SML1875

(2S,6S)-Hydroxynorketamine hydrochloride

≥98% (HPLC), Ketamine metabolite, powder

• Synonym(s): (2S,6S)-2-Amino-2-(2-chlorophenyl)-6-hydroxy-cyclohexanone hydrochloride, (2S,6S)-HNK hydrochloride
• 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
• Storage condition: desiccated

Properties

• Product Name: (2S,6S)-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: [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

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable