Key Documents

View All Documentation

SML1875

(2S,6S)-Hydroxynorketamine hydrochloride

Name: (2S,6S)-Hydroxynorketamine hydrochloride
Brand: SIGMA

≥98% (HPLC), Ketamine metabolite, powder

Synonym(s):

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

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₄ClNO₂ · HCl

CAS Number:

1430202-70-2

Molecular Weight:

276.16

UNSPSC Code:

12352116

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Product Name

(2S,6S)-Hydroxynorketamine hydrochloride, ≥98% (HPLC)

Quality Level

100

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

InChI

1S/C12H14ClNO2.ClH/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;1H/t10-,12-;/m0./s1

InChI key

ZQJVHBJDLMIKJK-JGAZGGJJSA-N

Related Categories

Bioactive Small Molecules

Biochem/physiol Actions

(2S,6S)-Hydroxynorketamine hydrochlorideKetamine is a metabolite associated with increased locomotor activity and motor incoordination.

(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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

0000382397

0000216976

0000143425

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

NMDAR inhibition-independent antidepressant actions of ketamine metabolites.

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

Ketamine Metabolites Enantioselectively Decrease Intracellular D-Serine Concentrations in PC-12 Cells.

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

(R,S)-Ketamine metabolites (R,S)-norketamine and (2S,6S)-hydroxynorketamine increase the mammalian target of rapamycin function.

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

Global Trade Item Number

SKU	GTIN
SML1875-5MG	04061833265468
SML1875-25MG	04061833265451

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service