Quisqualic acid

Names

[ Name ]:
Quisqualic acid

[Synonym ]:
L-Alanine, 3-(3-hydroxy-5-oxo-1,2,4-oxadiazol-2(5H)-yl)-
L-Quisqualic acid
L-Alanine, 3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)-
1,2,4-Oxadiazolidine-2-propanoic acid, α-amino-3,5-dioxo-, (S)-
MFCD00069337
3-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine
b-(3,5-Dioxo-1,2,4-oxodiazolidin-2-yl)-L-alanine
L-(+)-a-Amino-3,5-dioxo-1,2,4-oxadiazolidine-2-propanoic Acid
(L)-(+)-a-Amino-3,5-dioxo-1,2,4-oxadiazolidine-2-propanoic acid
Quisqualic acid
3-(3-Hydroxy-5-oxo-1,2,4-oxadiazol-2(5H)-yl)-L-alanine
β-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine
L-Quisqualic acid,(L)-(+)-α-Amino-3,5-dioxo-1,2,4-oxadiazolidine-2-propanoicacid
(S)-a-Amino-3,5-dioxo-1,2,4-oxadiazolidine-2-propanoic Acid

Biological Activity

[Description]:

Quisqualic acid (L-Quisqualic acid), a natural analog of glutamate, is a potent and pan two subsets (iGluR and mGluR) of excitatory amino acid (EAA) agonist with an EC50 of 45 nM and a Ki of 10 nM for mGluR1R. Quisqualic acid is isolated from the fruits of Quisqualis chinensis[1][2].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR

Signaling Pathways >> GPCR/G Protein >> mGluR

Research Areas >> Neurological Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

[Target]

mGluR1R:45 nM (EC50)

mGluR1R:10 nM (Ki)

mGluR2R:108 μM (IC50)

mGluR2R:113 μM (Ki)

mGluR4R:593 μM (IC50)

mGluR4R:112 μM (Ki)

[In Vitro]

Quisqualic acid is an agonist of AMPA and metabotropic glutamate receptors. Quisqualic acid activates mGluR2R (EC50=108 μM; Ki=113 μM) and mGluR4R (EC50=593 μM; Ki=112 μM)[1].

[References]

[1]. Hugues-Olivier Bertrand, et al. Common and Selective Molecular Determinants Involved in Metabotopic Glutamate Receptor Agonist Activity. J Med Chem. 2002 Jul 18;45(15):3171-83.

[2]. H Bräuner-Osborne, et al. Ligands for Glutamate Receptors: Design and Therapeutic Prospects. J Med Chem. 2000 Jul 13;43(14):2609-45.

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Boiling Point ]:
405.9±55.0 °C at 760 mmHg

[ Melting Point ]:
185-187ºC dec.

[ Molecular Formula ]:
C₅H₇N₃O₅

[ Molecular Weight ]:
189.126

[ Flash Point ]:
199.3±31.5 °C

[ Exact Mass ]:
189.038574

[ PSA ]:
131.32000

[ LogP ]:
-1.85

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.726

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Related Compounds

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