(S)-a-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acidAn active isomer of AMPA with no NMDAR activity

(S)-a-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (CAS 83643-88-3)

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Synonym: (S)-AMPA; AMQ; glutamate-AMPA
Application: An active isomer of AMPA with no NMDAR activity
CAS Number: 83643-88-3
Molecular Weight: 186.17
Molecular Formula: C7H10N2O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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(S)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid is an active enantiomer of AMPA ((R,S)-AMPA) that induces apoptotic cell death in cortical neurons. Does not exhibit any affinity for NMDA receptors. (S)-a-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid is an activator of GluR.


References

John, C.A., et al. 1999. Neurosci. Lett. 268, 9. Bang-Andersen, B., et al. 1997. J. Med. Chem. 40, 2831. Lauridsen, J., et al. 1985. J. Med. Chem. 28, 668. Hansen, J.J., et al. 1983. J. Med. Chem. 26, 901.

Physical State :
Solid
Solubility :
Soluble in water (100 mM), 1 M HCl (50 mg/ml), and dilute aqueous base.
Storage :
Store at 4° C
Melting Point :
297.85° C (Predicted)
Boiling Point :
~425.6° C at 760 mmHg (Predicted)
Density :
~1.5 g/cm3 (Predicted)
Refractive Index :
n20D 1.54 (Predicted)
Optical Activity :
α20/D -19.8°, c = 1 in water
IC50 :
Glutamate receptor ionotropic, AMPA: IC50 = 6.2 nM (rat); Rat: IC50 = 0.6 µM; Glutamate receptor ionotropic, kainate: IC50 = 24 µM (rat); Glutamate NMDA receptor: IC50 >100 µM (rat); Glutamate [NMDA] receptor subunit epsilon 3: IC50 >100 µM (rat)
Ki Data :
GluR-2: Ki= 16.8 nM (human); GluR-3: Ki= 20.6 nM (human); Glutamate receptor ionotropic, AMPA 3: Ki= 21 nM (rat); GluR-1: Ki= 21.9 nM (human); Glutamate receptor ionotropic, AMPA 1: Ki= 22 nM (rat)
pK Values :
pKa: 1.99 (Predicted), pKb: 9.01 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
158397
Merck Index :
14: 578
MDL Number :
MFCD00672630
SMILES :
CC1=C(C(=O)NO1)C[C@@H](C(=O)O)N

Download SDS (MSDS)

Certificate of Analysis

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