You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:32:33 UTC
HMDB IDHMDB15352
Secondary Accession NumbersNone
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
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 KeyInChIKey=YQEZLKZALYSWHR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chlorobenzenes. These 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
  • Aralkylamine
  • Cyclohexylamine
  • Cyclohexanone
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Cyclic ketone
  • Ketone
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Analgesics
  • Anesthetics, Dissociative
  • Excitatory Amino Acid Antagonists
  • General Anesthetics
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point92.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.64e-02 g/LNot Available
LogP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.55 m3·mol-1ChemAxon
Polarizability24.97 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01221
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01221
  • Not Applicable
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
NuGOwiki LinkHMDB15352
Metagene LinkHMDB15352
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. [2858237 ]
  2. Reboso Morales JA, Gonzalez Miranda F: [Ketamine]. Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. [10228376 ]
  3. Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. [10551055 ]
  4. Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. [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. [16979848 ]