CHEBI:60799 - esketamine

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ChEBI Name esketamine
ChEBI ID CHEBI:60799
Definition The S- (more active) enantiomer of ketamine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
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/t13-/m0/s1
InChIKey YQEZLKZALYSWHR-ZDUSSCGKSA-N
SMILES CN[C@@]1(CCCCC1=O)c1ccccc1Cl
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
(via ketamine )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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.
(via ketamine )
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.
(via ketamine )
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.
(via ketamine )
neurotoxin
A poison that interferes with the functions of the nervous system.
(via ketamine )
Application(s): 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.
(via ketamine )
intravenous anaesthetic

(via ketamine )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing esketamine (CHEBI:60799) has role analgesic (CHEBI:35480)
esketamine (CHEBI:60799) has role intravenous anaesthetic (CHEBI:38877)
esketamine (CHEBI:60799) has role NMDA receptor antagonist (CHEBI:60643)
esketamine (CHEBI:60799) is a ketamine (CHEBI:6121)
esketamine (CHEBI:60799) is enantiomer of (R)-ketamine (CHEBI:580604)
Incoming esketamine hydrochloride (CHEBI:60800) has part esketamine (CHEBI:60799)
(R)-ketamine (CHEBI:580604) is enantiomer of esketamine (CHEBI:60799)
IUPAC Name
(2S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone
INN Source
esketamine ChemIDplus
Synonyms Sources
(−)-ketamine ChemIDplus
(S)-(−)-ketamine ChemIDplus
(S)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone ChemIDplus
(S)-ketamine ChemIDplus
Manual Xrefs Databases
4468 DrugCentral
D07283 KEGG DRUG
DB01221 DrugBank
View more database links
Registry Numbers Types Sources
33643-46-8 CAS Registry Number ChemIDplus
33643-46-8 CAS Registry Number KEGG DRUG
4295313 Reaxys Registry Number Reaxys
Last Modified
22 February 2017
General Comment
2010-12-10 Ketamine is a rapid-acting general anaesthetic which, unlike other general anaesthetic agents, does not interact with GABA receptors. Esketamine, the (S)-enantiomer, has 3-4 times more anaesthetic potency than the (R)-enantiomer. Administered as the hydrochloride by intravenous or intramuscular injection it produces dissociative anaesthesia characterised by profound analgesia, amnesia, and a trance-like state. 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. Note that while (S)-ketamine is levorotatory (−), its hydrochloride salt is dextrorotatory (+).