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Key Documents

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A0326

Sigma-Aldrich

(S)-AMPA

≥97%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C7H10N2O4
Número de CAS:
83643-88-3
Peso molecular:
186.17
MDL number:
MFCD00672630
UNSPSC Code:
12352200
PubChem Substance ID:
24890421
NACRES:
NA.77

Quality Level

100

assay

≥97%

form

powder

SMILES string

Cc1onc(O)c1C[C@H](N)C(O)=O

InChI

1S/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1

InChI key

UUDAMDVQRQNNHZ-YFKPBYRVSA-N

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)

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General description

AMPA (α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) activates excitatory postsynaptic currents (EPSC).

Application

(S)-AMPA has also been used to activate rostromedial tegmental nucleus (RMTg), to study aversive conditioning in relation with cocaine-induced avoidance behaviors in mice.
(S)-AMPA has been used to selectively eliminate the neural cochlear component of adult barn owls by destroying afferent synapses.

Biochem/physiol Actions

Active enantiomer of (RS)-AMPA zwitterion. Potent agonist at the AMPA subclass of ionotropic glutamate receptors.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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(±)-AMPA hydrobromide ≥98% (HPLC)

Sigma-Aldrich

A9111

(±)-AMPA hydrobromide

Derek Bowie
The Journal of physiology, 590(1), 49-61 (2011-11-23)
AMPA-type ionotropic glutamate receptors (iGluRs) represent the major excitatory neurotransmitter receptor in the developing and adult vertebrate CNS. They are crucial for the normal hardwiring of glutamatergic circuits but also fine tune synaptic strength by cycling into and out of
Interneuron Diversity series: Fast in, fast out-temporal and spatial signal processing in hippocampal interneurons
Jonas P, et al.
Trends in Neurosciences, 27(1), 30-40 (2004)
Evoked cochlear potentials in the barn owl
Koppl C and Gleich O
J. Comp. Physiol., 193(6), 601-612 (2007)
Penelope J Brockie et al.
Neuron, 80(1), 129-142 (2013-10-08)
The strength of synaptic communication at central synapses depends on the number of ionotropic glutamate receptors, particularly the class gated by the agonist AMPA (AMPARs). Cornichon proteins, evolutionarily conserved endoplasmic reticulum cargo adaptors, modify the properties of vertebrate AMPARs when
J Lauridsen et al.
Journal of medicinal chemistry, 28(5), 668-672 (1985-05-01)
The syntheses of (RS)-alpha-amino-3-hydroxy-5-tert-butyl-4-isoxazolepropionic acid (9, ATPA), (alpha-RS, beta-RS)-alpha-amino-beta-methyl-3-hydroxy-5-isoxazolepropionic acid (8), (RS)-alpha-amino-3-hydroxy-5-isoxazolebutyric acid (15a), and (RS)-alpha-amino-3-hydroxy-5-isoxazolevaleric acid (15b) are described. The compounds were tested in vitro together with (RS)-alpha-amino-3-hydroxy-5-(bromomethyl)-4-isoxazolepropionic acid (ABPA) as inhibitors of the binding of radioactive-labeled (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
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