CH₃CH₃

Ketamine

Chemistry

32 atoms · Conformer computed and published by PubChem.
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.

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

    Sole named inventor on US 3,254,124 (filed 29 June 1962), which claims and exemplifies 2-methylamino-2-(o-chlorophenyl)cyclohexanone; ketamine is Example 15. Parke-Davis coded it CI-581. Stevens made the compound; the human pharmacology was Edward Domino and Guenter Corssen's work in 1964–65, and the term 'dissociative anaesthesia' came from that trial, not from him.

    source

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