Nitroglycerin

Nitroglycerin

Names
Preferred IUPAC name Propane-1,2,3-triyl trinitrate
Other names 1,2,3-Tris(nitrooxy)propane
Identifiers
CAS Number	55-63-0 Y
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	1802063
ChEBI	CHEBI:28787 Y
ChEMBL	ChEMBL730 Y
ChemSpider	4354 Y
DrugBank	DB00727 Y
ECHA InfoCard	100.000.219
EC Number	200-240-8
Gmelin Reference	165859
IUPHAR/BPS	7053
KEGG	D00515 Y
MeSH	Nitroglycerin
PubChem	4510
UNII	G59M7S0WS3 Y
UN number	0143, 0144, 1204, 3064, 3319
InChI InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2 Y Key: SNIOPGDIGTZGOP-UHFFFAOYSA-N Y InChI=1/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2 Key: SNIOPGDIGTZGOP-UHFFFAOYAR
SMILES C(C(CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-] o:n(:o)OCC(COn(:o):o)On(:o):o
Properties
Chemical formula	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
Solubility in water	slightly
Solubility	acetone, ether, benzene, alcohol
log P	2.154
Structure
Coordination geometry	Tetragonal at C1, C2, and C3 Trigonal planar at N7, N8, and N9
Molecular shape	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
Std enthalpy of formation (ΔfHo298)	−370 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−1.529 MJ mol−1
Pharmacology
ATC code	C01DA02 (WHO) C05AE01 (WHO)
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Intravenous, Oral, Sublingual, Topical, Transdermal
Pharmacokinetics:
Bioavailability	<1%
Metabolism	Hepatic
Biological half-life	3 min
Legal status	AU: S3 (Pharmacist only)
Hazards
Main hazards	Explosive
EU classification (DSD)	E T+ N
R-phrases	R3, R12, R26/27/28, R33, R51/53
S-phrases	(S1/2), S33, S35, S36/37, S45, S53, S61
NFPA 704	2 2 4
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).
Y  (what is YN ?)
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.