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SML1873

Sigma-Aldrich

(2R,6R)-Hydroxynorketamine hydrochloride

≥98% (HPLC)

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Synonym(s):
(2R,6R)-HNK hydrochloride; (2R,6R)-2-Amino-2-(2-chlorophenyl)-6-hydroxy-cyclohexanone hydrochloride
Empirical Formula (Hill Notation):
C12H14ClNO2 · HCl
CAS Number:
Molecular Weight:
276.16
MDL number:
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

O=C1[C@@](C2=CC=CC=C2Cl)(N)CCC[C@H]1O.Cl

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This Item
K2753SML1875SML0362
(±)-Ketamine hydrochloride solid

K2753

(±)-Ketamine hydrochloride

NPS2143 hydrochloride ≥98% (HPLC)

SML0362

NPS2143 hydrochloride

form

powder

form

solid

form

powder

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

drug control

-

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

drug control

-

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

H2O: 25 mg/mL, clear

solubility

-

solubility

H2O: 25 mg/mL, clear

solubility

DMSO: >10 mg/mL

Biochem/physiol Actions

(2R,6R)-Hydroxynorketamine is a ketamine metabolite that has rapid antidepressant activity without ketamine-related side effects. 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 in a mouse study and unlike (2S,6S)-HNK, (2R,6R)-HNK caused no significant changes in locomotion or coordination. (2R,6R)-HNK does not seem to have the same addiction potential as ketamine, since mice did not self-administer pharmacologically relevant doses of (2R,6R)-HNK under the same conditions where ketamine was readily self-administered. The (2R,6R)-HNK antidepressant appears to involve activation of AMPA glutamate receptors rather than inhibition of NMDA glutamate receptors.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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

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