Glutethimide
Title: Glutethimide
CAS Registry Number: 77-21-4
CAS Name: 3-Ethyl-3-phenyl-2,6-piperidinedione
Additional Names: 2-ethyl-2-phenylglutarimide; a-ethyl-a-phenylglutarimide; 3-ethyl-3-phenyl-2,6-dioxopiperidine; 3-ethyl-3-phenyl-2,6-diketopiperidine
Trademarks: Elrodorm; Doriden (Novartis)
Molecular Formula: C13H15NO2
Molecular Weight: 217.26
Percent Composition: C 71.87%, H 6.96%, N 6.45%, O 14.73%
Literature 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).
 
Derivative Type: 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.
Melting point: mp 84°
Absorption maximum: uv max (methanol): 251, 257, 263 nm
 
Derivative Type: d-Form
Properties: Crystals, mp 102.5-103°. [a]D20 +176° (methanol).
Melting point: mp 102.5-103°
Optical Rotation: [a]D20 +176° (methanol)
 
Derivative Type: l-Form
Properties: Crystals, mp 102-103°. [a]D20 -181° (methanol).
Melting point: mp 102-103°
Optical Rotation: [a]D20 -181° (methanol)
 
NOTE: This is a controlled substance (depressant): 21 CFR, 1308.12.
Therap-Cat: Sedative; hypnotic.
Keywords: Sedative/Hypnotic; Piperidinediones.

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