α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid
Structural formula | |||||||||||||
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Structural formula without stereochemistry | |||||||||||||
General | |||||||||||||
Surname | α-Amino-3-hydroxy-5-methylisoxazole-4-propionic acid | ||||||||||||
other names |
AMPA |
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Molecular formula | C 7 H 10 N 2 O 4 | ||||||||||||
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properties | |||||||||||||
Molar mass | 186.17 g mol −1 | ||||||||||||
Physical state |
firmly |
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safety instructions | |||||||||||||
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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 .