Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Amobarbital [USP:INN:BAN:JAN]
RN: 57-43-2
UNII: GWH6IJ239E
InChIKey: VIROVYVQCGLCII-UHFFFAOYSA-N

Note

  • A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565)

Molecular Formula

  • C11-H18-N2-O3

Molecular Weight

  • 226.274
 

Classification Codes

Classification Codes

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

Superlist Classification Codes

  • DEA Schedule II
  • DEA Schedule III
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

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

MeSH Heading

  • Amobarbital

Synonyms

  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(3-methylbutyl)-
  • 5-Ethyl-5-(3-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
  • 5-Ethyl-5-(3-methylbutyl)barbituric acid
  • 5-Ethyl-5-isoamylbarbituric acid
  • 5-Ethyl-5-isoamylmalonyl urea
  • 5-Ethyl-5-isopentylbarbituric acid
  • 5-Ethyl-5-isopentylbarbitursaeure
  • 5-Isoamyl-5-ethylbarbituric acid
  • AMAL
  • Amasust
  • Amital
  • Amobarbital
  • Amobarbitale
  • Amobarbitale [DCIT]
  • Amobarbitalum
  • Amobarbitalum [INN-Latin]
  • Amobarbitone
  • Amospan
  • Amybal
  • Amylbarbitone
  • Amylobarbital
  • Amylobarbitone
  • Amytal
  • Barbamil
  • Barbamyl
  • Barbamyl acid
  • Barbituric acid, 5-ethyl-5-isopentyl-
  • Binoctal
  • CCRIS 5454
  • Dorlotyn
  • Dormytal
  • EINECS 200-330-7
  • Ethylisopentylbarbituric acid
  • Eunoctal
  • HSDB 3286
  • Isoamylethylbarbituric acid
  • Isomyl
  • Isomytal
  • Mylodorm
  • NSC 10815
  • Pentymal
  • Pentymalum
  • Robarb
  • Schiwanox
  • Sednotic
  • Somnal
  • Stadadorm
  • Sumital
  • Talamo
  • UNII-GWH6IJ239E

Systematic Names

  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(3-methylbutyl)-
  • Amobarbital
  • Barbituric acid, 5-ethyl-5-isopentyl-

Superlist Names

  • Amobarbital
  • Amobarbital suppository dosage form
  • DEA No. 2125

Mixture Name

  • Dexamyl

Registry Numbers

CAS Registry Number

  • 57-43-2

FDA UNII

  • GWH6IJ239E

Related Registry Number

  • 64-43-7 (hydrochloride)

System Generated Number

  • 0000057432

Structure Descriptors

InChI

1S/C11H18N2O3/c1-4-11(6-5-7(2)3)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)

InChIKey

VIROVYVQCGLCII-UHFFFAOYSA-N

Smiles

C1(C(NC(=O)NC1=O)=O)(CCC(C)C)CC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 100mg/kg (100mg/kg)   Physiological Reviews. Vol. 19, Pg. 472, 1939.
dog LD50 intravenous 58mg/kg (58mg/kg)   Drugs in Japan Vol. -, Pg. 63, 1990.
dog LDLo oral 250mg/kg (250mg/kg) BEHAVIORAL: SLEEP Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 371, 1926.
mammal (species unspecified) LDLo oral 550mg/kg (550mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 42, Pg. 253, 1931.
mouse LD50 intraperitoneal 175mg/kg (175mg/kg) BEHAVIORAL: GENERAL ANESTHETIC Journal of Medicinal Chemistry. Vol. 10, Pg. 1078, 1967.
mouse LD50 oral 345mg/kg (345mg/kg)   Journal of the American Chemical Society. Vol. 61, Pg. 96, 1939.
mouse LD50 subcutaneous 212mg/kg (212mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 688, 1965.
rabbit LD50 intravenous 49mg/kg (49mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 96, Pg. 209, 1949.
rabbit LD50 oral 575mg/kg (575mg/kg)   Drugs in Japan Vol. -, Pg. 63, 1990.
rabbit LDLo intraperitoneal 90mg/kg (90mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 41, Pg. 465, 1931.
rabbit LDLo subcutaneous 170mg/kg (170mg/kg)   Journal of the American Chemical Society. Vol. 45, Pg. 243, 1923.
rat LD50 intraperitoneal 115mg/kg (115mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 719, 1971.
rat LD50 oral 250mg/kg (250mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 719, 1971.
rat LD50 subcutaneous 190mg/kg (190mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 152, Pg. 341, 1930.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 157 deg C   EXP
pKa Dissociation Constant 7.84 (none)   EXP
log P (octanol-water) 2.07 (none)   EXP
Water Solubility 603 mg/L 25 EXP
Vapor Pressure 2.17E-11 mm Hg 25 EST
Henry's Law Constant 8.44E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.44E-11 cm3/molecule-sec 25 EST

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