Structure via PubChem · Public domain (PubChem)
hydroxynorketamine
Sign in to saveAlso known as 6-hydroxynorketamine
Hydroxynorketamine (HNK), or 6-hydroxynorketamine, is a minor metabolite of the anesthetic, dissociative, and antidepressant drug ketamine. It is formed by hydroxylation of the intermediate norketamine, another metabolite of ketamine. As of late 2019, '(2R,6R)-HNK' is in clinical trials for the treatment of depression.
Chemical data
- Formula
- C12H14ClNO2
- Molecular weight
- 239.7 g/mol
- IUPAC name
- 2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one
- SMILES
- C1CC(C(=O)C(C1)(C2=CC=CC=C2Cl)N)O
- InChIKey
- CFBVGSWSOJBYGC-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 63.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 239.071306
Show 3 more facts
- Commons category
- Hydroxynorketamine
- chemical formula
- C₁₂H₁₄ClNO₂
- canonical SMILES
- C1CC(C(=O)C(C1)(C2=CC=CC=C2Cl)N)O
Sources (2)
via Wikidata · CC0
~6 min read
Encyclopedic overview
4 sectionsContents
- Pharmacology
- Research
- See also
- References
Hydroxynorketamine (HNK), or 6-hydroxynorketamine, is a minor metabolite of the anesthetic, dissociative, and antidepressant drug ketamine. It is formed by hydroxylation of the intermediate norketamine, another metabolite of ketamine. As of late 2019, '(2R,6R)-HNK' is in clinical trials for the treatment of depression.
The major metabolite of ketamine is norketamine (80%). Norketamine is secondarily converted into 4-, 5-, and 6-hydroxynorketamines (15%), mainly HNK (6-hydroxynorketamine). Ketamine is also transformed into hydroxyketamine (5%). As such, bioactivated HNK comprises less than 15% of a dose of ketamine.
Excerpted from Wikipedia’s “hydroxynorketamine” article, available under the CC BY-SA 4.0 licence.