Ketamine
Chemistry
- Formula
- C13H16ClNO
- Molar mass
- 237.72 g/mol
- IUPAC name
- 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
- InChIKey
- YQEZLKZALYSWHR-UHFFFAOYSA-N
Chemistry from PubChem CID 3821.
Also known as
- dl-Ketamine
- Ketaject
- Special K
- (+-)-Ketamine
- CI 581 base
- Ketaminum
- 6740-88-1
- CLSTA 20
Stereoisomers
2 distinct stereoisomers are registered for this structure. This area's record is the racemate — the mixture, which is normally the form encountered.
- Racemic ketamine this area mixture CID 3821
The standard anaesthetic and the usual clinic infusion.
- Esketamine — (S)-ketamine CID 182137
The more potent NMDA binder; the licensed nasal spray for treatment-resistant depression.
- Arketamine — (R)-ketamine CID 644025
Less potent as an anaesthetic; studied for psychiatric effects, not marketed.
Ketamine has two mirror-image forms, (S)-ketamine (esketamine) and (R)-ketamine (arketamine). What is sold and administered as "ketamine" is almost always the racemate — a 50/50 mixture — which has been the standard anaesthetic for decades and is what most infusion clinics use. Esketamine binds the NMDA receptor more strongly and is the basis of the patented nasal spray licensed for treatment-resistant depression. Arketamine is a research interest, not a marketed product.
Attribution
- Calvin L. Stevens — first synthesis, 1962
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