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Details

Stereochemistry RACEMIC
Molecular Formula C7H10N2O4
Molecular Weight 186.1653
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMPA

SMILES

CC1=C(CC(N)C(O)=O)C(=O)NO1

InChI

InChIKey=UUDAMDVQRQNNHZ-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C7H10N2O4
Molecular Weight 186.1653
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

(±)-α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) is a selective agonist of AMPA subtype of glutamate receptors. It is used in biological studies as an experimental tool.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
(RS)-alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid: wet dog shakes, catalepsy and body temperature changes in rats.
1981 Oct

Sample Use Guides

in rats (microinjected into the lateral brain ventricle): (α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) produced generalized myoclonic seizures, short lasting hypoactivity followed by hyperactivity and hyperthermia when low doses were injected (0.25-1.0 microgram). When AMPA was injected at higher doses (1.5-5.0 microgram) it produced generalized myoclonic seizures, a hypoactive phase and hypothermia rapidly followed by hyperthermia
Route of Administration: Other
In Vitro Use Guide
Binding of [3H]AMPA (α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) to rat brain membranes was investigated. Computer-aided Scatchard analysis of the binding data, as determined by using L-glutamic acid (L-GLU) to define nonspecific binding, suggested the presence of two independent binding sites, with KDS of 9 and 2440 nM, respectively. Additional freezing, thawing and washing sequences gave membranes with only one binding site, with a KD of 278 nM. [3H]AMPA binding exhibited the highest level in striatal membranes.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:35:10 GMT 2023
Edited
by admin
on Sat Dec 16 08:35:10 GMT 2023
Record UNII
J090588E6X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMPA
MI  
Common Name English
ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID
Systematic Name English
.GAMMA.-AMINO-3-HYDROXY-5-METHYLISOXAZOLE-4-PROPIONIC ACID
Common Name English
DL-.ALPHA.-AMINO-3-HYDROXY-5-METHYLISOXAZOLE-4-PROPIONIC ACID
Common Name English
(±)-.ALPHA.-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID
Systematic Name English
AMPA [MI]
Common Name English
4-ISOXAZOLEPROPANOIC ACID, .ALPHA.-AMINO-2,3-DIHYDRO-5-METHYL-3-OXO-
Common Name English
Code System Code Type Description
FDA UNII
J090588E6X
Created by admin on Sat Dec 16 08:35:10 GMT 2023 , Edited by admin on Sat Dec 16 08:35:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID20868301
Created by admin on Sat Dec 16 08:35:10 GMT 2023 , Edited by admin on Sat Dec 16 08:35:10 GMT 2023
PRIMARY
PUBCHEM
1221
Created by admin on Sat Dec 16 08:35:10 GMT 2023 , Edited by admin on Sat Dec 16 08:35:10 GMT 2023
PRIMARY
CHEBI
28812
Created by admin on Sat Dec 16 08:35:10 GMT 2023 , Edited by admin on Sat Dec 16 08:35:10 GMT 2023
PRIMARY
CAS
77521-29-0
Created by admin on Sat Dec 16 08:35:10 GMT 2023 , Edited by admin on Sat Dec 16 08:35:10 GMT 2023
PRIMARY
MERCK INDEX
m1845
Created by admin on Sat Dec 16 08:35:10 GMT 2023 , Edited by admin on Sat Dec 16 08:35:10 GMT 2023
PRIMARY Merck Index
Related Record Type Details
POSITIVE ALLOSTERIC MODULATOR->TARGET
TARGET -> AGONIST
LABELED -> NON-LABELED