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SML1875

Sigma-Aldrich

(2S,6S)-Hydroxynorketamine hydrochloride

≥98% (HPLC)

Synonym(s):

(2S,6S)-2-Amino-2-(2-chlorophenyl)-6-hydroxy-cyclohexanone hydrochloride, (2S,6S)-HNK hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C12H14ClNO2 · HCl
CAS Number:
Molecular Weight:
276.16
UNSPSC Code:
12352116
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +95 to +115°, c = 1 in H2O

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

desiccated

color

white to beige

solubility

H2O: 25 mg/mL, clear

storage temp.

2-8°C

SMILES string

[H]Cl.ClC1=CC=CC=C1[C@](CCC[C@@H]2O)(N)C2=O

Related Categories

Biochem/physiol Actions

(2S,6S)-Hydroxynorketamine hydrochlorideKetamine is a metabolite associated with increased locomotor activity and motor incoordination.
It has been found that the NMDAR antagonist (R,S)-ketamine must be metabolized to (2S,6S;2R,6R)-hydroxynorketamine (HNK) to have antidepressant effects. The (2R,6R)-HNK enantiomer appears to be the enantiomer most responsible for antidepressant effects, while (2S,6S)-hydroxynorketamine was associated with increased locomotor activity and motor incoordination. (2S,6S)-HNK, was also found to increase the function of the mammalian target of rapamycin (mTOR) 2-fold at 0.05 nM. (2S,6S)-HNK and (2R,6R)-HNK both inhibited intracellular concentrations of D-serine, an endogenous NMDA receptor co-agonist, with IC50 values of 0.18 nM and 0.68 nM, respectively. Neither bind with high affinity to NMDA receptors, with Ki values of 21.19 μM and > 100 μM for (2S,6S)-HNK and (2R,6R)-HNK, respectively.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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Nagendra S Singh et al.
PloS one, 11(4), e0149499-e0149499 (2016-04-21)
D-Serine is an endogenous NMDA receptor co-agonist that activates synaptic NMDA receptors modulating neuronal networks in the cerebral cortex and plays a key role in long-term potentiation of synaptic transmission. D-serine is associated with NMDA receptor neurotoxicity and neurodegeneration and
Panos Zanos et al.
Nature, 533(7604), 481-486 (2016-05-05)
Major depressive disorder affects around 16 per cent of the world population at some point in their lives. Despite the availability of numerous monoaminergic-based antidepressants, most patients require several weeks, if not months, to respond to these treatments, and many
Rajib K Paul et al.
Anesthesiology, 121(1), 149-159 (2014-06-18)
Subanesthetic doses of (R,S)-ketamine are used in the treatment of neuropathic pain and depression. In the rat, the antidepressant effects of (R,S)-ketamine are associated with increased activity and function of mammalian target of rapamycin (mTOR); however, (R,S)-ketamine is extensively metabolized

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