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Substance Name: Cyclobarbital [INN:BAN:NF]
RN: 52-31-3
UNII: 0M8A98AD9H
InChIKey: WTYGAUXICFETTC-UHFFFAOYSA-N

Note

  • Short to intermediate duration barbiturate used as hypnotic and sedative.

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data

Molecular Formula

  • C12-H16-N2-O3

Molecular Weight

  • 236.2694
 
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Names and Synonyms

Name of Substance

  • Cyclobarbital
  • Cyclobarbital [INN:BAN:NF]

Synonyms

  • 5-(1-Cyclohexen-1-yl)-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
  • 5-(1-Cyclohexen-1-yl)-5-ethylbarbituric acid
  • 5-(1-Cyclohexenyl)-5-ethylbarbituric acid
  • 5-Ethyl-5-cyclohexenylbarbituric acid
  • Adorm
  • Amnosed
  • Cavonyl
  • Ciclobarbital
  • Ciclobarbital [INN-Spanish]
  • Cyclobarbital
  • Cyclobarbitalum
  • Cyclobarbitalum [INN-Latin]
  • Cyclobarbitol
  • Cyclobarbiton
  • Cyclobarbitone
  • Cyclobarbitone [BAN]
  • Cyclobarbitonum
  • Cyclodorm
  • Cyclohexenyl-ethyl barbituric acid
  • Cyklodorm
  • EINECS 200-138-3
  • Ethylhexabital
  • Fanodormo
  • Hexemal
  • Hexemalum
  • Irifan
  • Namuron
  • Palinum
  • Phanodorm
  • Phanodorn
  • Philodorm
  • Pralumin
  • Pro-Sonil
  • Sonaform
  • Tetrahydrophenobarbital
  • UNII-0M8A98AD9H
  • Zyklohexenylaethylbarbitursaeure

Systematic Names

  • 2,4,6-(1H,3H,5H)-Pyrimidinetrione, 5-(1-cyclohexen-1-yl)-5-ethyl-
  • 5-(1-Cyclohexen-1-yl)-5-ethylbarbituric acid
  • Barbituric acid, 5-(1-cyclohexen-1-yl)-5-ethyl-
  • Cyclobarbital

Registry Numbers

CAS Registry Number

  • 52-31-3

FDA UNII

  • 0M8A98AD9H

System Generated Number

  • 0000052313

Structure Descriptors

InChI

1S/C12H16N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h6H,2-5,7H2,1H3,(H2,13,14,15,16,17)

InChIKey

WTYGAUXICFETTC-UHFFFAOYSA-N

Smiles

CCC1(C(=O)NC(=O)NC1=O)C2=CCCCC2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 110mg/kg (110mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of Pharmacology and Experimental Therapeutics. Vol. 33, Pg. 43, 1928.
cat LDLo subcutaneous 100mg/kg (100mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
dog LDLo oral 200mg/kg (200mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
dog LDLo subcutaneous 100mg/kg (100mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
guinea pig LDLo rectal 250mg/kg (250mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 7, Pg. 513, 1960.
human LDLo oral 71mg/kg (71mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 7, Pg. 513, 1960.
mouse LD50 intraperitoneal 255mg/kg (255mg/kg) BEHAVIORAL: SLEEP Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 360, 1959.
mouse LD50 oral 840mg/kg (840mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 242, 1967.
mouse LDLo subcutaneous 300mg/kg (300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT
"Pharmakologische Prufung von Analgetika, Dissertation," Herrlen, G., Pharmakologischen Institut der Universitat Tubingen, Fed. Rep. Ger., 1933Vol. -, Pg. -, 1933.
rabbit LDLo intraperitoneal 130mg/kg (130mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 44, Pg. 325, 1932.
rabbit LDLo intravenous 90mg/kg (90mg/kg)   Journal de Physiologie et de Pathologie Generale. Vol. 30, Pg. 364, 1932.
rabbit LDLo oral 450mg/kg (450mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 44, Pg. 325, 1932.
rabbit LDLo subcutaneous 300mg/kg (300mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD50 intraperitoneal 290mg/kg (290mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 242, 1967.
rat LD50 subcutaneous 210mg/kg (210mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 152, Pg. 341, 1930.
rat LDLo oral 300mg/kg (300mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 182, Pg. 348, 1936.
women TDLo oral 2gm/kg (2000mg/kg) LUNGS, THORAX, OR RESPIRATION: CONSOLIDATION Annals of Internal Medicine. Vol. 37, Pg. 290, 1952.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 173 deg C   EXP
pKa Dissociation Constant 7.51 (none)   EXP
log P (octanol-water) 1.77 (none)   EXP
Water Solubility 1600 mg/L 25 EXP
Vapor Pressure 2.95E-12 mm Hg 25 EST
Henry's Law Constant 5.13E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.78E-11 cm3/molecule-sec 25 EST

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