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
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About This Item
Empirical Formula (Hill Notation):
C12H14ClNO2 · HCl
CAS Number:
Molecular Weight:
276.16
UNSPSC Code:
12352116
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Storage condition:
desiccated
Product Name
(2S,6S)-Hydroxynorketamine hydrochloride, ≥98% (HPLC)
Quality Segment
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
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.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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