An L-glutamate analog with neuroexcitatory activities
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(−)-(α)-Kainic Acid (hydrate)

Item No. 78050

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-carboxy-4S-(1-methylethenyl)-3S-pyrrolidineacetic acid, monohydrate
CAS Number
58002-62-3
Molecular Formula
C10H15NO4 • H2O
Formula Weight
231.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 50 mg/ml
SMILES
[H]N1C[C@H](C(C)=C)[C@H](CC(O)=O)[C@H]1C(O)=O.O
InChi Code
InChI=1S/C10H15NO4.H2O/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13;/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15);1H2/t6-,7+,9?;/m0./s1
InChi Key
FZNZRJRSYLQHLT-AQLFBIHGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $87

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    10 mg

    $165

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    25 mg

    $370

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    50 mg

    $653

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    Product Description

    (−)-(α)-Kainic acid is a cyclic analog of L-glutamate originally isolated from D. simplex that has neuroexcitatory activities.1 It binds to the homomeric kainate receptors GluK1, GluK2, GluK3, GluK4, and GluK5 (Kis = 75.9, 12.7, 32.8, 4.7, and 15 nM, respectively).2 (−)-(α)-Kainic acid (5 mM) induces calcium influx and membrane depolarization, as well as glutamate release, in rat brain synaptosomes.3 It induces chromatin condensation and nuclear membrane fragmentation, markers of apoptosis, in primary neonatal cerebellar granule neurons when used at a concentration of 100 µM.4 Intracerebroventricular administration of (−)-(α)-kainic acid induces convulsive behavior in rats (ED50 = 0.51 nmol/animal) and induces seizures in mice with a 50% convulsive dose (CD50) value of 0.39 nmol/animal.5 It has been commonly used to induce seizures in rodents.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Reddy, N.K., and Chandrasekhar, S. Total synthesis of (−)-a-kainic acid via chirality transfer through Ireland-Claisen rearrangement. The Journal of Organic Chemistry 78(7), 3355-3360 (2013).

    2. Sagot, E., Pickering, D.S., Pu, X., et al. Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: New insight into the structure - activity relation of ionotropic glutamate receptor subtypes 5, 6, and 7. J. Med. Chem. 51(14), 4093-4103 (2008).

    3. Pastuszko, A., Wilson, D.F., and Erecińska, M. Effects of kainic acid in rat brain synaptosomes: The involvement of calcium. J. Neurochem. 43(3), 747-754 (1984).

    4. Simonian, N.A., Getz, R.L., Leveque, J.C., et al. Kainic acid induces apoptosis in neurons. Neuroscience 75(4), 1047-1055 (1996).

    5. Chiamulera, C., Costa, S., Valerio, E., et al. Domoic acid toxicity in rats and mice after intracerebroventricular administration: Comparison with excitatory amino acid agonists. Pharmacol. Toxicol. 70(2), 115-120 (1992).

    6. Wang, Q., Yu, S., Simonyi, A., et al. Kainic acid-mediated excitotoxicity as a model for neurodegeneration. Mol. Neurobiol. 31(1-3), 3-16 (2005).

    7. Domin, H., Zieba, B., Golembiowska, K., et al. Neuroprotective potential of mGluR5 antagonist MTEP: Effects on kainate-induced excitotoxicity in the rat hippocampus. Pharmacol. Rep. 62(6), 1051-1061 (2010).