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Substance Name: Secobarbital [USP:INN]
RN: 76-73-3
UNII: 1P7H87IN75
InChIKey: KQPKPCNLIDLUMF-UHFFFAOYSA-N

Note

  • A barbiturate that is used as a sedative. Secobarbital is reported to have no anti-anxiety activity.

Molecular Formula

  • C12-H18-N2-O3

Molecular Weight

  • 238.285
 

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
  • Sedative-Hypnotic
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Names and Synonyms

Name of Substance

  • Secobarbital
  • Secobarbital [USP:INN]

MeSH Heading

  • Secobarbital

Synonyms

  • (+-)-5-Allyl-5-(1-methylbutyl)-barbituric acid
  • (+-)-Secobarbital
  • 5-24-09-00235 (Beilstein Handbook Reference)
  • 5-Allyl-5-(1-methylbutyl)barbiturate
  • 5-Allyl-5-(1-methylbutyl)barbituric acid
  • 5-Allyl-5-(1-methylbutyl)malonylurea
  • Barbituric acid, 5-allyl-5-(1-methylbutyl)-
  • Barbosec
  • BRN 0225330
  • EINECS 200-982-2
  • Evronal
  • HSDB 3182
  • Hypotrol
  • Meballymal
  • Meballymalum
  • Pramil
  • Quinalbarbital
  • Quinalbarbitone
  • Secobarbital
  • Secobarbitale
  • Secobarbitale [DCIT]
  • Secobarbitalum
  • Secobarbitalum [INN-Latin]
  • Secobarbitone
  • Seconal
  • Seotal
  • Somosal
  • UNII-1P7H87IN75

Systematic Names

  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propenyl)-
  • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propenyl)-, (+-)-
  • Barbituric acid, 5-allyl-5-(1-methylbutyl)-
  • Barbituric acid, 5-allyl-5-(1-methylbutyl)-, (+-)-
  • Secobarbital

Superlist Names

  • DEA No. 2315
  • Secobarbital
  • Secobarbital suppository dosage form
  • Secobarbital suppository dosage form [DEA No. 2316]

Mixture Name

  • Hyptran

Registry Numbers

CAS Registry Number

  • 76-73-3

FDA UNII

  • 1P7H87IN75

Other Registry Number

  • 29071-21-4

System Generated Number

  • 0000076733

Structure Descriptors

InChI

InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)

InChIKey

KQPKPCNLIDLUMF-UHFFFAOYSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intraperitoneal 75mg/kg (75mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
cat LDLo intravenous 50mg/kg (50mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
dog LDLo oral 90mg/kg (90mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
frog LDLo oral 90mg/kg (90mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
guinea pig LDLo intraperitoneal 40mg/kg (40mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
guinea pig LDLo intravenous 35mg/kg (35mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
guinea pig LDLo subcutaneous 60mg/kg (60mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
human LDLo oral 33mg/kg (33mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA Clinical Toxicology. Vol. 10, Pg. 327, 1977.
mouse LD50 intraperitoneal 116mg/kg (116mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 65, 1959.
mouse LD50 oral 145mg/kg (145mg/kg)   Journal of Ethnopharmacology. Vol. 27, Pg. 213, 1989.
mouse LDLo intravenous 130mg/kg (130mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
mouse LDLo subcutaneous 160mg/kg (160mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
rabbit LDLo intraperitoneal 50mg/kg (50mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
rabbit LDLo intravenous 45mg/kg (45mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
rabbit LDLo subcutaneous 90mg/kg (90mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
rat LD50 intravenous 80mg/kg (80mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
rat LDLo intraperitoneal 110mg/kg (110mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
rat LDLo oral 125mg/kg (125mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
rat LDLo subcutaneous 140mg/kg (140mg/kg)   Journal of the American Pharmaceutical Association. Vol. 26, Pg. 1248, 1937.
women TDLo oral 32mg/kg (32mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: COMA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 British Medical Journal. Vol. 1, Pg. 1238, 1955.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 100 deg C   EXP
pKa Dissociation Constant 7.8 (none)   EXP
log P (octanol-water) 1.97 (none)   EXP
Water Solubility 550 mg/L 25 EST
Vapor Pressure 3.36E-10 mm Hg 25 EST
Henry's Law Constant 8.35E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.41E-11 cm3/molecule-sec 25 EST

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