Butabarbital (CHEM002149)

Record Information
Version1.0
Creation Date2009-07-21 20:26:21 UTC
Update Date2026-05-14 16:24:51 UTC
Accession NumberCHEM002149
Identification
Common NameButabarbital
ClassSmall Molecule
Description
Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Anti-Anxiety Agent
  • Barbiturate
  • Drug
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-Ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Ethyl-5-(1-methylpropyl)barbituric acidChEBI
5-Sec-butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Sec-butyl-5-ethylbarbituric acidChEBI
5-Sec-butyl-5-ethylpyrimidine-2,4,6(1H,3H,5H)-trioneChEBI
ButisolChEBI
SecbutabarbitalChEBI
5-Ethyl-5-(1-methylpropyl)barbitateGenerator
5-Ethyl-5-(1-methylpropyl)barbitic acidGenerator
5-Sec-butyl-5-ethylbarbitateGenerator
5-Sec-butyl-5-ethylbarbitic acidGenerator
ButabarbitoneHMDB
ButrateHMDB
SecbubarbitalHMDB
SecbutobarbitalHMDB
SecbutobarbitoneHMDB
Sodium butabarbitalHMDB
SecumalumHMDB
2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-, monosodium saltHMDB
Butisol sodiumHMDB
Wallace brand OF butabarbital sodiumHMDB
Butabarbital sodiumHMDB
Secbutabarbital sodiumHMDB
Halsey drug brand OF butabarbital sodiumHMDB
SarisolHMDB
Chemical FormulaC10H16N2O3
Average Molecular Mass212.246 g/mol
Monoisotopic Mass212.116 g/mol
CAS Registry Number125-40-6
IUPAC Name5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione
Traditional Namebutabarbital
SMILESCCC(C)C1(CC)C(=O)NC(=O)NC1=O
InChI IdentifierInChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)
InChI KeyZRIHAIZYIMGOAB-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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point166.5°C
Boiling PointNot Available
Solubility1360 mg/L
Predicted Properties
PropertyValueSource
Water Solubility1.39 g/LALOGPS
logP1.7ALOGPS
logP1.45ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.4 m³·mol⁻¹ChemAxon
Polarizability21.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityButabarbital 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. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.
Metabolism Route of Elimination: Barbiturates are metabolized primarily by the hepatic microsomal enzyme system, and most metabolic products are excreted in the urine.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUseful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures;
Minimum Risk LevelNot Available
Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
SymptomsSigns of overdose include confusion (severe), decrease in or loss of reflexes, drowsiness (severe), fever, irritability (continuing), low body temperature, poor judgment, shortness of breath or slow or troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness (severe).
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00237
HMDB IDHMDB0014382
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkButabarbital
Chemspider ID2385
ChEBI ID3228
PubChem Compound ID2479
Kegg Compound IDC07827
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References