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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-10-23 19:06:30 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
Thumb
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
(-)-KetamineHMDB
(S)-(-)-KetamineHMDB
(S)-KetamineHMDB
CI 581 baseHMDB
Ketamine baseHMDB
Ketamine HCLHMDB
L-KetamineHMDB
2-(2-Chlorophenyl)-2-(methylamino)cyclohexanoneMeSH
CalypsolMeSH
KetanestMeSH
CalipsolMeSH
KalipsolMeSH
KetalarMeSH
Ketamine hydrochlorideMeSH
KetasetMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
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:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Psychiatric disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point92.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.046 g/LNot Available
LogP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP2.69ALOGPS
logP3.35ChemAxon
logS-3.7ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-1900000000-137b9855ffed670aa9f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0930000000-8216e02922628a5070cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0090000000-7704dbbfa717abc4bab2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-aff2b684d97275321043View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0290000000-1707dec51cc3e89964c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0940000000-59871faec16835eb1b3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-ca62e82b4a1dfb81b3b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-6c243d7b1c2e8cf69efaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-441a423105753e2c8b9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-24585e7c2431b3b9319eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0290000000-c9d734b085ec94dabd9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0940000000-054d77385726d4e35e20View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-8c263bb521fb6ebe6cacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-702873d66ce0d419711dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-e23ba411aa96df9b5d6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0090000000-5f14196db213c95f3e71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0090000000-85385cf96aa2ac05921aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05br-0390000000-9177663a5915fac51aa7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0910000000-d00d242dae695dc5aff9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0900000000-95c2a8805f1587266feaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-d3addd1c61dae1965d68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2490000000-4b32229520af03c01035View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy0-3900000000-f31baf727a934e3e0c6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-3166c540bb2a7f57489eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0390000000-f6a156602d423ed34dc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-8920000000-d5d51aef2ac12188e9e8View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01221 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01221 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01221
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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 ]