Nitroglycerin

Nitroglycerin (NG), (alternative spelling of nitroglycerine) also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, 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, but the traditional name is retained. Discovered in 1847 by Ascanio Sobrero, nitroglycerin has been used as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. It is combined with nitrocellulose to form double-based smokeless powder, which has been used as a propellant in artillery and firearms since the 1880s.

For the use of this chemical as a drug, see Nitroglycerin (medication).
Nitroglycerin
Names
Preferred IUPAC name
Propane-1,2,3-triyl trinitrate
Other names
  • 1,2,3-Tris(nitrooxy)propane
  • 1,2,3-Trinitroxypropane
  • Glyceryl trinitrate
  • GTN
  • Nitro
  • TNG
  • Trinitroglycerin
  • alpha,alpha,alpha-Trinitroglycerin
Identifiers
3D model (JSmol)
1802063
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.219
EC Number
  • 200-240-8
165859
KEGG
MeSH Nitroglycerin
UNII
UN number 0143, 0144, 1204, 3064, 3319
  • 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
  • C(C(CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
Properties
C3H5N3O9
Molar mass 227.085 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 7,700 m/s
RE factor 1.50
Thermochemistry
−370 kJ⋅mol−1
−1.529 MJ⋅mol−1
Pharmacology
C01DA02 (WHO) C05AE01 (WHO)
Intravenous, by mouth, under the tongue, topical
Pharmacokinetics:
<1%
Liver
3 min
Legal status
  • AU: S3 (Pharmacist only)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Explosive, toxic
GHS labelling:
Danger
H202, H205, H241, H301, H311, H331, H370
P210, P243, P250, P260, P264, P270, P271, P280, P302+P352, P410
NFPA 704 (fire diamond)
3
2
4
NIOSH (US health exposure limits):
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 verify (what is YN ?)
Infobox references

Nitroglycerin has been used for over 130 years in medicine as a potent vasodilator (causing 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, the enzyme for this conversion was only discovered to be mitochondrial aldehyde dehydrogenase (ALDH2) in 2002. Nitroglycerin is available in sublingual tablets, sprays, ointments, and patches.

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