4477. Glutethimide

Nomenclature

CAS number: 77-21-4
3-Ethyl-3-phenyl-2,6-piperidinedione; 2-ethyl-2-phenylglutarimide; α-ethyl-α-phenylglutarimide; 3-ethyl-3-phenyl-2,6-dioxopiperidine; 3-ethyl-3-phenyl-2,6-diketopiperidine; Elrodorm; Doriden (Novartis).
C13H15NO2; mol wt 217.26.
C 71.87%, H 6.96%, N 6.45%, O 14.73%.

Description and references

Synthesis: Tagmann et al., Helv. Chim. Acta 35, 1541 (1952); Salmon-Legagneur, Neveu, Compt. Rend. 234, 1060 (1952); Bull. Soc. Chim. Fr. 1953, 70; Hoffmann, Tagmann, US 2673205 (1954 to Ciba). Resolution: Kukalja et al., Croat. Chem. Acta 33, 41 (1961), C.A. 55, 27193g (1961). Abs config of antipodes: Finch et al., Experientia 31, 1002 (1975). Comprehensive description: H. Y. Aboul-Enein, Anal. Profiles Drug Subs. 5, 139-187 (1976).

Chemical structure

Derivative

dl-Form.

Properties

Crystals from ether or from ethyl acetate + petr ether, mp 84°. uv max (methanol): 251, 257, 263 nm. Freely sol in ethyl acetate, acetone, ether, chloroform; sol in ethanol, methanol. Practically insol in water.

Derivative

d-Form.

Properties

Crystals, mp 102.5-103°. [α]D20 +176° (methanol).

Derivative

l-Form.

Properties

Crystals, mp 102-103°. [α]D20 181° (methanol).

Note

This is a controlled substance (depressant): 21 CFR, 1308.12.

Therapeutic Category

Sedative; hypnotic.

Keywords

Sedative/Hypnotic; Piperidinediones