CHEBI:6121 - ketamine

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ChEBI Name ketamine
ChEBI ID CHEBI:6121
Definition A member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:138833
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Formula C13H16ClNO
Net Charge 0
Average Mass 237.72500
Monoisotopic Mass 237.09204
InChI 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
InChIKey YQEZLKZALYSWHR-UHFFFAOYSA-N
SMILES CNC1(CCCCC1=O)c1ccccc1Cl
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): NMDA receptor antagonist
Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
neurotoxin
A poison that interferes with the functions of the nervous system.
Application(s): intravenous anaesthetic

analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ketamine (CHEBI:6121) has role analgesic (CHEBI:35480)
ketamine (CHEBI:6121) has role environmental contaminant (CHEBI:78298)
ketamine (CHEBI:6121) has role intravenous anaesthetic (CHEBI:38877)
ketamine (CHEBI:6121) has role neurotoxin (CHEBI:50910)
ketamine (CHEBI:6121) has role NMDA receptor antagonist (CHEBI:60643)
ketamine (CHEBI:6121) has role xenobiotic (CHEBI:35703)
ketamine (CHEBI:6121) is a cyclohexanones (CHEBI:23482)
ketamine (CHEBI:6121) is a monochlorobenzenes (CHEBI:83403)
ketamine (CHEBI:6121) is a secondary amino compound (CHEBI:50995)
Incoming ketamine hydrochloride (CHEBI:650657) has part ketamine (CHEBI:6121)
(R)-ketamine (CHEBI:580604) is a ketamine (CHEBI:6121)
esketamine (CHEBI:60799) is a ketamine (CHEBI:6121)
IUPAC Name
2-(2-chlorophenyl)-2-(methylamino)cyclohexanone
INNs Sources
ketamina WHO MedNet
ketamine ChemIDplus
kétamine WHO MedNet
ketaminum ChemIDplus
Synonyms Sources
(±)-ketamine ChemIDplus
2-(2-Chloro-phenyl)-2-methylamino-cyclohexanone ChEMBL
2-(methylamino)-2-(2-chlorophenyl)cyclohexanone ChemIDplus
2-(o-chlorophenyl)-2-(methylamino)-cyclohexanone ChemIDplus
dl-ketamine ChemIDplus
DL-ketamine ChEBI
KETAMINE ChEMBL
Ketamine KEGG COMPOUND
NMDA ChEBI
special K ChemIDplus
Manual Xrefs Databases
1523 DrugCentral
2978 VSDB
BE634208 Patent
C07525 KEGG COMPOUND
D08098 KEGG DRUG
DB01221 DrugBank
HMDB0015352 HMDB
Ketamine Wikipedia
US3254124 Patent
View more database links
Registry Numbers Types Sources
100477-72-3 CAS Registry Number NIST Chemistry WebBook
2216965 Reaxys Registry Number Reaxys
6740-88-1 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
3783598 PubMed citation ChEMBL
Last Modified
22 February 2017
General Comment
2010-12-10 Ketamine is a rapid-acting general anaesthetic administered as the hydrochloride by intravenous or intramuscular injection and producing dissociative anaesthesia characterised by profound analgesia, amnesia, and a trance-like state. The (S)-enantiomer has 3-4 times more anaesthetic potency than the (R)-enantiomer. Unlike other general anaesthetic agents, ketamine does not interact with GABA receptors. It is used for diagnostic or short surgical operations not requiring skeletal muscle relaxation, and for induction of anaesthesia which is then maintained with other drugs. It also has good analgesic properties when used in subanaesthetic doses.