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A6816

Sigma-Aldrich

(±)-AMPA

solid

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Synonym(s):
(±)-α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid hydrate
Empirical Formula (Hill Notation):
C7H10N2O4
Molecular Weight:
186.17
MDL number:
PubChem Substance ID:
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

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1 of 4

This Item
L131A263A9111
vibrant-m

A6816

(±)-AMPA

vibrant-m

L131

L-745,870 hydrochloride

vibrant-m

A263

ATPA

vibrant-m

A9111

(±)-AMPA hydrobromide

color

white

color

white

color

white

color

off-white to light tan

solubility

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

solubility

H2O: 0.2 mg/mL, ethanol: 1.4 mg/mL, 0.1 M HCl: 5.5 mg/mL

solubility

DMSO: 10 mg/mL, H2O: 2.5 mg/mL

solubility

H2O: ≥10 mg/mL

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)

Gene Information

human ... DRD4(1815)

Gene Information

human ... GRIK1(2897)
rat ... Gria1(50592), Grik1(29559), Grin2a(24409)

Gene Information

-

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

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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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
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
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
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
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

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