Secobarbital (CHEM002190)

Record Information
Version1.0
Creation Date2009-07-21 20:26:51 UTC
Update Date2026-05-14 16:38:11 UTC
Accession NumberCHEM002190
Identification
Common NameSecobarbital
ClassSmall Molecule
Description
Secobarbital is only found in individuals that have used or taken this drug. It is a barbiturate derivative drug. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone. Secobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Adjuvant
  • Adjuvant, Anesthesia
  • Amide
  • Amine
  • Barbiturate
  • Drug
  • GABA Modulator
  • Human Neurotoxin
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-SecobarbitalChEBI
5-(1-Methylbutyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Allyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Allyl-5-(1-methylbutyl)barbituric acidChEBI
5-Allyl-5-(1-methylbutyl)pyrimidine-2,4,6(1H,3H,5H)-trioneChEBI
QuinalbarbitoneChEBI
SecobarbitalumChEBI
SecobarbitoneChEBI
SeconalChEBI
5-Allyl-5-(1-methylbutyl)barbitateGenerator
5-Allyl-5-(1-methylbutyl)barbitic acidGenerator
(+/-)-secobarbitalHMDB
SecobarbitaleHMDB
Sodium quinalbarbitoneHMDB
Sodium secobarbitalHMDB
Ranbaxy brand OF secobarbital sodiumHMDB
Secobarbital sodiumHMDB
Vangard brand OF secobarbital sodiumHMDB
Seconal sodiumHMDB
Sodium, secobarbitalHMDB
MeballymalHMDB
SebarHMDB
Flynn brand OF secobarbital sodiumHMDB
Chemical FormulaC12H18N2O3
Average Molecular Mass238.283 g/mol
Monoisotopic Mass238.132 g/mol
CAS Registry Number76-73-3
IUPAC Name5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
Traditional Namesecobarbital
SMILESCCCC(C)C1(CC=C)C(=O)NC(=O)NC1=O
InChI IdentifierInChI=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)
InChI KeyKQPKPCNLIDLUMF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentBarbituric acid derivatives
Alternative Parents
Substituents
  • Barbiturate
  • N-acyl urea
  • Ureide
  • 1,3-diazinane
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point100°C
Boiling PointNot Available
Solubility550 mg/L
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP2.2ALOGPS
logP2.03ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)7.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.65 m³·mol⁻¹ChemAxon
Polarizability24.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (1); Parenteral (1); Rectal (1).
Mechanism of ToxicitySecobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Metabolism Route of Elimination: Barbiturates are metabolized primarily by the hepatic microsomal enzyme system, and the metabolic products are excreted in the urine and, less commonly, in the feces.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the Short-term treatment of intractable insomnia for patients habituated to barbiturates
Minimum Risk LevelNot Available
Health EffectsSecobarbital causes slurred speech, disorientation and "drunken" behavior. It is physically and psychologically addictive.
SymptomsSymptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00418
HMDB IDHMDB0014562
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSecobarbital
Chemspider ID5005
ChEBI ID9073
PubChem Compound ID5193
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References