CAS 77521-29-0 alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID (HCID 1221)

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Basic information

CAS: 77521-29-0
Standard SMILES: Cc1o[nH]c(=O)c1CC(N)C(=O)O
InChIKey: UUDAMDVQRQNNHZ-UHFFFAOYSA-N
Molecular formula: C7H10N2O4
Average molar mass: 186.17 g/mol
Monoisotopic mass: 186.0640568

Overview

(S)-AMPA is a non-proteinogenic alpha-amino acid.

Names & identifiers

Preferred name: alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID
IUPAC: 2-amino-3-(5-methyl-3-oxo-1,2-oxazol-4-yl)propanoic acid
English name: (RS)-AMPA
Molecular formula: C7H10N2O4
Molecular weight: 186.17

Names & synonyms

alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID4-Isoxazolepropanoic acid, alpha-amino-2,3-dihydro-5-methyl-3-oxo-RefChem:915477alpha Amino 3 hydroxy 5 methyl 4 isoxazolepropionic Acidampa77521-29-0(RS)-AMPA74341-63-2(R,S)-AMPAAMPA (pharmaceutical)(R,S)-A-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID2-amino-3-(5-methyl-3-oxo-2,3-dihydroisoxazol-4-yl)propanoic acid

Show more names

C13672AMPA HBR(RS)-AMPA hydrobromiAMPA (ZWITTERION) POTENT EXCITATORY AMI5-Methyl-3-hydroxy-α-aminoisoxazole-4-propionic acid2-AMINO-3-(3-HYDROXY-5-METHYLISOXAZOL-4-YL)PROPANOIC ACID2-Amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propanoic acid

2-Amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)-propionic acidalpha-Amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acidCHEMBL13378J090588E6XAMPA HYDRATEAMPA hydrobromide(+/-)-alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID2-amino-3-(5-methyl-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)propanoic acid

Properties

Computed structural properties

XLogP: -3.2
Topological polar surface area: 102 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 3
Heavy atoms: 13
Formal charge: 0
Complexity: 284

Experimental & physicochemical properties

Ionization Efficiency · 6 items

Positive

0.94

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Physicochemical properties

Melting point: 240 °C · 240 °C
Density: 1.386 · 1.386±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: 2 O: · H2O: 1.2 mg/mL
pka: 2.15 · 2.15±0.10(Predicted)
form: solid
color: white
Water Solubility: Soluble in water (10mM, gentle warming)
Stability: Hygroscopic
CAS DataBase Reference: 77521 · 77521-29-0
FDA UNII: 90588 E6X · J090588E6X
EPA Substance Registry System: -2 · .alpha.-Amino-2,3-dihydro-5-methyl-3-oxo-4-isoxazolepropanoic acid (77521-29-0)

Safety & regulation

Safety data

wgk: 3
hs_code: 2934999090
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H319-H335-H302+H312+H332-H315
Precautionary statements: P280

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs that bind to and activate excitatory amino acid receptors.

Applications · 2 items

UsesA potent and selective agonist of the excitatory neurotransmitter L-glutamic Acid. AMPA does not interfere with binding sites for kainic acid in vitro, and AMPA- induced neuronal excitation is not significantly affected by NMDA antagonists

UsesAMPA is the defining agonist for the AMPA subgroup of ionotropic glutamate receptors, which mediate excitatory neurotransmission. Because AMPA does not interfere with binding sites for kainic acid or NMDA , it can be used to distinguish AMPA receptor-specific activity that contributes to a neuronal response. (R,S)-AMPA contains an equal mixture of the active (S)-enantiomer and the inactive (R)-enantiomer.