A6816

(±)-AMPA

Name: (±)-AMPA
Brand: SIGMA
Price: 748 ILS

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

Key Documents

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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	A263	A9111	A0326
Sigma-Aldrich A6816 (±)-AMPA	Sigma-Aldrich A263 ATPA	Sigma-Aldrich A9111 (±)-AMPA hydrobromide	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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Developmental regulation and activity-dependent maintenance of GABAergic presynaptic inhibition onto rod bipolar cell axonal terminals.

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

Local Signals in Mouse Horizontal Cell Dendrites.

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

Comparison of excitotoxic profiles of ATPA, AMPA, KA and NMDA in organotypic hippocampal slice cultures.

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

CNQX and AMPA inhibit electrical synaptic transmission: a potential interaction between electrical and glutamatergic synapses.

Qin Li et al.

Brain research, 1228, 43-57 (2008-07-08)

Electrical synapses play an important role in signaling between neurons and the synaptic connections between many neurons possess both electrical and chemical components. Although modulation of electrical synapses is frequently observed, the cellular processes that mediate such changes have not

Calcium-permeable α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors trigger neuronal nitric-oxide synthase activation to promote nerve cell death in an Src kinase-dependent fashion.

Renato Socodato et al.

The Journal of biological chemistry, 287(46), 38680-38694 (2012-09-21)

In the retina information decoding is dependent on excitatory neurotransmission and is critically modulated by AMPA glutamate receptors. The Src-tyrosine kinase has been implicated in modulating neurotransmission in CNS. Thus, our main goal was to correlate AMPA-mediated excitatory neurotransmission with

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(±)-AMPA