Hydroxynorketamine

Structural formula
Structural formula without stereochemistry
General
Surname	Hydroxynorketamine
other names	2-Amino-2- (2-chlorophenyl) -6-hydroxycyclohexanone ( IUPAC )
Molecular formula	C 12 H 14 ClNO 2
External identifiers / databases
CAS number 81395-70-2 PubChem 133669 ChemSpider 117907 Wikidata Q20164362
Drug information
Drug class	antidepressant
properties
Molar mass	239.70 g · mol -1
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hydroxynorketamine ( HNK ) is a metabolite of ketamine , which is formed by hydroxylation of its metabolite norketamine. In contrast to ketamine and norketamine, hydroxynorketamine is inactive as an anesthetic and dissociative and does not produce intoxication .

Stereochemistry

Hydroxynorketamine has two chiral centers , so there are four stereoisomers .

Stereoisomers of hydroxynorketamine
(2 R , 6 R ) stereoisomer	(2 S , 6 S ) stereoisomer	(2 R , 6 S ) stereoisomer	(2 S , 6 R ) stereoisomer

pharmacology

The pharmacological effect of ketamine in depression is attributed to the metabolite (2 R , 6 R ) -hydroxynorketamine. This was first demonstrated in 2016 and published in the journal Nature . (2 R , 6 R ) -HNK showed antidepressant-like effects even 3 days after administration to mice. In contrast to ketamine, HNK hardly has any effect on the NMDA receptors (K _i = 21.19 µM for (2 S , 6 S ) -HNK and> 100 µM for (2 R , 6 R ) -HNK), but rather mediates its effect via AMPA receptors . HNK has no addictive effect in mice.

Web links

• Govi-Verlag Pharmazeutischer Verlag: Ketamine: Metabolit has a rapid antidepressant effect. In: pharmische-zeitung.de. May 6, 2016, Retrieved May 8, 2016 . 
• Ketamine lifts depression via a byproduct of its metabolism. In: nih.gov. May 4, 2016, accessed May 7, 2016 . 

Individual evidence

1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
2. ↑ Ronald D. Miller, Lars I. Eriksson, Lee A Fleisher, Jeanine P. Wiener-Kronish, William L. Young: Anesthesia . Elsevier Health Sciences, June 24, 2009, ISBN 1-4377-2061-7 , pp. 743-.
3. ↑ Louis Y. Leung, Thomas A. Baillie: Comparative pharmacology in the rat of ketamine and its two principal metabolites, norketamine and (Z) -6-hydroxynorketamine. In: Journal of Medicinal Chemistry. 29, 1986, p. 2396, doi : 10.1021 / jm00161a043 .
4. ↑ Irving W. Wainer: Are basal D-serine plasma levels a predictive biomarker for the rapid antidepressant effects of ketamineand ketamine metabolites ?. In: Psychopharmacology. 231, 2014, p. 4083, doi : 10.1007 / s00213-014-3736-6 .
5. ↑ ^{a b c} Panos Zanos, Ruin Moaddel u. a .: NMDAR inhibition-independent antidepressant actions of ketamine metabolites. In: Nature. 2016, doi : 10.1038 / nature17998 .
6. ↑ ruin Moaddel, Galia Abdrakhmanova u. a .: Sub-anesthetic concentrations of (R, S) -ketamine metabolites inhibit acetylcholine-evoked currents in α7 nicotinic acetylcholine receptors. In: European Journal of Pharmacology. 698, 2013, p. 228, doi : 10.1016 / j.ejphar.2012.11.023 .
7. ↑ Nagendra S Singh, Carlos A Zarate, Ruin Moaddel, Michel Bernier, Irving W Wainer: What is hydroxynorketamine and what can it bring to neurotherapeutics? In: Expert Review of Neurotherapeutics. 14, 2014, p. 1239, doi : 10.1586 / 14737175.2014.971760 .

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