7904. Proxibarbal

Nomenclature

CAS number: 2537-29-3
5-(2-Hydroxypropyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-allyl-5-(2-hydroxypropyl)barbituric acid; 5-allyl-5-(β-hydroxypropyl)barbituric acid; 5-allyl-5-(β-hydroxypropyl)malonylurea; proxibarbital; HH-184; Axeen (Hommel); Centralgol (Zyma); Centralgyl; Ipronal (Biosedra).
C10H14N2O4; mol wt 226.23.
C 53.09%, H 6.24%, N 12.38%, O 28.29%.

Description and references

Prepn: Bobranski et al., Rocz. Chem. 30, 175 (1956), C.A. 51, 438f (1957); GB 953387 (1964 to Hommel A.G.), C.A. 61, 3123a (1964); Smissman et al., J. Med. Chem. 14, 853 (1971). Metabolism: Bobranski et al., Arch. Immunol. Ther. Exp. 10, 895 (1962); B. Lambrey et al., Eur. J. Med. Chem. - Chim. Ther. 15, 463 (1980). Pharmacokinetics: eidem, ibid. 12, 565 (1977).

Chemical structure

Properties

Crystals from benzene + ethanol, mp 157-158°; also reported as mp 166.5-168.5° from acetone + chloroform (Smissman). Moderately sol in water.

Note

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

Therapeutic Category

Sedative, hypnotic.

Keywords

Sedative/Hypnotic; Barbituric Acid Derivatives