756. Aprobarbital

Nomenclature

CAS number: 77-02-1
5-(1-Methylethyl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-allyl-5-isopropylbarbituric acid; allypropymal; Alurate (Roche).
C10H14N2O3; mol wt 210.23.
C 57.13%, H 6.71%, N 13.33%, O 22.83%.

Description and references

Prepn: US 1444802 (1923). Toxicity data: H. H. Frey, Arzneim.-Forsch. 12, 389 (1962).

Chemical structure

Properties

Slightly bitter crystals, mp 140-141.5°. Almost insoluble in water, petr ether, aliphatic hydrocarbons. Sol in alcohol, chloroform, ether, acetone, benzene, glacial acetic acid, also in solns of fixed alkali hydroxides. A satd aq soln is acid to litmus. LD50 i.p. in mice: 200 mg/kg (Frey).

Derivative

Sodium salt.

Nomenclature

CAS number: 125-88-2
Aprobarbital sodium; sodium 5-allyl-5-isopropylbarbiturate.
C10H13N2NaO3; mol wt 232.21.
C 51.72%, H 5.64%, N 12.06%, Na 9.90%, O 20.67%.

Properties

Hygroscopic powder; slightly bitter taste. Very soluble in water; slightly sol in alc. Practically insol in ether. Aq solns are alkaline to litmus.

Note

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

Therapeutic Category

Sedative, hypnotic.

Keywords

Sedative/Hypnotic; Barbituric Acid Derivatives