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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:47:34 UTC
Update Date2019-07-23 06:35:13 UTC
HMDB IDHMDB0041913
Secondary Accession Numbers
  • HMDB41913
Metabolite Identification
Common NameKetobemidone
DescriptionKetobemidone (Cliradon, Ketogan, Ketodur, Cymidon, Ketorax, &c.) is a powerful opioid analgesic. Its effectiveness against pain is in the same range as morphine, and it also has some NMDA-antagonist properties imparted by its metabolite norketobemidone. This makes it useful for some types of pain that don't respond well to other opioids. The most commonly cited equalisation ratio for analgesic doses is 25 mg of ketobemidone hydrobromide to 60 mg of morphine hydrochloride or sulfate and circa 8 mg of ketobemidone by injection. Ketobemidone is 1-methyl-4-(3-hydroxyphenyl)-4-propionylpiperidine. It is usually available as the hydrochloride, which is a white powder. It is synthesized by alkylating (3-methoxyphenyl)acetonitrile with bis(2-chloroethyl)methylamine, followed by reaction with ethylmagnesiumbromide, and finally O-demethylation with hydrobromic acid.
Structure
Data?1563863713
Synonyms
ValueSource
KetodurHMDB
CetobemidoneHMDB
CliradonHMDB
KetoganHMDB
CymidonHMDB
KetoraxHMDB
1-(4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl)-1-propanoneHMDB
1-[4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanoneHMDB
4-(m-Hydroxyphenyl)-1-methyl-4-piperidyl ethyl ketoneHMDB
4-(m-Hydroxyphenyl)-1-methyl-4-propionylpiperidineHMDB
a 21 LundbeckHMDB
CetobemidonHMDB
CliradoneHMDB
Ethyl (4-(m-hydroxyphenyl)-1-methyl)-4-piperidyl ketoneHMDB
Ethyl {[4-(m-hydroxyphenyl)-1-methyl]-4-piperidyl} ketoneHMDB
Ketone, ethyl 4-(m-hydroxyphenyl)-1-methylpiperidylHMDB
{1-[4-(m-hydroxyphenyl)-1-methyl-4-piperidyl]-1-propanone}HMDB
Ketobemidone hydrochlorideMeSH
Chemical FormulaC15H21NO2
Average Molecular Weight247.3327
Monoisotopic Molecular Weight247.157228921
IUPAC Name1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one
Traditional Nameketobemidone
CAS Registry Number469-79-4
SMILES
CCC(=O)C1(CCN(C)CC1)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C15H21NO2/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3
InChI KeyALFGKMXHOUSVAD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Gamma-aminoketone
  • Benzenoid
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point156.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.01 g/LALOGPS
logP2.01ALOGPS
logP2.49ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.44ChemAxon
pKa (Strongest Basic)8.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.12 m³·mol⁻¹ChemAxon
Polarizability28.09 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3910000000-6decb78c046347ae40f5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-3091000000-0cf23890669092455f92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-b0eb6846d8434b71e163Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2390000000-41423312ecf719c689d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-074m-5910000000-e7966d50007a351d14e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-18564889dbd2dc37a407Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2190000000-015e225df40c337cafe3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-8940000000-c9ccc1d7e952deff9332Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDBSALT000189
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9697
KEGG Compound IDC11792
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKetobemidone
METLIN IDNot Available
PubChem Compound10101
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available