5978. Methitural

Nomenclature

CAS number: 467-43-6
Dihydro-5-(1-methylbutyl)-5-[2-(methylthio)ethyl]-2-thioxo-4,6(1H,5H)-pyrimidinedione; 5-(1-methylbutyl)-5-[2-(methylthio)ethyl]-2-thiobarbituric acid; 5-(2-methylthioethyl)-5-(2-pentyl)-2-thiobarbituric acid.
C12H20N2O2S2; mol wt 288.43.
C 49.97%, H 6.99%, N 9.71%, O 11.09%, S 22.23%.

Description and references

Prepn: Zima, Von Werder, US 2802827 (1957 to E. Merck).

Chemical structure

Derivative

Sodium salt.

Nomenclature

CAS number: 730-68-7
Methioturiate; AM-109; Sch-3132; Neraval (Schering); Thiogenal.
C12H19N2NaO2S2; mol wt 310.41.
C 46.43%, H 6.17%, N 9.02%, Na 7.41%, O 10.31%, S 20.66%.

Properties

Very hygroscopic, yellow crystals. Slight odor of mercaptans. Freely sol in water. pH of a 10% aq soln ≈9.5. Water solns are unstable as evidenced by a deepening of color and formation of a cloudy precipitate upon autoclaving and exposure to light. The addition of sodium carbonate has a stabilizing effect and prevents precipitation for about 24 hrs: Irwin et al., J. Pharmacol. Exp. Ther. 116, 317 (1956).

Note

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

Therapeutic Category

Sedative, hypnotic.

Keywords

Sedative/Hypnotic; Barbituric Acid Derivatives