Erythritol tetranitrate

Erythritol tetranitrate
Skeletal formula of erythritol tetranitrate
Ball-and-stick model of the erythritol tetranitrate molecule
Names
IUPAC name
[(2R,3R)-1,3,4-Trinitrooxybutan-2-yl] nitrate
Other names
Erythrityl tetranitrate (INN)
Identifiers
3D model (JSmol)
1730082
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.027.940 Edit this at Wikidata
EC Number
  • 230-734-9
KEGG
UNII
  • InChI=1S/C4H6N4O12/c9-5(10)17-1-3(19-7(13)14)4(20-8(15)16)2-18-6(11)12/h3-4H,1-2H2/t3-,4+ checkY
    Key: SNFOERUNNSHUGP-ZXZARUISSA-N checkY
  • InChI=1/C4H6N4O12/c9-5(10)17-1-3(19-7(13)14)4(20-8(15)16)2-18-6(11)12/h3-4H,1-2H2/t3-,4+
    Key: SNFOERUNNSHUGP-ZXZARUISBH
  • C(C(C(CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
Properties
C4H6N4O12
Molar mass 302.108 g·mol−1
Density 1.7219 (±0.0025) g/cm3
Melting point 61 °C (142 °F; 334 K)
Boiling point Decomposes at 160 °C
0.00302 g/100 mL
Hazards
GHS labelling:
GHS01: Explosive GHS03: Oxidizing GHS07: Exclamation mark
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazard OX: Oxidizer. E.g. potassium perchlorate
1
1
3
OX
Explosive data
Shock sensitivity Medium (2.0 Nm)
Friction sensitivity Medium
Detonation velocity 8200 m/s
RE factor 1.60
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN,[1] though it is thought to be slightly more sensitive to friction and impact.

Like many nitrate esters, ETN acts as a vasodilator, and was the active ingredient in the original "sustained release" tablets, made under a process patent in the early 1950s, called "nitroglyn".[citation needed] Ingesting ETN or prolonged skin contact can lead to absorption and what is known as a "nitro headache".

  1. ^ Erythritol tetranitrate was first synthesized by British chemist John Stenhouse (1809–1880) in 1849. He extracted the simple sugar erythritol (which he called "erythroglucin") from lichen and then studied its chemistry. See: John Stenhouse (1 January 1849) "Examination of the proximate principles of some of the lichens. Part II," Philosophical Transactions of the Royal Society (London), vol. 139, pages 393-401. Reprinted in German as: John von Stenhouse (1849) "Über die näheren Bestandtheile einige Flechten," Justus Liebigs Annalen der Chemie und Pharmacie, vol. 70, no. 2, pages 218-228. Condensed version (in German): John Stenhouse (12 Sept. 1849) "Über die näheren Bestandtheile einige Flechten," Pharmaceutisches Centralblatt, vol. 20, no. 40, pages 625–628.