A natural analog of glutamate
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L-Quisqualic Acid

Item No. 20211

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
αS-amino-3,5-dioxo-1,2,4-oxadiazolidine-2-propanoic acid
CAS Number
52809-07-1
Molecular Formula
C5H7N3O5
Formula Weight
189.1
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Water: 25 mM
SMILES
O=C1NC(N(C[C@@H](C(O)=O)N)O1)=O
InChi Code
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
InChi Key
ASNFTDCKZKHJSW-REOHCLBHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $62

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    5 mg

    $120

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    10 mg

    $207

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    25 mg

    $442

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    Product Description

    L-Quisqualic acid is a natural analog of glutamate that acts as an agonist at AMPA-selective and metabotropic glutamate receptors (EC50s = 170, 10, 40, and 29 nM at GluR-A, mGluR1, mGluR3, and mGluR5, respectively), as well as the ionotropic kainate receptor (GRIK4; Ki = 6.43 nM).1,2,3,4,5,6 L-Quisqualic acid is used to study receptor dynamics and as an excitotoxin to selectively destroy neurons in the brain or spinal cord.7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schoepp, D.D., Jane, D.E., and Monn, J.A. Pharmacological agents acting at subtypes of metabotropic glutamate receptors. Neuropharmacology 38(10), 1431-1476 (1999).

    2. Bräuner-Osborne, H., Egebjerg, J., Nielsen, E.O., et al. Ligands for glutamate receptors: Design and therapeutic prospects. J. Med. Chem. 43(14), 2609-2645 (2000).

    3. Bertrand, H.-O., Besis, A.-S., Pin, J.-P., et al. Common and selective molecular determinants involved in metabotopic glutamate receptor agonist activity. J. Med. Chem. 45(15), 3171-3183 (2002).

    4. Kamboj, R.K., Schoepp, D.D., Nutt, S., et al. Molecular cloning, expression, and pharmacological characterization of humEAA1, a human kainate receptor subunit. J.Neurochem. 62(1), 1-9 (1994).

    5. Mutel, V., Ellis, G.J., Adam, G., et al. Characterization of [3H]quisqualate binding to recombinant rat metabotropic glutamate 1a and 5a receptors and to rat and human brain sections. J. Neurochem. 75(6), 2590-2601 (2000).

    6. Uchino, S., Sakimura, K., Nagahari, K., et al. Mutations in a putative agonist binding region of the AMPA-selective glutamate receptor channel. FEBS Lett. 308(3), 253-257 (1992).

    7. Lee, J.-W., Furmanski, O., Castellanos, D.A., et al. Prolonged nociceptive responses to hind paw formalin injection in rats with a spinal cord injury. Neurosci. Lett. 439(2), 212-215 (2008).

    8. Muir, J.L., Page, K.J., Sirinathsinghji, D.J.S., et al. Excitotoxic lesions of basal forebrain cholinergic neurons: effects on learning, memory and attention. Behav. Brain Res. 57(2), 123-131 (1993).