(S)-AMPA - CAS 83643-88-3
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C7H10N2O4
Molecular Weight:
186.17
COA:
Inquire
Targets:
AMPAR
Description:
(S)-AMPA is an active enantiomer of AMPA, which has been found to be a definitive agonist of the AMPA glutamatergic ionotropic receptor.
Purity:
≥99% by HPLC
Appearance:
White Solid
Synonyms:
(S)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
MSDS:
Inquire
InChIKey:
UUDAMDVQRQNNHZ-YFKPBYRVSA-N
InChI:
InChI=1S/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1
Canonical SMILES:
CC1=C(C(=O)NO1)CC(C(=O)O)N
1.5-(N-oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: novel, systemically active and broad spectrum antagonists for NMDA/glycine, AMPA, and kainate receptors.
Cai SX;Huang JC;Espitia SA;Tran M;Ilyin VI;Hawkinson JE;Woodward RM;Weber E;Keana JF J Med Chem. 1997 Oct 24;40(22):3679-86.
A group of 5-aza-7-substituted-1,4-dihydroquinoxaline-2,3-diones (QXs) and the corresponding 5-(N-oxyaza)-7-substituted QXs were prepared and evaluated as antagonists of ionotropic glutamate receptors. The in vitro potency of these QXs was determined by inhibition of [3H]-5,7-dichlorokynurenic acid ([3H]DCKA) binding to N-methyl-D-aspartate (NMDA)/glycine receptors, [3H]-(S)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid ([3H]AMPA) binding to AMPA receptors, and [3H]kainate ([3H]KA) binding to KA receptors in rat brain membranes. 5-(N-Oxyaza)-QXs 12a-e all have low micromolar or submicromolar potency for NMDA/glycine receptors and low micromolar potencies for AMPA and KA receptors. QXs 12a-e display 2-12-fold selectivity for NMDA/glycine receptors compared to AMPA receptors, and approximately 2-fold difference between AMPA and KA potency. In contrast to other QXs that either show high selectivity for NMDA (such as ACEA 1021) or AMPA (such as NBQX) receptors, these molecules are broad spectrum antagonists of ionotropic glutamate receptors. 7-Nitro-5-(N-oxyaza)-QX (12e) is the most potent inhibitor among 12a-e, having IC50 values of 0.69, 1.3, and 2.4 microM at NMDA, AMPA, and KA receptors, respectively.
2.The effects of AMPA receptor antagonists in models of stroke and neurodegeneration.
Gressens P;Spedding M;Gigler G;Kertesz S;Villa P;Medja F;Williamson T;Kapus G;Levay G;Szenasi G;Barkoczy J;Harsing LG Jr Eur J Pharmacol. 2005 Sep 5;519(1-2):58-67.
Alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonists have been shown to have neuroprotective effects in stroke models and although clinical trials with some agents are still ongoing, published results have not been favourable. We therefore wished to compare the effects of GYKI 52466, GYKI 53405, EGIS-8332 and EGIS-10608, non-competitive AMPA receptor antagonists with homophthalazine chemical structures, in standard animal stroke models with effects in a neurodegenerative model--excitoxicity in newborn mice. All compounds inhibited the S-AMPA-induced spreading depression in the chicken retina, in vitro, and were potent anticonvulsants against maximal electroshock in mice, in vivo. The AMPA receptor antagonists prevented domoate-induced cell death of motoneurons, in vitro, and reduced infarct size in a dose-dependent manner in the permanent middle cerebral artery occlusion model in mice, in vivo. In newborn mice (P5, histopathology at P10), local injection of the AMPA receptor agonist S-bromo-willardiine at day 5 after birth induced cortical damage and white matter damage, which was reduced in a dose-dependent manner by the AMPA receptor antagonists. EGIS 10608 was a very powerful receptor antagonist of white matter damage.
3.(S)-2,3-dihydro-[3,4]cyclopentano-1,2,4-benzothiadiazine-1,1-dioxide: (S18986-1) a positive modulator of AMPA receptors enhances (S)-AMPA-mediated [3H]noradrenaline release from rat hippocampal and frontal cortex slices.
Lockhart B;Iop F;Closier M;Lestage P Eur J Pharmacol. 2000 Aug 4;401(2):145-53.
The present study describes the effect of (S)-2,3-dihydro-[3, 4]cyclopentano-1,2,4-benzothiadiazine-1,1-dioxide (S18986-1), a positive allosteric modulator of the alpha-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptors with cognitive-enhancing effects, on (S)-AMPA-induced [3H]noradrenaline release in rat hippocampal and frontal cortex slices. (S)-AMPA significantly increased [3H]noradrenaline release in rat hippocampus and frontal cortex slices, whereas S18986-1 (3-1000 microM) alone, was inactive. However, S18986-1 between 30 and 1000 microM potently enhanced (+200%) (S)-AMPA-mediated [3H]noradrenaline release in both hippocampal and frontal cortex slices. The capacity of S18986-1 to potentiate [3H]noradrenaline release was specific for AMPA receptors as S18986-1 failed to potentiate either kainate and N-methyl-D-aspartate (NMDA)-mediated release of [3H]noradrenaline in rat hippocampal slices. Moreover, 1, 2,3,4-tetrahydro-6-nitro-2,3-dioxo-benzo[f]quinoxaline-7-sulfonamide (NBQX) and 1-(4-aminophenyl)-3-methylcarbamoyl-4-methyl-3, 4-dihydro-7,8-methylenedioxy-5H-2,3-benzodiazepine (GYKI-53655) but not (5R,10S)-(+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5, 10-imine ((+)-MK-801), inhibited (S)-AMPA and S18986-induced stimulation of (S)-AMPA-mediated [3H]noradrenaline release.
Molecular Weight Calculator Molarity Calculator Solution Dilution Calculator

