| FRCD ID | F03334 |
| CAS Number | 118-96-7 |
| PubChem CID | 8376 |
| Formula | C7H5N3O6 |
| IUPAC Name | 2-methyl-1,3,5-trinitrobenzene |
| InChI Key | SPSSULHKWOKEEL-UHFFFAOYSA-N |
| InChI | InChI=1S/C7H5N3O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3 |
| Canonical SMILES | CC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] |
| Isomeric SMILES | CC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] |
| Wikipedia | 2,4,6-Trinitrotoluene |
| Synonyms |
Tritol
2,4,6-TRINITROTOLUENE
Trinitrotoluene
Trotyl
s-Trinitrotoluol
s-Trinitrotoluene
Tolite
sym-Trinitrotoluol
118-96-7
2-Methyl-1,3,5-trinitrobenzene
|
| Classifies |
Predicted: Illegal Additives
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Nitrobenzenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Nitrobenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 227.132 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 0 |
| Complexity | 292 |
| Monoisotopic Mass | 227.018 |
| Exact Mass | 227.018 |
| XLogP | 1.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Biomonitoring of 2,4,6-trinitrotoluene and degradation products in the marine environment with transplanted blue mussels (M. edulis). | Toxicology | 2017 Sep 1 | 28899748 |
| Differential effects of two explosive compounds on seed germination and seedling morphology of a woody shrub, Morella cerifera. | Ecotoxicology | 2015 Jan | 25336045 |
| The role of nutrients in the biodegradation of 2,4,6-trinitrotoluene in liquid and soil. | J Environ Manage | 2012 May 15 | 22245864 |
| Bioaccumulation of TNT and DDT in sheepshead minnows, Cyprinodon variegatus L.,following feeding of contaminated invertebrates. | Bull Environ Contam Toxicol | 2010 May | 20422149 |
| Toxicological responses of red-backed salamanders (Plethodon cinereus) to subchronic soil exposures of 2,4,6-trinitrotoluene. | Environ Toxicol Chem | 2008 Jun | 18481903 |
| Evaluation of bioremediation methods for the treatment of soil contaminated with explosives in Louisiana Army Ammunition Plant, Minden, Louisiana. | J Hazard Mater | 2007 May 17 | 17289260 |
| Transformation and fate of 2,4,6-trinitrotoluene (TNT) in anaerobic bioslurry reactors under various aeration schemes: implications for the decontamination of soils. | Biodegradation | 2007 Dec | 17273913 |
| Voltammetric determination of nitroaromatic and nitramine explosives contamination in soil. | Talanta | 2006 May 15 | 18970618 |
| Microbiological changes during bioremediation of explosives-contaminated soils inlaboratory and pilot-scale bioslurry reactors. | Bioresour Technol | 2004 Jan | 14592740 |
| Influence of dietary 2,4,6-trinitrotoluene exposure in the northern bobwhite(Colinus virginianus). | Environ Toxicol Chem | 2002 Jan | 11804065 |
| Biotransformation of 2,4,6-trinitrotoluene with Phanerochaete chrysosporium inagitated cultures at pH 4.5. | Appl Environ Microbiol | 1999 Jul | 10388692 |
| Aerobic gram-positive and gram-negative bacteria exhibit differential sensitivityto and transformation of 2,4,6-trinitrotoluene (TNT). | Curr Microbiol | 1997 Aug | 9216880 |
| Six month oral toxicity study of trinitrotoluene in beagle dogs. | Toxicology | 1990 Aug | 2399537 |
| Screening the potential risks of toxic substances using a multimedia compartment model: estimation of human exposure. | Regul Toxicol Pharmacol | 1986 Dec | 3809615 |
| Short-term oral toxicity of a 2,4,6-trinitrotoluene and hexahydro-1,3,5-trinitro-1,3,5-triazine mixture in mice, rats, and dogs. | J Toxicol Environ Health | 1982 Apr | 7108980 |
Targets
- 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
- 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.
References
- 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 ]