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Description: Selective AMPA agonist; active isomer of (RS)-AMPA (Cat. No. 0169)
Chemical Name: (S)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
Purity: ≥99% (HPLC)
Biological Activity for (S)-AMPA
(S)-AMPA is an active enantiomer of AMPA (EC50 = 3.5 μM).
NPEC-caged-(S)-AMPA, Inactive Enantiomer and Racemate also available.
Technical Data for (S)-AMPA
| M. Wt | 186.17 |
| Formula | C7H10N2O4 |
| Storage | Store at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 83643-88-3 |
| PubChem ID | 158397 |
| InChI Key | UUDAMDVQRQNNHZ-YFKPBYRVSA-N |
| Smiles | [H][C@@](N)(C(O)=O)CC1=C(C)ON=C1O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for (S)-AMPA
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| water | 9.31 | 50 |
Preparing Stock Solutions for (S)-AMPA
The following data is based on the product molecular weight 186.17. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.5 mM | 10.74 mL | 53.71 mL | 107.43 mL |
| 2.5 mM | 2.15 mL | 10.74 mL | 21.49 mL |
| 5 mM | 1.07 mL | 5.37 mL | 10.74 mL |
| 25 mM | 0.21 mL | 1.07 mL | 2.15 mL |
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Product Datasheets for (S)-AMPA
References for (S)-AMPA
References are publications that support the biological activity of the product.
Falch et al (1998) Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure-activity relationships. J.Med.Chem. 41 2513 PMID: 9651156
Hansen et al (1983) Enzymic resolution and binding to rat brain membranes of the glutamic acid agonist α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid. J.Med.Chem. 26 901 PMID: 6133955
Lauridsen et al (1985) Ibotenic acid analogues. Synthesis, molecular flexibility, and in vitro activity of agonists and antagonists at central glutamic acid receptors. J.Med.Chem. 28 668 PMID: 2859375
If you know of a relevant reference for (S)-AMPA, please let us know.
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Keywords: (S)-AMPA, (S)-AMPA supplier, Selective, AMPA, agonists, Glutamate, Receptors, iGluR, Ionotropic, 0254, Tocris Bioscience
13 Citations for (S)-AMPA
Citations are publications that use Tocris products. Selected citations for (S)-AMPA include:
Temkin et al (2017) The Retromer Supports AMPA Receptor Trafficking During LTP. Neuron 94 74 PMID: 28384478
Wagner et al (2019) Myosin VI Drives Clathrin-Mediated AMPA Receptor Endocytosis to Facilitate Cerebellar Long-Term Depression. Cell Rep 28 11 PMID: 31269433
Langner et al (2017) Kynurenic Acid Induces Impairment of Oligodendrocyte Viability: On the Role of Glutamatergic Mechanisms. Neurochem Res 42 838 PMID: 27444613
Bell et al (2015) Neuronal development is promoted by weakened intrinsic antioxidant defences due to epigenetic repression of Nrf2. PLoS One 6 7066 PMID: 25967870
Fairless et al (2013) Membrane potential measurements of isolated neurons using a voltage-sensitive dye. PLoS One 8 e58260 PMID: 23516458
Park et al (2016) Involvement of AMPA Receptor and Its Flip and Flop Isoforms in Retinal Ganglion Cell Death Following Oxygen/Glucose Deprivation. Invest Ophthalmol Vis Sci 57 508 PMID: 26868754
Jackson et al (2010) Control of cerebellar long-term potentiation by P-Rex-family guanine-nucleotide exchange factors and phosphoinositide 3-kinase. PLoS One 5 e11962 PMID: 20694145
Oh et al (2012) Overexpression of calcium-permeable glutamate receptors in glioblastoma derived brain tumor initiating cells. EMBO Rep 7 e47846 PMID: 23110111
Lussier et al (2011) Activity-dependent ubiquitination of the AMPA receptor subunit GluA2. Proc Natl Acad Sci U S A 31 3077 PMID: 21414928
Pooler et al (2013) Physiological release of endogenous tau is stimulated by neuronal activity. J Neurosci 14 389 PMID: 23412472
Limon et al (2007) Properties of GluR3 receptors tagged with GFP at the amino or carboxyl terminus. Neuroreport 104 15526 PMID: 17881566
Underhill (2007) Hypoxic injury of isolated axons is independent of ionotropic glutamate receptors. Neurobiol Dis 25 284 PMID: 17071096
Gasull-Camôs Serotonergic mechanisms involved in antidepressant-like responses evoked by GLT-1 blockade in rat infralimbic cortex. Neuropharmacology 139 41 PMID: 29940206
Do you know of a great paper that uses (S)-AMPA from Tocris? Please let us know.
Reviews for (S)-AMPA
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Test of AMPA effect on VGCCs-generated transmembrane current.
By
Sergiy Sylantyev on 12/10/2023
Assay Type: In Vitro
Species: Mouse
Cell Line/Tissue: Arcuate nucleus
10 μM AMPA was used to clarify the input of AMPA receptors into 5HT-1B receptors - activated modulation of voltage-gated calcium channel gating. Left: control. Right: the effect of activation of 5HT-1B and AMPA receptors on transmembrane current through VGCCs evoked upon membrane depolarization. Blue trace: control; red trace: 5HT-1B and AMPA receptors activation.
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