Norketamine

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Norketamine
Norketamine.svg
Systematic (IUPAC) name
2-Amino-2-(2-chlorophenyl)cyclohexan-1-one
Identifiers
CAS Number 35211-10-0
79499-59-5 (HCl)
ATC code None
PubChem CID: 123767
ChemSpider 110322
ChEMBL CHEMBL1039
Chemical data
Formula C12H14ClNO
Molecular mass 223.69866 g/mol
  • C1CCC(C(=O)C1)(C2=CC=CC=C2Cl)N
  • InChI=1S/C12H14ClNO/c13-10-6-2-1-5-9(10)12(14)8-4-3-7-11(12)15/h1-2,5-6H,3-4,7-8,14H2
  • Key:BEQZHFIKTBVCAU-UHFFFAOYSA-N

Norketamine, or N-desmethylketamine, is the major active metabolite of ketamine, which is formed mainly by CYP3A4.[1][2] Similarly to ketamine, norketamine acts as a noncompetitive NMDA receptor antagonist (Ki = 1.7 µM and 13 µM for (S)-(+)-norketamine and (R)-(–)-norketamine, respectively),[1][3] but is about 3–5 times less potent as an anesthetic in comparison.[2][4] Also, similarly again to ketamine, norketamine binds to the μ- and κ-opioid receptors.[5] Relative to ketamine, norketamine is much more potent as an antagonist of the α7-nicotinic acetylcholine receptor, and produces rapid antidepressant effects in animal models which have been reported to correlate with its activity at this receptor.[6] However, norketamine is about 1/5th as potent as ketamine as an antidepressant in mice as per the forced swim test, and this seems also to be in accordance with its 3–5-fold reduced comparative potency in vivo as an NMDA receptor antagonist.[7] Norketamine is metabolized into dehydronorketamine and hydroxynorketamine, which are far less or negligibly active as NMDA receptor antagonists in comparison[2] but retain activity as potent antagonists of the α7-nicotinic acetylcholine receptor.[8][9]

See also

References

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