Methohexital (T3D2803)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-21 20:26:59 UTC
Update Date2014-12-24 20:25:51 UTC
Accession NumberT3D2803
Identification
Common NameMethohexital
ClassSmall Molecule
DescriptionMethohexital is only found in individuals that have used or taken this drug. It is an intravenous anesthetic with a short duration of action that may be used for induction of anesthesia. Methohexital 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.
Compound Type
  • Amide
  • Amine
  • Anesthetic
  • Anesthetic, Intravenous
  • Barbiturate
  • Drug
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(+-)-5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)barbituric acid
5-Allyl-1-methyl-5-(1-methyl-2-pentynyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
5-Allyl-1-methyl-5-(1-methyl-pent-2-ynyl)-pyrimidine-2,4,6-trione
5-Allyl-5-(3-hexyn-2-yl)-1-methylbarbituric acid
alpha-DL-1-Methyl-5-allyl-5-(1'-methylpentyn-2-yl)barbituric acid
Brevital
Brietal
Methodrexitone
Methohexitalum
Methohexitone
Metohexital
Chemical FormulaC14H18N2O3
Average Molecular Mass262.304 g/mol
Monoisotopic Mass262.132 g/mol
CAS Registry Number151-83-7
IUPAC Name5-(hex-3-yn-2-yl)-1-methyl-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
Traditional Namemethohexital
SMILESCCC#CC(C)C1(CC=C)C(O)=NC(=O)N(C)C1=O
InChI IdentifierInChI=1/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)
InChI KeyInChIKey=NZXKDOXHBHYTKP-UHFFFAOYNA-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 RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility5.24e-02 g/L
LogP1.8
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP2.43ALOGPS
logP2.29ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity71.51 m³·mol⁻¹ChemAxon
Polarizability27.4 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-4390000000-8c577a429e1b4575b6292017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00ya-3900000000-577a972e968dc27cf6a62021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2090000000-43730b3bde391b731ebe2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-3970000000-fc9a91490da8afc576f02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9x-9000000000-93587b41eae6b9864e812016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2920000000-ad50a444d0a4a9a5af2c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-4910000000-c5dc261173ac7024e26f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-7cedeac5d5e1a5954aa42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-c3de47045d3b9ea5dd1f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-4890000000-e57232418c552e436a952021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015c-3910000000-34338787c291ec35bb4c2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-859e807fb540e8aaf0912021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0910000000-70fde9c253e18d4487912021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9300000000-67ceed0497570d0689e32021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fbc-9520000000-5141cdceea7f6d5013b02014-09-20View Spectrum
Toxicity Profile
Route of ExposureParenteral (intramuscular, intravenous). The absolute bioavailability following rectal administration of methohexital is 17%.
Mechanism of ToxicityMethohexital 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.
MetabolismMetabolism occurs in the liver through demethylation and oxidation. Side-chain oxidation is the most important biotransformation involved in termination of biologic activity. Route of Elimination: Excretion occurs via the kidneys through glomerular filtration. Half Life: 5.6 ± 2.7 minutes
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMethohexital is indicated for use as an intravenous anaesthetic. It has also been commonly used to induce deep sedation. It is only used in hospital or similar settings, under strict supervision.
Minimum Risk LevelNot Available
Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
SymptomsThe onset of toxicity following an overdose of intravenously administered methohexital will be within seconds of the infusion. If methohexital is administered rectally or is ingested, the onset of toxicity may be delayed. The manifestations of an ultrashort-acting barbiturate in overdose include central nervous system depression, respiratory depression, hypotension, loss of peripheral vascular resistance, and muscular hyperactivity ranging from twitching to convulsive-like movements. Other findings may include convulsions and allergic reactions.
TreatmentEstablish an airway and ensure oxygenation and ventilation. Resuscitative measures should be initiated promptly. For hypotension, intravenous fluids should be administered and the patient's legs raised. If desirable increase in blood pressure is not obtained, vasopressor and/or inotropic drugs may be used as dictated by the clinical situation. For convulsions, diazepam intravenously and phenytoin may be required. If the seizures are refractory to diazepam and phenytoin, general anesthesia and paralysis with a neuromuscular blocking agent may be necessary. Protect the patient's airway and support ventilation and perfusion. Meticulously monitor and maintain, within acceptable limits, the patient's vital signs, blood gases, serum electrolytes, etc. Absorption of drugs from the gastrointestinal tract may be decreased by giving activated charcoal, which, in many cases, is more effective than emesis or lavage; consider charcoal instead of or in addition to gastric emptying. Repeated doses of charcoal over time may hasten elimination of some drugs that have been absorbed. Safeguard the patient's airway when employing gastric emptying or charcoal. (3)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00474
HMDB IDHMDB14617
PubChem Compound ID9034
ChEMBL IDCHEMBL7413
ChemSpider ID8683
KEGG IDC07844
UniProt IDNot Available
OMIM ID
ChEBI ID102216
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMethohexital
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMethohexital
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Janssen PA, Niemegeers CJ, Marsboom RP: Etomidate, a potent non-barbiturate hypnotic. Intravenous etomidate in mice, rats, guinea-pigs, rabbits and dogs. Arch Int Pharmacodyn Ther. 1975 Mar;214(1):92 -132. [1156027 ]
  2. Drugs.com [Link]
  3. RxList: The Internet Drug Index (2009). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Gamma-aminobutyric acid receptor subunit alpha-1
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular Weight:
51801.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]