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K2389

Sigma-Aldrich

Kainic acid monohydrate

≥98% (HPLC), from Digenea simplex

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Synonym(s):
2-Carboxy-3-carboxymethyl-4-isopropenylpyrrolidine
Empirical Formula (Hill Notation):
C10H15NO4 · H2O
CAS Number:
58002-62-3
Molecular Weight:
231.25
MDL number:
MFCD00150833
UNSPSC Code:
12352106
PubChem Substance ID:
24724520
NACRES:
NA.77

biological source

Digenea simplex

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

SMILES string

O.CC(=C)[C@H]1CN[C@@H]([C@H]1CC(O)=O)C(O)=O

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-SLGZUKMRSA-N

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Application

Kainic acid monohydrate has been used:
  • As a convulsant to induce epileptogenesis and epilepsy in mice.
  • To stimulate in vitro excitotoxic trauma in spiral ganglion neurons on inner hair cells.
  • To induce seizures in rat model.
  • To induce status epilepticus in adult male Wistar rats.

Biochem/physiol Actions

Ionotropic glutamate receptors form ion channels, and conduct Na+ and K+ fluxes. The receptors possess an agonist binding site and it encounters a conformational change upon agonist binding to it. Kainate gated channels participate in glutamate-induced excitatory postsynaptic neuronal potential.
Kainic acid monohydrate is an agonist at the kainate class of ionotropic glutamate receptors, which induces seizures and neurodegeneration in vivo and is used to induce experimental epilepsy in rodents and study the mechanisms of excitation-induced neuronal apoptosis.

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Flash Point(F)

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Flash Point(C)

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Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Urokinase-type plasminogen activator deficiency has little effect on seizure susceptibility and acquired epilepsy phenotype but reduces spontaneous exploration in mice
Rantala J, et al.
Epilepsy & Behavior : E&B, 42, 117-128 (2015)
Adeno-associated viral vector-induced overexpression of neuropeptide Y Y2 receptors in the hippocampus suppresses seizures
Woldbye David PD, et al.
Brain, 133(9), 2778-2788 (2010)
Combined gene overexpression of neuropeptide Y and its receptor Y5 in the hippocampus suppresses seizures
Gotzsche CR, et al.
Neurobiology of Disease, 45(1), 288-296 (2012)
Antti M Airaksinen et al.
Epilepsia, 53(7), 1245-1253 (2012-06-14)
To investigate how kainic acid-induced epileptiform activity is related to hemodynamic changes probed by blood oxygenation level-dependent functional magnetic resonance imaging (BOLD fMRI). Epileptiform activity was induced with kainic acid (KA) (10 mg/kg, i.p.), and simultaneous fMRI at 7 Tesla
Isabel San Martín Molina et al.
Frontiers in neuroscience, 16, 944432-944432 (2022-08-16)
Non-invasive magnetic resonance imaging (MRI) methods have proved useful in the diagnosis and prognosis of neurodegenerative diseases. However, the interpretation of imaging outcomes in terms of tissue pathology is still challenging. This study goes beyond the current interpretation of in
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