4704. Hexobarbital

Nomenclature

CAS number: 56-29-1
5-(1-Cyclohexen-1-yl)-1,5-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-(1-cyclohexen-1-yl)-1,5-dimethylbarbituric acid; 5-cyclohexenyl-3,5-dimethylbarbituric acid; methylhexabital; methexenyl; enhexymal; hexobarbitone; Citodon; Citopan; Cyclonal; Dorico; Evipal (Winthrop); Evipan (Bayer); Hexanastab Oral; Noctivane; Sombucaps; Sombulex (3M Pharma); Somnalert (Warren-Teed).
C12H16N2O3; mol wt 236.27.
C 61.00%, H 6.83%, N 11.86%, O 20.31%.

Description and references

Prepd by condensation of monomethylurea with methyl cyclohexenylmethylcyanoacetate in abs alcohol in the presence of sodium: US 1947944; cf. DE 595175; FR 753178. Comparative clinical trial in anesthesia: D. W. Barron et al., Br. J. Anaesth. 38, 802 (1966). GC determn in human plasma: D. D. Breimer, J. M. Van Rossum, J. Chromatogr. 88, 235 (1974). Pharmacokinetics: N. P. E. Vermeulen et al., Br. J. Clin. Pharmacol. 15, 459 (1983); M. Van der Graaff et al., Biopharm. Drug Dispos. 7, 265 (1986).

Chemical structure

Properties

Prismatic crystals, practically tasteless, mp 145-147°. Practically insol in water. One gram dissolves in about 3 liters of water. Sol in methanol, hot ethanol, ether, chloroform, acetone, benzene, aq solns of alkali hydroxides, but not carbonates.

Derivative

Sodium salt.

Nomenclature

CAS number: 50-09-9
Hexobarbital soluble; Cyclonal Sodium; Dorico Soluble; Evipal Sodium (Winthrop); Evipan Sodium (Bayer); Hexanastab; Hexenal; Methexenyl Sodium; Noctivane Sodium; Narcosan Soluble; Privenal.
C12H15N2NaO3; mol wt 258.25.
C 55.81%, H 5.85%, N 10.85%, Na 8.90%, O 18.59%.

Properties

White, bitter, very hygroscopic powder. Very sol in water, freely sol in alcohol, methanol, acetone. Practically insol in chloroform, ether, benzene. A soln in water absorbs carbon dioxide from the air, causing precipitation of the insol free acid. Aq and alcoholic solns are alkaline to litmus and phenolphthalein. The pH of a 10% w/v soln of hexobarbital soluble is about 11.5.

Note

This is a controlled substance (depressant): 21 CFR, 1308.13.

Therapeutic Category

Sedative, hypnotic. Anesthetic (intravenous).

Therapeutic Category (Veterinary)

Sedative, hypnotic.

Keywords

Anesthetic (Intravenous); Sedative/Hypnotic; Barbituric Acid Derivatives