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SML1873

(2R,6R)-Hydroxynorketamine hydrochloride

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

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

Synonym(e):

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

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Über diesen Artikel

Empirische Formel (Hill-System):

C₁₂H₁₄ClNO₂· HCl

CAS-Nummer:

1430202-69-9

Molekulargewicht:

276.16

UNSPSC Code:

12352116

NACRES:

NA.77

MDL number:

MFCD30182371

Assay:

≥98% (HPLC)

Form:

powder

Storage condition:

desiccated

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Eigenschaften

Produktname

(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

Beschreibung

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.