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A6816

Sigma-Aldrich

(±)-AMPA

solid

Synonym(s):

(±)-α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid hydrate

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1 MG
$160.00
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$464.58
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$856.00

$160.00

Estimated to ship onApril 14, 2025

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1 MG
$160.00
5 MG
$464.58
10 MG
$856.00

About This Item

Empirical Formula (Hill Notation):
C7H10N2O4
Molecular Weight:
186.17
MDL number:
MFCD00213388
UNSPSC Code:
12352100
PubChem Substance ID:
24891141
NACRES:
NA.32

$160.00

Estimated to ship onApril 14, 2025

form

solid

color

white

solubility

H2O: 1 mg/mL (warm)
0.1 M HCl: 3.5 mg/mL
0.1 M NaOH: 4.3 mg/mL
DMSO: 4.3 mg/mL
1 M HCl: 50 mg/mL

SMILES string

O.Cc1onc(O)c1CC(N)C(O)=O

InChI

1S/C7H10N2O4.H2O/c1-3-4(6(10)9-13-3)2-5(8)7(11)12;/h5H,2,8H2,1H3,(H,9,10)(H,11,12);1H2

InChI key

HFISYNCCKQHIAM-UHFFFAOYSA-N

Gene Information

rat ... Gria1(50592) , Gria2(29627) , Gria3(29628) , Gria4(29629) , Grik1(29559) , Grik2(54257) , Grin2a(24409) , Grm1(24414) , Grm2(24415) , Grm4(24417) , Grm5(24418) , Slc1a1(25550) , Slc1a2(29482) , Slc1a3(29483)

Application

(±)-AMPA has been used:
  • in vivo

  • whole-cell patch-clamp recording in Müller glial cells[1]
  • to test its excitotoxic effects in hippocampal slice cultures[2]
  • in retinal horizontal cells (HCs) culture to test its effect on Ca2+ signals[3]

Biochem/physiol Actions

Potent excitatory amino acid that interacts selectively with central AMPA/kainate receptors.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
049K37921V
049K37921
049K3792
037K3797
074H38523

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Carlos Gonzalez-Islas et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(39), 13597-13607 (2012-09-28)
Endocannabinoid signaling has been shown to mediate synaptic plasticity by retrogradely inhibiting presynaptic transmitter release in several systems. We found that endocannabinoids act tonically to regulate AMPA miniature postsynaptic current (mPSC) frequency in embryonic motor circuits of the chick spinal
B W Kristensen et al.
Brain research, 917(1), 21-44 (2001-10-17)
The excitotoxic profiles of (RS)-2-amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propionic acid (ATPA), (RS)-2-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA), kainic acid (KA) and N-methyl-D-aspartate (NMDA) were evaluated using cellular uptake of propidium iodide (PI) as a measure for induced, concentration-dependent neuronal damage in hippocampal slice cultures. ATPA is
Joonwoo Lee et al.
Biological & pharmaceutical bulletin, 36(3), 331-338 (2013-03-02)
Various effects of acorn extract have been reported including antioxidant activity, cytotoxicity against cancer cells, and the levels of acetylcholine and its related enzyme activities in the dementia mouse models. However, it is unclear whether acorn extract inhibits glutamate-induced calcium
Camille A Chapot et al.
Current biology : CB, 27(23), 3603-3615 (2017-11-28)
The mouse retina contains a single type of horizontal cell, a GABAergic interneuron that samples from all cone photoreceptors within reach and modulates their glutamatergic output via parallel feedback mechanisms. Because horizontal cells form an electrically coupled network, they have
Stuti J Jaiswal et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(6), 2616-2625 (2013-02-09)
Developmental nicotine exposure (DNE) impacts central respiratory control in neonates born to smoking mothers. We previously showed that DNE enhances the respiratory motor response to bath application of AMPA to the brainstem, although it was unclear which brainstem respiratory neurons
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