Butethal (CHEM002390)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (10)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:47 UTC
Update Date2026-05-14 16:59:44 UTC
Accession NumberCHEM002390
Identification
Common NameButethal
ClassSmall Molecule
DescriptionButethal is only found in individuals that have used or taken this drug. It is a sedative and a hypnotic drug.Butethal 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.
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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
NeonalKegg
5-Butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneHMDB
5-Butyl-5-ethylbarbituric acidHMDB
5-Ethyl-5-butylbarbituric acidHMDB
5-Ethyl-5-N-butylbarbituric acidHMDB
ButabarbitolHMDB
ButobarbitalHMDB
ButobarbitalumHMDB
ButobarbitoneHMDB
ButobarbituralHMDB
Butyl,5-ethylbarbituric acidHMDB
SonerylHMDB
Butethal, monosodium saltHMDB
Butobarbital, sodium saltHMDB
ButethalKEGG
Chemical FormulaC10H16N2O3
Average Molecular Mass212.246 g/mol
Monoisotopic Mass212.116 g/mol
CAS Registry Number77-28-1
IUPAC Name5-butyl-5-ethyl-1,3-diazinane-2,4,6-trione
Traditional Namebutethal
SMILESCCCCC1(CC)C(=O)NC(=O)NC1=O
InChI IdentifierInChI=1S/C10H16N2O3/c1-3-5-6-10(4-2)7(13)11-9(15)12-8(10)14/h3-6H2,1-2H3,(H2,11,12,13,14,15)
InChI KeySTDBAQMTJLUMFW-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 DescriptorsNot Available
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 Point128.5°C
Boiling PointNot Available
Solubility4880 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility1.27 g/LALOGPS
logP1.65ALOGPS
logP1.61ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.45 m³·mol⁻¹ChemAxon
Polarizability21.62 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9600000000-eef99ddbb9fc48cf8ed4Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-03di-0090000000-3021b7118b324b8467bdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9600000000-eef99ddbb9fc48cf8ed4Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-03di-0090000000-3021b7118b324b8467bdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ru-8900000000-4af4f13ca7ae2bc7fcdaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1390000000-43ecd68f229c3c3bc90cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-4900000000-1b15cbf105e1de888220Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-205e856802a03c319f4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0296-7940000000-170e8b066d6c58e18aceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9500000000-aa05ed5e0280f5ac92f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-8169dd5585539f0b6ae0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0920000000-404a31fe18ef594f21dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-3900000000-e48f90bfca377565c24eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9400000000-f5a557249efe744106d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-39954a7265a9cf3de21bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-6090000000-1346133bfd2e9697f150Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-b5bed8f717a537bd2583Spectrum
Toxicity Profile
Route of ExposureRapidly absorbed following oral administration. Parenteral (intraperitroneal injection or infusion).
Mechanism of ToxicityButethal 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.
MetabolismHepatic. Half Life: 37 hours
Toxicity ValuesLD50: 1.506 mM/kg (i.p., mice) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of insomnia.
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
DrugBank IDDB01353
HMDB IDHMDB0015442
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkButobarbital
Chemspider ID6229
ChEBI ID519412
PubChem Compound ID6473
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available