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SML1873

(2R,6R)-Hydroxynorketamine hydrochloride

≥98% (HPLC), AMPA receptors agonist, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H14ClNO2 · HCl
CAS Number:
1430202-69-9
Molecular Weight:
276.16
UNSPSC Code:
12352116
NACRES:
NA.77
MDL number:
MFCD30182371
Assay:
≥98% (HPLC)
Form:
powder
Storage condition:
desiccated
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Product Name

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

Quality Segment

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

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

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-;/m1./s1

InChI key

ZQJVHBJDLMIKJK-MHDYBILJSA-N

Biochem/physiol Actions

(2R,6R)-Hydroxynorketamine is a ketamine metabolite that has rapid antidepressant activity without ketamine-related side effects.
(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
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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