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Substance Name: Glutethimide [USP:INN:BAN]
RN: 77-21-4
UNII: C8I4BVN78E
InChIKey: JMBQKKAJIKAWKF-UHFFFAOYSA-N

Note

  • A hypnotic and sedative. Its use has been largely superseded by other drugs.

Molecular Formula

  • C13-H15-N-O2

Molecular Weight

  • 217.266
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Hypnotics and Sedatives
  • Mutation Data
  • Reproductive Effect
  • Sedative-Hypnotic

Superlist Classification Code

  • DEA Schedule II
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Names and Synonyms

Name of Substance

  • Glutethimide
  • Glutethimide [USP:INN:BAN]

MeSH Heading

  • Glutethimide

Synonyms

  • 2,6-Piperidinedione, 3-ethyl-3-phenyl-
  • 2-Ethyl-2-phenylglutarimide
  • 2-Phenyl-2-ethylglutaric acid imide
  • 3-Ethyl-3-phenyl-2,6-diketopiperidine
  • 3-Ethyl-3-phenyl-2,6-dioxopiperidine
  • 3-Ethyl-3-phenyl-2,6-piperidinedione
  • 3-Phenyl-3-ethyl-2,6-diketopiperidine
  • 3-Phenyl-3-ethyl-2,6-dioxopiperidine
  • AI3-50601
  • Alfimid
  • alpha-Ethyl-alpha-phenylglutarimide
  • alpha-Phenyl-alpha-ethylglutaric acid imide
  • alpha-Phenyl-alpha-ethylglutarimide
  • CC 11511
  • Doriden
  • Doriden-sed
  • EINECS 201-012-0
  • Elrodorm
  • Gimid
  • Glimid
  • Glutarimide, 2-ethyl-2-phenyl-
  • Glutathimid
  • Glutethimid
  • Glutethimide
  • Glutethimidum
  • Glutethimidum [INN-Latin]
  • Glutetimid
  • Glutetimida
  • Glutetimida [INN-Spanish]
  • Glutetimide
  • Glutetimide [DCIT]
  • Glutetimidu
  • Glutetimidu [Polish]
  • Gluthetimide
  • HSDB 3088
  • Noxiron
  • Noxyron
  • NSC 95239
  • Ondasil
  • Phenyl-aethyl-glutarsaeureimid
  • Phenyl-aethyl-glutarsaeureimid [German]
  • Rigenox
  • Sarodormin
  • UNII-C8I4BVN78E

Systematic Names

  • 2,6-Piperidinedione, 3-ethyl-3-phenyl-
  • Glutarimide, 2-ethyl-2-phenyl-
  • Glutethimide

Superlist Names

  • DEA No. 2550
  • Dorimide
  • Glutethimide

Registry Numbers

CAS Registry Number

  • 77-21-4

FDA UNII

  • C8I4BVN78E

System Generated Number

  • 0000077214

Structure Descriptors

InChI

1S/C13H15NO2/c1-2-13(10-6-4-3-5-7-10)9-8-11(15)14-12(13)16/h3-7H,2,8-9H2,1H3,(H,14,15,16)

InChIKey

JMBQKKAJIKAWKF-UHFFFAOYSA-N

Smiles

c1([C@@]2(C(NC(=O)CC2)=O)CC)ccccc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 25mg/kg (25mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
American Journal of Diseases of Children. Vol. 130, Pg. 507, 1976.
dog LD50 oral 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Schweizerische Medizinische Wochenschrift. Vol. 85, Pg. 305, 1955.
guinea pig LDLo rectal 400mg/kg (400mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 7, Pg. 513, 1960.
human TDLo oral 12500ug/kg (12.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: SLEEP

SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE
Journal of Forensic Sciences. Vol. 5, Pg. 217, 1960.
human TDLo oral 171mg/kg (171mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
JAMA, Journal of the American Medical Association. Vol. 214, Pg. 1704, 1970.
man LDLo oral 165mg/kg (165mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: CHANGES IN LUNG WEIGHT

BEHAVIORAL: GENERAL ANESTHETIC
New England Journal of Medicine. Vol. 257, Pg. 97, 1957.
man LDLo oral 171mg/kg (171mg/kg)   Journal of Forensic Sciences. Vol. 4, Pg. 111, 1959.
man LDLo unreported 147mg/kg (147mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
monkey LDLo oral 300mg/kg (300mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: GENERAL ANESTHETIC
Toxicology and Applied Pharmacology. Vol. 29, Pg. 75, 1974.
mouse LD50 intraperitoneal 208mg/kg (208mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 32, Pg. 243, 1975.
mouse LD50 intraperitoneal 208mg/kg (208mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 32, Pg. 243, 1975.
mouse LD50 oral 360mg/kg (360mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 233, 1972.
rabbit LD50 oral 600mg/kg (600mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 233, 1972.
rat LD50 oral 600mg/kg (600mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 233, 1972.
women LDLo oral 200mg/kg (200mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: COMA
New England Journal of Medicine. Vol. 257, Pg. 97, 1957.
women TDLo oral 300mg/kg (300mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Journal of Forensic Sciences. Vol. 4, Pg. 111, 1959.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 84 deg C   EXP
pKa Dissociation Constant 9.2 (none)   EXP
log P (octanol-water) 1.9 (none)   EXP
Water Solubility 999 mg/L 30 EXP
Vapor Pressure 1.49E-09 mm Hg 25 EST
Henry's Law Constant 4.78E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.87E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.