Related AMPAR Products


EGIS-8332
(CAS: 220725-87-1)

EGIS-8332 potently decreased AMPA and quisqualate induced LDH release (IC50 = 5.2 ± 0.4 and 7.4 ± 1.3 μM, respectively) from the cells. The inhibition of the AM...

CAS 143692-18-6 GYKI 53655

GYKI 53655
(CAS: 143692-18-6)

GYKI 53655 is a selective AMPA receptor antagonist with anticonvulsant activity.

CAS 2259-96-3 Cyclothiazide

Cyclothiazide
(CAS: 2259-96-3)

Cyclothiazide has been found to be a subunit-specific inhibitor of GABAC receptors and could be used as a diuretic agent as well as antihypertensive agent.

CAS 1026791-61-6 Org-26576

Org-26576
(CAS: 1026791-61-6)

Org-26576 is a positive allosteric modulator of AMPA receptor. Org-26576 increases the anteroventral and laterodorsal thalamus, cingulate cortex, dentate gyrus ...

CAS 211735-76-1 Farampator

Farampator
(CAS: 211735-76-1)

Farampator, also called as CX-691 or Org24448, is an AMPA receptor positive allosteric modulator and glycine reuptake inhibitor potentially for the treatment of...

CAS 201730-10-1 (R)-3,4-DCPG

(R)-3,4-DCPG
(CAS: 201730-10-1)

(R)-3,4-DCPG is an AMPA receptor antagonist with weak activity at NMDA receptors and no activity at kainate receptors.

CAS 375345-95-2 LY451395

LY451395
(CAS: 375345-95-2)

Incubation of LY451395 with Actinoplanes missouriensis NRRL B3342 generated several metabolites that were previously detected in the in vivo metabolism studies ...

LY-326325
(CAS: 177314-99-7)

LY-326325, a decahydroisoquinaline derivative, has been found to be an AMPA receptor antagonist and was once studied for neuroprotection.

Chemical Structure

CAS 83643-88-3 (S)-AMPA

Quick Inquiry

Verification code

Featured Items