AMPA

Title: AMPA
CAS Registry Number: 77521-29-0
CAS Name: a-Amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid
Additional Names: a-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
Molecular Formula: C7H10N2O4
Molecular Weight: 186.17
Percent Composition: C 45.16%, H 5.41%, N 15.05%, O 34.38%
Literature References: Synthetic excitatory amino acid that characterizes a specific subset of ionotropic glutamate receptors in the CNS, consequently known as AMPA-receptors. The activity resides primarily in the L-isomer. Prepn: J. J. Hansen, P. Krogsgaard-Larsen, J. Chem. Soc. Perkin Trans. 1 1980, 1826; M. Begtrup, F. A. Slok, Synthesis 1993, 861. Characterization of neuroexcitatory activity: P. Krogsgaard-Larsen et al., Nature 284, 64 (1980). Resolution of enantiomers and stereospecific activity: J. J. Hansen et al., J. Med. Chem. 26, 901 (1983). Review of AMPA receptors: K. Borges, R. Dingledine, Prog. Brain Res. 116, 153-170 (1998); and potential for pharmacological intervention: G. J. Lees, Drugs 59, 33-78 (2000).
Properties: Crystals from water as the monohydrate, mp 252° (dec).
Melting point: mp 252° (dec)
Derivative Type: L-AMPA
CAS Registry Number: 83643-88-3
Additional Names: S-AMPA
Properties: Crystals from water + ethanol as the hydrate, gradual decomp above ~200°. [a]D28 -21 ±2° (c = 0.19 in water).
Optical Rotation: [a]D28 -21 ±2° (c = 0.19 in water)
Ampelopsin Amperozide Amphecloral Amphenidone Amphenone B

AMPA
AMPA.svg
Identifiers
CAS number 74341-63-2 N
PubChem 1221
ChemSpider 1184 YesY
DrugBank DB02057
KEGG C11033 YesY
MeSH AMPA
ChEMBL CHEMBL276815 N
Jmol-3D images Image 1
Properties
Molecular formula C7H10N2O4
Molar mass 186.17 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

AMPA (α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) is a compound that is a specific agonist for the AMPA receptor, where it mimics the effects of the neurotransmitter glutamate.[1]

There are several types of glutamatergic ion channels in the central nervous system including AMPA, kainic acid and N-methyl-D-aspartic acid (NMDA) channels. In the synapse, these receptors serve very different purposes. AMPA can be used experimentally to distinguish the activity of one receptor from the other in order to understand their differing functions.[2] AMPA generates fast excitatory postsynaptic potentials (EPSP).[1] AMPA activates AMPA receptors that are non-selective cationic channels allowing the passage of Na+ and K+ and therefore have an equilibrium potential near 0 mV.