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SML1875

Sigma-Aldrich

(2S,6S)-Hydroxynorketamine hydrochloride

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C12H14ClNO2 · HCl
Numéro CAS:
Poids moléculaire :
276.16
Code UNSPSC :
12352116

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Activité optique

[α]/D +95 to +115°, c = 1 in H2O

Contrôle du médicament

regulated under CDSA - not available from Sigma-Aldrich Canada

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

H2O: 25 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

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

Actions biochimiques/physiologiques

(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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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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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