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Human drug metabolites
Dehydronorketamine
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    Dehydronorketamine

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    Dehydronorketamine
    5,6-Dehydronorketamine.svg
    Clinical data
    ATC code
    • None
    Identifiers
    • 6-Amino-6-(2-chlorophenyl)cyclohex-2-en-1-one
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C12H12ClNO
    Molar mass 221.68 g·mol−1
    3D model (JSmol)
    • C1CC(C(=O)C=C1)(C2=CC=CC=C2Cl)N
    • InChI=1S/C12H12ClNO/c13-10-6-2-1-5-9(10)12(14)8-4-3-7-11(12)15/h1-3,5-7H,4,8,14H2
    • Key:BXBPJMHHWPXBJL-UHFFFAOYSA-N

    Dehydronorketamine (DHNK), or 5,6-dehydronorketamine, is a minor metabolite of ketamine which is formed by dehydrogenation of its metabolite norketamine. Though originally considered to be inactive, DHNK has been found to act as a potent and selective negative allosteric modulator of the α7-nicotinic acetylcholine receptor (IC50 = 55 nM). For this reason, similarly to hydroxynorketamine (HNK), it has been hypothesized that DHNK may have the capacity to produce rapid antidepressant effects. However, unlike ketamine, norketamine, and HNK, DHNK has been found to be inactive in the forced swim test (FST) in mice at doses up to 50 mg/kg. DHNK is inactive at the α3β4-nicotinic acetylcholine receptor (IC50 > 100 μM) and is only very weakly active at the NMDA receptor (Ki = 38.95 μM for (S)-(+)-DHNK). It can be detected 7–10 days after a modest dose of ketamine, and because of this, is useful in drug detection assays.

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