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SML1873 Sigma-Aldrich

(2R,6R)-Hydroxynorketamine hydrochloride

≥98% (HPLC)

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

  • CAS Number 1430202-69-9

  • Empirical Formula (Hill Notation) C12H14ClNO2 · HCl

  • Molecular Weight 276.16

  •  MDL number MFCD30182371

  •  NACRES NA.77

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Properties

Related Categories 0-9, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
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
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

Packaging

5, 25 mg in glass bottle

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 & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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