7138. Pentrinitrol

Nomenclature

CAS number: 1607-17-6
2,2-Bis[(nitrooxy)methyl]-1,3-propanediol mononitrate (ester); pentaerythritol trinitrate; W-2197; Petrin (Parke-Davis).
C5H9N3O10; mol wt 271.14.
C 22.15%, H 3.35%, N 15.50%, O 59.01%.

Description and references

Coronary vasodilator related to pentaerythritol tetranitrate, q.v. Prepn (no data given): DE 638422; DE 638423 (both 1936 to Westf"alisch-Anhaltisch Sprengstoff), C.A. 31, 12122(1937); N. J. Marans et al., J. Am. Chem. Soc. 76, 1304 (1954); A. T. Camp et al., ibid. 77, 751 (1955); J. Simecek, Collect. Czech. Chem. Commun. 27, 362 (1962). Use in coronary insufficiency: F. J. DiCarlo, US 3419571 (1968 to Warner-Lambert). Electrical moment and molecular rotation: A. R. Lawrence, A. J. Matuszko, J. Phys. Chem. 65, 1903 (1961). Chromatographic determn: I. W. F. Davidson et al., J. Chromatogr. 57, 345 (1971). Metabolism: F. J. DiCarlo et al., Clin. Pharmacol. Ther. 22, 309 (1977). Comparative duration of action: J. Vohra et al., Aust. N.Z. J. Med. 9, 554 (1979).

Chemical structure

Properties

Viscous liq. nD20 1.4941. d420 1.554. Viscosity (cSt): 166.8 (40°); 77.8 (50°). Soly in water: 0.705 g/100 ml at 20°; in benzene: 21.40 g/100 ml at 20°. Very sol in ethanol, ether. Forms a cryst hydrate, mp 32°, when washed with water and allowed to stand overnight at 20°; returns to unhydrated form when allowed to stand at 60° for 2 hrs. When used medicinally it is usually diluted with lactose or mannitol to reduce explosive liability, see pentaerythritol tetranitrate.

Therapeutic Category

Vasodilator (coronary).

Keywords

Vasodilator (Coronary)