Quisqualic acid

Quisqualic acid is an agonist of the AMPA, kainate, and group I metabotropic glutamate receptors. It is one of the most potent AMPA receptor agonists known. It causes excitotoxicity and is used in neuroscience to selectively destroy neurons in the brain or spinal cord. Quisqualic acid occurs naturally in the seeds of Quisqualis species.

Quisqualic acid
Names
IUPAC name
3-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine
Systematic IUPAC name
(2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.164.809
EC Number
  • 637-070-2
KEGG
MeSH Quisqualic+Acid
UNII
  • InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1 Y
    Key: ASNFTDCKZKHJSW-REOHCLBHSA-N Y
  • InChI=1/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
    Key: ASNFTDCKZKHJSW-REOHCLBHBE
  • O=C1NC(=O)ON1C[C@H](N)C(=O)O
Properties
C5H7N3O5
Molar mass 189.126 g/mol
Melting point 187 to 188 °C (369 to 370 °F; 460 to 461 K) decomposes
Hazards
GHS labelling:
Warning
H302, H312, H332
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Research conducted by the USDA Agricultural Research Service, has demonstrated quisqualic acid is also present within the flower petals of zonal geranium (Pelargonium x hortorum) and is responsible for causing rigid paralysis of the Japanese beetle. Quisqualic acid is thought to mimic L-glutamic acid, which is a neurotransmitter in the insect neuromuscular junction and mammalian central nervous system.

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