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Merck

A6816

(±)-AMPA

solid

Synonym(s):

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

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€154.00

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€512.00

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€820.00

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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

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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)

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This Item
A263A9111A0326
(±)-AMPA solid

Sigma-Aldrich

A6816

(±)-AMPA

ATPA solid

Sigma-Aldrich

A263

ATPA

(±)-AMPA hydrobromide ≥98% (HPLC)

Sigma-Aldrich

A9111

(±)-AMPA hydrobromide

(S)-AMPA ≥97%

Sigma-Aldrich

A0326

(S)-AMPA

form

solid

form

solid

form

powder

form

powder

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, DMSO: 4.3 mg/mL

solubility

DMSO: 10 mg/mL, H2O: 2.5 mg/mL

solubility

H2O: ≥10 mg/mL

solubility

-

color

white

color

white

color

off-white to light tan

color

-

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

Gene Information

-

Gene Information

human ... GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK1(2897)
mouse ... Gria1(14799)
rat ... Gria1(50592), Gria2(29627), Gria3(29628), Gria4(29629), Grik1(29559), Grik2(54257), Grik4(24406), Grin2a(24409), Grin2b(24410), Grm6(24419)

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 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

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Certificates of Analysis (COA)

Lot/Batch Number
0000070063
0000070064
0000063010
0000063025
0000063014

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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
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
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
Laura A DeNardo et al.
Neuron, 76(4), 762-775 (2012-11-28)
An important organizing feature of the CNS is that individual neurons receive input from many different sources. Independent regulation of synaptic input is critical for the function and adaptive responses of the nervous system, but the underlying molecular mechanisms are not
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