(S)-AMPA

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Cat.No. 0254 - (S)-AMPA | C7H10N2O4 | CAS No. 83643-88-3
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)
Datasheet
Citations (10)
Reviews
Literature

Biological Activity

Active enantiomer of AMPA (EC50 = 3.5 μM).

Available as part of the AMPA Receptor Tocriset™. NPEC-caged-(S)-AMPA, Inactive Enantiomer and Racemate also available.

Technical Data

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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
water 18.62 100

Preparing Stock Solutions

The following data is based on the product molecular weight 186.17. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 5.37 mL 26.86 mL 53.71 mL
5 mM 1.07 mL 5.37 mL 10.74 mL
10 mM 0.54 mL 2.69 mL 5.37 mL
50 mM 0.11 mL 0.54 mL 1.07 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

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


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Keywords: (S)-AMPA, (S)-AMPA supplier, Selective, AMPA, agonists, Glutamate, Receptors, iGluR, Ionotropic, 0254, Tocris Bioscience

10 Citations for (S)-AMPA

Citations are publications that use Tocris products. Selected citations for (S)-AMPA include:

Langner et al (2017) Kynurenic Acid Induces Impairment of Oligodendrocyte Viability: On the Role of Glutamatergic Mechanisms. Neurochem Res 42 838 PMID: 27444613

Pooler et al (2013) Physiological release of endogenous tau is stimulated by neuronal activity. J Neurosci 14 389 PMID: 23412472

Oh et al (2012) Overexpression of calcium-permeable glutamate receptors in glioblastoma derived brain tumor initiating cells. EMBO Rep 7 e47846 PMID: 23110111

Underhill (2007) Hypoxic injury of isolated axons is independent of ionotropic glutamate receptors. Neurobiol Dis 25 284 PMID: 17071096

Lussier et al (2011) Activity-dependent ubiquitination of the AMPA receptor subunit GluA2. Proc Natl Acad Sci U S A 31 3077 PMID: 21414928

Limon et al (2007) Properties of GluR3 receptors tagged with GFP at the amino or carboxyl terminus. Neuroreport 104 15526 PMID: 17881566

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

Fairless et al (2013) Membrane potential measurements of isolated neurons using a voltage-sensitive dye. PLoS One 8 e58260 PMID: 23516458

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


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Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* or download your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.


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