SML1873

(2R,6R)-Hydroxynorketamine hydrochloride

≥98% (HPLC)

• 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: 1430202-69-9
• Molecular Weight: 276.16
• MDL number: MFCD30182371
• UNSPSC Code: 12352116
• NACRES: NA.77

Properties

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

Description

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302,H315,H319
• pcodes: P264 - P270 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• 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