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Substance Name: Pentobarbital [USP:INN:BAN]
RN: 76-74-4
UNII: I4744080IR
InChIKey: WEXRUCMBJFQVBZ-UHFFFAOYSA-N

Note

  • A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236)

Molecular Formula

  • C11-H18-N2-O3

Molecular Weight

  • 226.2742
 

Classification Codes

Classification Codes

  • Adjuvants, Anesthesia
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • GABA Agents
  • GABA Modulators
  • Human Data
  • Hypnotics and Sedatives
  • Neurotransmitter Agents
  • Reproductive Effect
  • Sedative-Hypnotic

Superlist Classification Code

  • DEA Schedule II

Names and Synonyms

Name of Substance

  • Pentobarbital
  • Pentobarbital [USP:INN:BAN]

MeSH Heading

  • Pentobarbital

Synonyms

  • (+-)-5-Ethyl-5-(1-methylbutyl)barbituric acid
  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylbutyl)-
  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylbutyl)-, (+-)-
  • 5-24-09-00168 (Beilstein Handbook Reference)
  • 5-Ethyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
  • 5-Ethyl-5-(1-methylbutyl)barbituric acid
  • 5-Ethyl-5-(1-methylbutyl)malonylurea
  • 5-Ethyl-5-(sec-pentyl)barbituric acid
  • Aethaminalum
  • Barbituric acid, 5-ethyl-5-(2-pentyl)-
  • BRN 0087067
  • CCRIS 7089
  • Dorsital
  • EC 200-983-8
  • EINECS 200-983-8
  • Ethaminal
  • Ethyl-propylmethylcarbinylbarbituric acid
  • HSDB 3151
  • Mebubarbital
  • Mebumal
  • Nebralin
  • Nembutal
  • Nembutal (VAN)
  • Neodorm
  • Neodorm (new)
  • Neodorm (VAN)
  • NSC 28708
  • Pentobarbital
  • Pentobarbital (VAN)
  • Pentobarbitale
  • Pentobarbitale [DCIT]
  • Pentobarbitalum
  • Pentobarbitalum [INN-Latin]
  • Pentobarbitone
  • Pentobarbitone (VAN)
  • Pentobarbiturate
  • Pentobarbituric acid
  • Phenobarbitone
  • Rivadorm
  • Sagatal
  • UNII-I4744080IR

Systematic Names

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

Registry Numbers

CAS Registry Number

  • 76-74-4

FDA UNII

  • I4744080IR

Related Registry Number

  • 57-33-0 (mono-hydrochloride salt)

System Generated Number

  • 0000076744

Structure Descriptors

InChI

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

InChIKey

WEXRUCMBJFQVBZ-UHFFFAOYSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 72mg/kg (72mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 28, Pg. 1479, 1969.
dog LD50 intravenous 50mg/kg (50mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Archives Internationales de Pharmacodynamie et de Therapie. Vol. 141, Pg. 83, 1963.
human LDLo oral 36mg/kg (36mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA Clinical Toxicology. Vol. 10, Pg. 327, 1977.
mouse LD50 intraperitoneal 75mg/kg (75mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 181, Pg. 68, 1969.
mouse LD50 intravenous 65mg/kg (65mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Archives Internationales de Pharmacodynamie et de Therapie. Vol. 141, Pg. 83, 1963.
mouse LD50 oral 170mg/kg (170mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 118, Pg. 139, 1956.
rabbit LD50 intravenous 33mg/kg (33mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 96, Pg. 209, 1949.
rabbit LDLo intraperitoneal 65mg/kg (65mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 44, Pg. 325, 1932.
rabbit LDLo oral 175mg/kg (175mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 44, Pg. 325, 1932.
rat LD50 intraperitoneal 108mg/kg (108mg/kg)   Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 19, Pg. 182, 1979.
rat LD50 oral 125mg/kg (125mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 7, Pg. 262, 1948.
rat LD50 subcutaneous 144mg/kg (144mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 118, Pg. 139, 1956.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 129.5 deg C   EXP
pKa Dissociation Constant 8.11 (none) 25 EXP
log P (octanol-water) 2.1 (none)   EXP
Water Solubility 679 mg/L 25 EXP
Vapor Pressure 3.02E-10 mm Hg 25 EST
Henry's Law Constant 8.44E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.80E-11 cm3/molecule-sec 25 EST

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