α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid

Structural formula
	Structural formula without stereochemistry
General
Surname	α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid
other names	AMPA
Molecular formula	C 7 H 10 N 2 O 4
External identifiers / databases
PubChem	1221
ChemSpider	1184
Wikidata	Q66370552
properties
Molar mass	186.17 g mol −1
Physical state	firmly
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

α-Amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (frequently but ambiguously abbreviated as AMPA ) is a chemical compound from the group of synthetic non-proteinogenic amino acids .

Isomers

α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid is a chiral compound. There are two stereoisomers , ( S ) - and ( R ) -AMPA. Only ( S ) -AMPA has an effect on biological receptors , so this isomer is usually meant when AMPA is mentioned without any additional addition.

Isomers of ΑMPA
Surname	( S ) -AMPA	( R ) -AMPA
other names	L - (+) - AMPA	D - (-) - AMPA
Structural formula
CAS number	83643-88-3	83654-13-1
	77521-29-0 ( racemate )
PubChem	158397	6604707
	1221 (unspec.)
DrugBank	DB02057	-
	- (unspec.)
Wikidata	Q917803	Q27277614
	Q66370552 (unspec.)

properties

( S ) -AMPA is an agonist of the AMPA receptors , a subgroup of the ionotropic glutamate receptors that are also ion channels . After activation by the influx of sodium and potassium ions in neurons, it triggers an excitatory postsynaptic potential (EPSP). In electrical synapses , AMPA inhibits the transmission of an EPSP. After binding of AMPA to the AMPA receptor, clathrin-mediated endocytosis of the AMPA receptor occurs.

Individual evidence

↑ ^a ^b data sheet (±) -AMPA, solid at Sigma-Aldrich , accessed on November 29, 2018 ( PDF ).
^ Scott Brady: Basic Neurochemistry. Academic Press, 2012, ISBN 978-0-123-74947-5 , p. 1057 ( limited preview in Google Book Search).
↑ ^a ^b Q. Li, BD Burrell: CNQX and AMPA inhibit electrical synaptic transmission: a potential interaction between electrical and glutamatergic synapses. In: Brain Research . Volume 1228, September 2008, pp. 43-57, doi : 10.1016 / j.brainres.2008.06.035 , PMID 18601913 , PMC 2612578 (free full text).
↑ JW Lin, W. Ju, K. Foster, SH Lee, G. Ahmadian, M. Wyszynski, YT Wang, M. Sheng: Distinct molecular mechanisms and divergent endocytotic pathways of AMPA receptor internalization. In: Nature Neuroscience . Volume 3, Number 12, December 2000, pp. 1282-1290, doi : 10.1038 / 81814 , PMID 11100149 .

[Sigma-1] ta sheet (±) -AMPA, solid at Sigma-Aldrich , accessed on November 29, 2018 ( PDF ).

[books-NPqgM38h4LsC-1057-2] Scott Brady: Basic Neurochemistry. Academic Press, 2012, ISBN 978-0-123-74947-5 , p. 1057 ( limited preview in Google Book Search).

[Li-3] Q. Li, BD Burrell: CNQX and AMPA inhibit electrical synaptic transmission: a potential interaction between electrical and glutamatergic synapses. In: Brain Research . Volume 1228, September 2008, pp. 43-57, doi : 10.1016 / j.brainres.2008.06.035 , PMID 18601913 , PMC 2612578 (free full text).

[4] JW Lin, W. Ju, K. Foster, SH Lee, G. Ahmadian, M. Wyszynski, YT Wang, M. Sheng: Distinct molecular mechanisms and divergent endocytotic pathways of AMPA receptor internalization. In: Nature Neuroscience . Volume 3, Number 12, December 2000, pp. 1282-1290, doi : 10.1038 / 81814 , PMID 11100149 .