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Glyceryl trinitrate

Nitroglycerin
Skeletal formula of zwitterionic nitroglycerin
Ball and stick model of nitroglycerin
Spacefill model of nitroglycerin
Names
Preferred IUPAC name
Propane-1,2,3-triyl trinitrate
Other names
1,2,3-Tris(nitrooxy)propane
Identifiers
55-63-0 YesY
3D model (Jmol) Interactive image
Interactive image
1802063
ChEBI CHEBI:28787 YesY
ChEMBL ChEMBL730 YesY
ChemSpider 4354 YesY
DrugBank DB00727 YesY
ECHA InfoCard 100.000.219
EC Number 200-240-8
165859
7053
KEGG D00515 YesY
MeSH Nitroglycerin
PubChem 4510
UNII G59M7S0WS3 YesY
UN number 0143, 0144, 1204, 3064, 3319
Properties
C3H5N3O9
Molar mass 227.09 g·mol−1
Appearance Colorless liquid
Density 1.6 g cm−3 (at 15 °C)
Melting point 14 °C (57 °F; 287 K)
Boiling point 50 °C (122 °F; 323 K) explodes
slightly
Solubility acetone, ether, benzene, alcohol
log P 2.154
Structure
Tetragonal at C1, C2, and C3

Trigonal planar at N7, N8, and N9

Tetrahedral at C1, C2, and C3

Dihedral at N7, N8, and N9

Explosive data
Shock sensitivity High
Friction sensitivity High
Detonation velocity 7700 m s−1
RE factor 1.50
Thermochemistry
−370 kJ mol−1
−1.529 MJ mol−1
Pharmacology
C01DA02 (WHO) C05AE01 (WHO)
  • US: C (Risk not ruled out)
Intravenous, Oral, Sublingual, Topical, Transdermal
Pharmacokinetics:
<1%
Hepatic
3 min
Legal status
  • AU: S3 (Pharmacist only)
Hazards
Main hazards Explosive
Explosive E Very Toxic T+ Dangerous for the Environment (Nature) N
R-phrases R3, R12, R26/27/28, R33, R51/53
S-phrases (S1/2), S33, S35, S36/37, S45, S53, S61
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g., nitroglycerin Special hazards (white): no codeNFPA 704 four-colored diamond
US health exposure limits (NIOSH):
PEL (Permissible)
C 0.2 ppm (2 mg/m3) [skin]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Trigonal planar at N7, N8, and N9

Dihedral at N7, N8, and N9

Nitroglycerin (NG), also known as nitroglycerine, trinitroglycerin (TNG), trinitroglycerine, nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a heavy, colorless, oily, explosive liquid most commonly produced by nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is an organic nitrate compound rather than a nitro compound, yet the traditional name is often retained. Invented in 1847, nitroglycerin has been used as an active ingredient in the manufacture of explosives, mostly dynamite, and as such it is employed in the construction, demolition, and mining industries. Since the 1880s, it has been used by the military as an active ingredient, and a gelatinizer for nitrocellulose, in some solid propellants, such as cordite and ballistite.

Nitroglycerin is also a major component in double-based smokeless gunpowders used by reloaders. Combined with nitrocellulose, there are hundreds of powder combinations used by rifle, pistol, and shotgun reloaders.

For over 130 years, nitroglycerin has been used medically as a potent vasodilator (dilation of the vascular system) to treat heart conditions, such as angina pectoris and chronic heart failure. Though it was previously known that these beneficial effects are due to nitroglycerin being converted to nitric oxide, a potent venodilator, it was not until 2002 that the enzyme for this conversion was discovered to be mitochondrial aldehyde dehydrogenase. Nitroglycerin is available in sublingual tablets, sprays, and patches. Other potential suggested uses include adjunct therapy in prostate cancer. It is also used topically, in low doses for the treatment of chronic anal fissures.


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