| Identification | More | [Name]
DL-Glutethimide | [CAS]
77-21-4 | [Synonyms]
2-ethyl-2-phenylglutarimide
3-ETHYL-3-PHENYL-2,6-PIPERIDINEDIONE
D,L-GLUTETHIMIDE
GLUTETHIMIDE
RARECHEM AB PP 2824
(R,S)-3-ethyl-3-phenyl-2,6-piperidinedione
2,6-Piperidinedione, 3-ethyl-3-phenyl-
2,6-piperidinedione,3-ethyl-3-phenyl
2-ethyl-2-phenyl-glutarimid
2-Phenyl-2-ethylglutaric acid imide
2-phenyl-2-ethylglutaricacidimide
3-Ethyl-3-phenyl-2,6-diketopiperidine
3-Ethyl-3-phenyl-2,6-dioxopiperidine
3-Phenyl-3-ethyl-2,6-diketopiperidine
3-Phenyl-3-ethyl-2,6-dioxopiperidine
Alfimid
alpha-Ethyl-alpha-phenylglutarimide
alpha-Phenyl-alpha-ethylglutaric acid imide
alpha-phenyl-alpha-ethylglutaricacidimide
alpha-Phenyl-alpha-ethylglutarimide | [EINECS(EC#)]
201-012-0 | [Molecular Formula]
C13H15NO2 | [MDL Number]
MFCD00056091 | [Molecular Weight]
217.26 | [MOL File]
77-21-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White, crystalline powder.Saturated solution is slightly acid.
Freely soluble in acetone, ethyl acetate, and chloroform; soluble in ethanol and methanol; practically
insoluble in water. | [Melting point ]
84°C | [Boiling point ]
357.82°C (rough estimate) | [density ]
1.0960 (rough estimate) | [refractive index ]
1.5300 (estimate) | [Fp ]
9℃ | [storage temp. ]
-20°C | [pka]
pKa 11.8 (Uncertain) | [Water Solubility ]
0.95g/L(27 ºC) | [CAS DataBase Reference]
77-21-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Glutethimide(77-21-4) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [RIDADR ]
3249 | [WGK Germany ]
1 | [RTECS ]
MA4725000 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29251200 | [Safety Profile]
Poison by ingestion and
intraperitoneal routes. Human systemic effects by
ingestion: pupillary dilation, ataxia, somnolence,
coma, and blood pressure depression. An
experimental teratogen. Other experimental
reproductive effects. When heated to
decomposition it emits toxic fumes of NOx.
Caution: May be habit forming. This is a controlled
substance (depressant) listed in the US. Code of
Federal Regulations, Title 21 Part 1308.13 (1985) | [Hazardous Substances Data]
77-21-4(Hazardous Substances Data) | [Toxicity]
Glutethimide,
and a structurally similar compound methyprylon, has been used
occasionally as a sedative-hypnotic, although glutethimide’s use
for longer than 3 days is not recommended and it is rarely, if
ever, prescribed today. Glutethimide causes a skin rash in nearly
10% of those using it, and although it was once thought to produce
less respiratory depression than the barbiturates its overdose
fatality record is not good. Much of the drug’s action can
be attributed to 4-hydroxyglutethimide, which is more than twice
as potent and has a long half-life. Like many other sedativehypnotics,
abrupt withdrawal after chronic use or abuse
resembles that of ethanol or the barbiturates and must be managed
accordingly. |
| Hazard Information | Back Directory | [Hazard]
Manufacture and use controlled by law. | [Chemical Properties]
White, crystalline powder.Saturated solution is slightly acid.
Freely soluble in acetone, ethyl acetate, and chloroform; soluble in ethanol and methanol; practically
insoluble in water. | [Originator]
Doriden,U.S.V.,US,1955 | [Uses]
Sedative-hypnotic. | [Definition]
ChEBI: Glutethimide is a member of piperidines. | [Manufacturing Process]
The 2-phenyl-2-ethyl-pentane-1,5-diacid-mononitrile-(1) of melting point 72°
to 76°C, used as starting material in this process, can be produced for
example from α-phenyl-butyric acid nitrile by condensation with acrylic acid
methyl ester and subsequent hydrolysis of the thus-obtained 2-phenyl-2-
ethyl-pentane-1,5-diacid-monomethyl ester-mononitrile-(1) of boiling point
176° to 185°C under 12 mm pressure.
140 parts by weight of 2-phenyl-2-ethyl-pentane-1,5-diacid-mononitrile-(1)
are dissolved in 200 parts by volume of glacial acetic acid and, at an initial
temperature of 60°C, 100 parts by volume of concentrated sulfuric acid added
in portions. In this operation the temperature of the reaction mixture rises to
100°C. The whole is finally maintained for a short time on the boiling water
bath, then cooled and poured on ice and neutralized with alkali to a pH of 6.
Extraction with chloroform is then effected and the chloroform extract washed with dilute caustic soda solution, dried over calcium chloride, the chloroform
evaporated and the residue crystallized from ethyl acetate with addition of
ligroin. The obtained 3-phenyl-3-ethyl-2,6-dioxo-piperidine melts at 78° to
81°C. | [Brand name]
C "5";Doridene;Doriden-sed;Doridine;Dorimide;Elrodorm;Gludorm;Sarodormin;Somid;Tardyl. | [Therapeutic Function]
Sedative, Hypnotic | [World Health Organization (WHO)]
Glutethimide, a piperidine derivative, was introduced in 1955 for
use as a sedative-hypnotic drug. Its addiction liability and severity of withdrawal
symptoms are equal to those of the barbiturates and it is controlled under
Schedule III of the 1971 Convention on Psychotropic Substances.
(Reference: (UNCPS3) United Nations Convention on Psychotropic Substances (III),
, , 1971) | [General Description]
Glutethimide, 2-ethyl-2-phenylglutarimide(Doriden), is one of the most active nonbarbituratehypnotics that is structurally similar to the barbiturates,especially phenobarbital. Because of glutethimide’s lowaqueous solubility, its dissolution and absorption from theGI track is somewhat erratic. Consistent with its highlipophilicity, it undergoes extensive oxidative metabolismin the liver with a half-life of approximately 10 hours.Glutethimide is used as a racemic mixture with the (+)enantiomer being primarily metabolized on the glutarimidering and the (—) enantiomer on the phenyl ring. The productof metabolic detoxification is excreted after conjugationwith glucuronic acid at the hydroxyl group. The drug is anenzyme inducer. In the therapeutic dosage range, adverse effectstend to be infrequent. Toxic effects in overdose are assevere as, and possibly more troublesome than, those of thebarbiturates. | [Purification Methods]
Crystallise glutethimide from diethyl ether or ethyl acetate/pet ether. It has m 91-92o (from aqueous EtOH), 87-87.5o (from Et2O/pet ether), 84-87o (from isopropanol), and 83-84o (from Et2O). [Penprase & Biles J Am Pharm Assoc 47 523 1958, Hofmann et al. Helv Chim Acta 40 387, 393 1957, Beilstein 21 III/IV 5493.] The R(+)-enantomer crystallises from EtOAc/pet ether with m 103-104o, and [ ] 20+184o (c 1, |
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