Dehydronorketamine

Dehydronorketamine
Clinical data
ATC code	None;
Identifiers
	IUPAC name 6-Amino-6-(2-chlorophenyl)cyclohex-2-en-1-one;
CAS Number	57683-62-2;
PubChem CID	162835;
ChemSpider	142954;
UNII	J5442FVV58;
CompTox Dashboard (EPA)	DTXSID80973283 ;
Chemical and physical data
Formula	C12H12ClNO
Molar mass	221.68 g·mol−1
3D model (JSmol)	Interactive image;
	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.^[1]^[2] Though originally considered to be inactive,^[1]^[2]^[3] DHNK has been found to act as a potent and selective negative allosteric modulator of the α₇-nicotinic acetylcholine receptor (IC₅₀ = 55 nM).^[4]^[5] For this reason, similarly to hydroxynorketamine (HNK), it has been hypothesized that DHNK may have the capacity to produce rapid antidepressant effects.^[6] 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.^[7] 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).^[4] It can be detected 7–10 days after a modest dose of ketamine, and because of this, is useful in drug detection assays.^[8]