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Substance Name: Hexobarbital [USP:INN:BAN:JAN]
RN: 56-29-1
UNII: AL8Z8K3P6S
InChIKey: UYXAWHWODHRRMR-UHFFFAOYSA-N

Note

  • A barbiturate that is effective as a hypnotic and sedative.

Molecular Formula

  • C12-H16-N2-O3

Molecular Weight

  • 236.2694
 

Classification Codes

  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • GABA Agents
  • GABA Modulators
  • Hypnotics and Sedatives
  • Mutation Data
  • Neurotransmitter Agents
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Names and Synonyms

Name of Substance

  • Hexobarbital
  • Hexobarbital [USP:INN:BAN:JAN]

MeSH Heading

  • Hexobarbital

Synonyms

  • 1,5-Dimethyl-5-(1-cyclohexenyl)barbituric acid
  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-
  • 5-(1-Cyclohexen-1-yl)-1,5-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
  • 5-(1-Cyclohexen-1-yl)-1,5-dimethylbarbituric acid
  • 5-(1-Cyclohexenyl-1)-1-methyl-5-methylbarbituric acid
  • 5-(delta-1,2-Cyclohexenyl)-5-methyl-N-methyl-barbitursaeure
  • 5-(delta-1,2-Cyclohexenyl)-5-methyl-N-methyl-barbitursaeure [German]
  • AI3-61892
  • Barbidorm
  • Citodon
  • Citopan
  • Cyclonal
  • Cyclopan
  • Dorico
  • EINECS 200-264-9
  • Enhexymal
  • Enhexymalum
  • Esobarbitale
  • Esobarbitale [DCIT]
  • Esobarbitale [Italian]
  • Evipal
  • Evipan
  • Hexabarbital
  • Hexanastab oral
  • Hexenal
  • Hexenal (barbiturate)
  • Hexobarbital
  • Hexobarbital (VAN)
  • Hexobarbitalum
  • Hexobarbitalum [INN-Latin]
  • Hexobarbitone
  • Hexobarbitonum
  • Methexenyl
  • Methylhexabarbital
  • Methylhexabital
  • N-Methyl-5-cyclohexenyl-5-methylbarbituric acid
  • Narcosan
  • Noctivane
  • NSC 71929
  • Sombucaps
  • Sombulex
  • Somnalert
  • UNII-AL8Z8K3P6S

Systematic Names

  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-
  • Barbituric acid, 5-(1-cyclohexen-1-yl)-1,5-dimethyl-
  • Hexobarbital

Registry Numbers

CAS Registry Number

  • 56-29-1

FDA UNII

  • AL8Z8K3P6S

Other Registry Numbers

  • 630-97-7
  • 7200-11-5

System Generated Number

  • 0000056291

Structure Descriptors

InChI

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

InChIKey

UYXAWHWODHRRMR-UHFFFAOYSA-N

Smiles

C=1([C@@]2(C(N(C(O)=NC2=O)C)=O)C)CCCCC1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LD50 parenteral 148mg/kg (148mg/kg)   Pharmacology and Toxicology. English translation of FATOAO. Vol. 20, Pg. 569, 1957.
frog LDLo intraperitoneal 30mg/kg (30mg/kg)   Physiological Reviews. Vol. 19, Pg. 472, 1939.
mouse LD50 intraperitoneal 270mg/kg (270mg/kg)   Toxicology and Applied Pharmacology. Vol. 5, Pg. 790, 1963.
mouse LD50 intravenous 133mg/kg (133mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 163, Pg. 11, 1966.
mouse LD50 oral 468mg/kg (468mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 106, Pg. 444, 1952.
mouse LD50 parenteral 160mg/kg (160mg/kg)   Pharmacology and Toxicology. English translation of FATOAO. Vol. 20, Pg. 569, 1957.
mouse LDLo intrapleural 340mg/kg (340mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 134, Pg. 95, 1961.
mouse LDLo subcutaneous 250mg/kg (250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 688, 1965.
rabbit LDLo intravenous 80mg/kg (80mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 60, Pg. 189, 1937.
rabbit LDLo oral 1200mg/kg (1200mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 60, Pg. 189, 1937.
rabbit LDLo rectal 175mg/kg (175mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 60, Pg. 189, 1937.
rat LD50 intraperitoneal 330mg/kg (330mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 184, Pg. 5, 1970.
rat LDLo subcutaneous 400mg/kg (400mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 182, Pg. 348, 1936.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 146.5 deg C   EXP
pKa Dissociation Constant 8.2 (none)   EXP
log P (octanol-water) 1.98 (none)   EXP
Water Solubility 435 mg/L 25 EXP
Vapor Pressure 3.11E-11 mm Hg 25 EST
Henry's Law Constant 8.48E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.51E-11 cm3/molecule-sec 25 EST

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