13-06449. Narcobarbital [Archived]

Nomenclature

CAS number: 125-55-3
5-(2-Bromo-2-propenyl)-1-methyl-5-(1-methylethyl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-(2-bromoallyl)-5-isopropyl-1-methylbarbituric acid; N-methyl-β-bromoallylisopropylbarbituric acid; 5-isopropyl-5-(β-bromoallyl)-N-methylbarbituric acid; enibomal.
C11H15BrN2O3; mol wt 303.15.
C 43.58%, H 4.99%, Br 26.36%, N 9.24%, O 15.83%.

Description and references

Prepd by heating 5-isopropyl-1-methylbarbituric acid with 2,3-dibromo-1-propene in alkaline soln: Boedecker, Gruber, DE 613403 (1937 to Riedel de Haen). See also DE 627380; US 2080071.

Chemical structure

Properties

Crystals from dilute ethanol, mp 115°. Bitter taste. Very sparingly sol in water. Sol in methanol, ethanol, pyridine, alkaline aq solns.

Derivative

Sodium salt.

Nomenclature

CAS number: 3329-16-6
Eunarcon (Parke-Davis).
C11H14BrN2NaO3; mol wt 325.13.
C 40.64%, H 4.34%, Br 24.58%, N 8.62%, Na 7.07%, O 14.76%.

Properties

Alkaline, water-soluble.

Note

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

Therapeutic Category

Sedative, hypnotic; anticonvulsant.

Keywords

Anticonvulsant; Sedative/Hypnotic; Barbituric Acid Derivatives

Status

This monograph has been retired and is no longer subject to revision or update.