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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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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
Pricing and availability is not currently available.

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
114K3782

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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
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
Frederic Lanore et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(49), 17882-17893 (2012-12-12)
The grik2 gene, coding for the kainate receptor subunit GluK2 (formerly GluR6), is associated with autism spectrum disorders and intellectual disability. Here, we tested the hypothesis that GluK2 could play a role in the appropriate maturation of synaptic circuits involved
Mado Lemieux et al.
The Journal of cell biology, 198(6), 1055-1073 (2012-09-12)
The processing of excitatory synaptic inputs involves compartmentalized dendritic Ca(2+) oscillations. The downstream signaling evoked by these local Ca(2+) transients and their impact on local synaptic development and remodeling are unknown. Ca(2+)/calmodulin-dependent protein kinase II (CaMKII) is an important decoder
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
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