Dehydronorketamine

Dehydronorketamine

Systematic (IUPAC) name
6-Amino-6-(2-chlorophenyl)cyclohex-2-en-1-one
Identifiers
CAS Number	57683-62-2
ATC code	None
PubChem	CID: 162835
ChemSpider	142954
Chemical data
Formula	C12H12ClNO
Molecular mass	221.68278 g/mol
SMILES C1CC(C(=O)C=C1)(C2=CC=CC=C2Cl)N
InChI 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 (K_i = 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.

See also

• Arketamine
• Esketamine