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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

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
  • to test its excitotoxic effects in hippocampal slice cultures
  • in retinal horizontal cells (HCs) culture to test its effect on Ca2+ signals

Biochem/physiol Actions

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Timm Schubert et al.
Neuron, 78(1), 124-137 (2013-04-16)
Presynaptic inhibition onto axons regulates neuronal output, but how such inhibitory synapses develop and are maintained in vivo remains unclear. Axon terminals of glutamatergic retinal rod bipolar cells (RBCs) receive GABAA and GABAC receptor-mediated synaptic inhibition. We found that perturbing GABAergic
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
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
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