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Merck

A0326

(S)-AMPA

≥97%, AMPA receptor agonist, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C7H10N2O4
CAS Number:
83643-88-3
Molecular Weight:
186.17
UNSPSC Code:
12352200
PubChem Substance ID:
24890421
NACRES:
NA.77
MDL number:
MFCD00672630

Key Documents

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Product Name

(S)-AMPA, ≥97%

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

assay

≥97%

form

powder

Quality Level

100

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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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.
Potent agonist at the AMPA subclass of ionotropic glutamate receptors; active enantiomer.

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.

General description

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC4284
BCBZ5768
BCBW2555
BCBS3621V
BCBS3621

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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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