Hydroxynorketamine

Hydroxynorketamine
(2R,6R)-Hydroxynorketamine
(2S,6S)-Hydroxynorketamine
The four possible stereoisomers of Hydroxynorketamine
(2R,6S)-Hydroxynorketamine (2S,6R)-Hydroxynorketamine
Clinical data
Other namesHNK; 6-Hydroxynorketamine; 6-HNK
ATC code
  • None
Identifiers
  • 2-Amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H14ClNO2
Molar mass239.70 g·mol−1
3D model (JSmol)
  • C1CC(C(=O)C(C1)(C2=CC=CC=C2Cl)N)O
  • InChI=1S/C12H14ClNO2/c13-9-5-2-1-4-8(9)12(14)7-3-6-10(15)11(12)16/h1-2,4-5,10,15H,3,6-7,14H2
  • Key:CFBVGSWSOJBYGC-UHFFFAOYSA-N

Hydroxynorketamine (HNK), or 6-hydroxynorketamine, is a minor metabolite of the anesthetic, dissociative, and antidepressant drug ketamine.[1] It is formed by hydroxylation of the intermediate norketamine, another metabolite of ketamine.[1] As of late 2019, (2R,6R)-HNK is in clinical trials for the treatment of depression.[2]

The major metabolite of ketamine is norketamine (80%).[3] Norketamine is secondarily converted into 4-, 5-, and 6-hydroxynorketamines (15%), mainly HNK (6-hydroxynorketamine).[3] Ketamine is also transformed into hydroxyketamine (5%).[3] As such, bioactivated HNK comprises less than 15% of a dose of ketamine.[3]

  1. ^ a b Miller RD, Eriksson LI, Fleisher LA, Wiener-Kronish JP, Young WL (24 June 2009). Anesthesia. Elsevier Health Sciences. pp. 743–. ISBN 978-1-4377-2061-7.
  2. ^ Cite error: The named reference Hashimoto2019 was invoked but never defined (see the help page).
  3. ^ a b c d Mion G, Villevieille T (June 2013). "Ketamine pharmacology: an update (pharmacodynamics and molecular aspects, recent findings)". CNS Neuroscience & Therapeutics. 19 (6): 370–380. doi:10.1111/cns.12099. PMC 6493357. PMID 23575437.