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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:43:37 UTC
HMDB IDHMDB0015352
Secondary Accession Numbers
  • HMDB15352
Metabolite Identification
Common NameKetamine
DescriptionKetamine is only found in individuals that have used or taken this drug. It is a cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (receptors, N-methyl-D-aspartate) and may interact with sigma receptors. [PubChem]Ketamine has several clinically useful properties, including analgesia and less cardiorespiratory depressant effects than other anaesthetic agents, it also causes some stimulation of the cardiocascular system. Ketamine has been reported to produce general as well as local anaesthesia. It interacts with N-methyl-D-aspartate (NMDA) receptors, opioid receptors, monoaminergic receptors, muscarinic receptors and voltage sensitive Ca ion channels. Unlike other general anaesthetic agents, ketamine does not interact with GABA receptors.
Structure
Data?1582753287
Synonyms
ValueSource
(+-)-KetamineChEBI
2-(2-Chloro-phenyl)-2-methylamino-cyclohexanoneChEBI
2-(Methylamino)-2-(2-chlorophenyl)cyclohexanoneChEBI
2-(O-Chlorophenyl)-2-(methylamino)-cyclohexanoneChEBI
DL-KetamineChEBI
KetaminaChEBI
KetaminumChEBI
NMDAChEBI
Special KChEBI
TekamKegg
(-)-KetamineHMDB
(S)-(-)-KetamineHMDB
(S)-KetamineHMDB
CI 581 baseHMDB
Ketamine baseHMDB
Ketamine HCLHMDB
L-KetamineHMDB
2-(2-Chlorophenyl)-2-(methylamino)cyclohexanoneHMDB
CalypsolHMDB
KetanestHMDB
CalipsolHMDB
KalipsolHMDB
KetalarHMDB
Ketamine hydrochlorideHMDB
KetasetHMDB
Chemical FormulaC13H16ClNO
Average Molecular Weight237.725
Monoisotopic Molecular Weight237.092041846
IUPAC Name2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
Traditional Nameketamine
CAS Registry Number6740-88-1
SMILES
CNC1(CCCCC1=O)C1=CC=CC=C1Cl
InChI Identifier
InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3
InChI KeyYQEZLKZALYSWHR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Ketone
  • Cyclic ketone
  • Secondary aliphatic amine
  • Secondary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point92.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.046 g/LNot Available
LogP2.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM149.230932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP10(2.69) g/LALOGPS
logP10(3.35) g/LChemAxon
logS10(-3.7) g/LALOGPS
pKa (Strongest Acidic)18.78ChemAxon
pKa (Strongest Basic)7.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.55 m³·mol⁻¹ChemAxon
Polarizability24.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
KetamineCNC1(CCCCC1=O)C1=CC=CC=C1Cl2494.7Standard polar33892256
KetamineCNC1(CCCCC1=O)C1=CC=CC=C1Cl1851.4Standard non polar33892256
KetamineCNC1(CCCCC1=O)C1=CC=CC=C1Cl1836.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ketamine,1TMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C1902.6Semi standard non polar33892256
Ketamine,1TMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C1929.6Standard non polar33892256
Ketamine,1TMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C2394.0Standard polar33892256
Ketamine,1TMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C1921.1Semi standard non polar33892256
Ketamine,1TMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C1981.4Standard non polar33892256
Ketamine,1TMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C2413.3Standard polar33892256
Ketamine,2TMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C)[Si](C)(C)C1987.3Semi standard non polar33892256
Ketamine,2TMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C)[Si](C)(C)C1979.9Standard non polar33892256
Ketamine,2TMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C)[Si](C)(C)C2337.9Standard polar33892256
Ketamine,1TBDMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C2109.3Semi standard non polar33892256
Ketamine,1TBDMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C2099.0Standard non polar33892256
Ketamine,1TBDMS,isomer #1CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C2532.0Standard polar33892256
Ketamine,1TBDMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C(C)(C)C2168.3Semi standard non polar33892256
Ketamine,1TBDMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C(C)(C)C2239.4Standard non polar33892256
Ketamine,1TBDMS,isomer #2CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C(C)(C)C2528.8Standard polar33892256
Ketamine,2TBDMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2443.8Semi standard non polar33892256
Ketamine,2TBDMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2321.5Standard non polar33892256
Ketamine,2TBDMS,isomer #1CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2546.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ketamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-1900000000-137b9855ffed670aa9f42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ketamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ketamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-QTOF , positive-QTOFsplash10-004i-0930000000-8216e02922628a5070cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-00di-0090000000-7704dbbfa717abc4bab22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-aff2b684d972753210432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-000i-0290000000-1707dec51cc3e89964c92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-004i-0940000000-59871faec16835eb1b3a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-ca62e82b4a1dfb81b3b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-6c243d7b1c2e8cf69efa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-441a423105753e2c8b9c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-24585e7c2431b3b9319e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-000i-0290000000-c9d734b085ec94dabd9a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-004i-0940000000-054d77385726d4e35e202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-8c263bb521fb6ebe6cac2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-702873d66ce0d419711d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-e23ba411aa96df9b5d6f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOFsplash10-00di-0090000000-5f14196db213c95f3e712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-QQ , positive-QTOFsplash10-000i-0090000000-85385cf96aa2ac05921a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-QQ , positive-QTOFsplash10-05br-0390000000-9177663a5915fac51aa72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-QQ , positive-QTOFsplash10-004i-0910000000-d00d242dae695dc5aff92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ketamine LC-ESI-QQ , positive-QTOFsplash10-004i-0900000000-95c2a8805f1587266fea2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketamine 10V, Positive-QTOFsplash10-000i-0190000000-d3addd1c61dae1965d682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketamine 20V, Positive-QTOFsplash10-000i-2490000000-4b32229520af03c010352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketamine 40V, Positive-QTOFsplash10-0uy0-3900000000-f31baf727a934e3e0c6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketamine 10V, Negative-QTOFsplash10-000i-0090000000-3166c540bb2a7f57489e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketamine 20V, Negative-QTOFsplash10-000i-0390000000-f6a156602d423ed34dc12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ketamine 40V, Negative-QTOFsplash10-0229-8920000000-d5d51aef2ac12188e9e82016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01221 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01221 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01221
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3689
KEGG Compound IDC07525
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKetamine
METLIN IDNot Available
PubChem Compound3821
PDB IDNot Available
ChEBI ID6121
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. [PubMed:2858237 ]
  2. Reboso Morales JA, Gonzalez Miranda F: [Ketamine]. Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. [PubMed:10228376 ]
  3. Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. [PubMed:10551055 ]
  4. Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. [PubMed:12091028 ]
  5. Lankenau SE, Sanders B, Bloom JJ, Hathazi D, Alarcon E, Tortu S, Clatts MC: First injection of ketamine among young injection drug users (IDUs) in three U.S. cities. Drug Alcohol Depend. 2007 Mar 16;87(2-3):183-93. Epub 2006 Sep 18. [PubMed:16979848 ]