Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H15NO4.H2O |
Molecular Weight | 231.2457 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CC(=C)[C@H]1CN[C@@H]([C@H]1CC(O)=O)C(O)=O
InChI
InChIKey=FZNZRJRSYLQHLT-SLGZUKMRSA-N
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
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C10H15NO4 |
Molecular Weight | 213.2304 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21127706Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/10821708 | https://www.ncbi.nlm.nih.gov/pubmed/28229936 | https://www.ncbi.nlm.nih.gov/pubmed/28222432 | https://www.ncbi.nlm.nih.gov/pubmed/28293167 | https://www.ncbi.nlm.nih.gov/pubmed/28303499
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21127706
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/10821708 | https://www.ncbi.nlm.nih.gov/pubmed/28229936 | https://www.ncbi.nlm.nih.gov/pubmed/28222432 | https://www.ncbi.nlm.nih.gov/pubmed/28293167 | https://www.ncbi.nlm.nih.gov/pubmed/28303499
Kainic acid (kainate) is a natural marine acid present in some seaweed. Kainic acid is a potent neuroexcitatory amino acid that acts by activating receptors for glutamate, the principal excitatory neurotransmitter in the central nervous system. Kainic acid is commonly injected into laboratory animal models to study the effects of experimental ablation. Kainic acid is a direct agonist of the glutamic kainate receptors and large doses of concentrated solutions produce immediate neuronal death by overstimulating neurons to death. Such damage and death of neurons is referred to as an excitotoxic lesion. Thus, in large, concentrated doses kainic acid can be considered a neurotoxin, and in small doses of dilute solution kainic acid will chemically stimulate neurons. Kainic acid is utilised in primary neuronal cell cultures and acute brain slice preparations [5] to study of the physiological effect of excitotoxicity and assess the neuroprotective capabilities of potential therapeutics. Kainic acid is a potent central nervous system excitant that is used in epilepsy research to induce seizures in experimental animals, at a typical dose of 10–30 mg/kg in mice. In addition to inducing seizures, kainic acid is excitotoxic and epileptogenic. Kainic acid induces seizures via activation of kainate receptors containing the GluK2 subunit and also through activation of AMPA receptors, for which it serves as a partial agonist.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3774232
Curator's Comment: KAINIC ACID cannot penetrate blood brain barrier, but active in brain of experimental animals
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10821708 |
8.0 nM [IC50] | ||
Target ID: CHEMBL3683 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10821708 |
32.0 nM [Ki] | ||
Target ID: CHEMBL3684 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10821708 |
10.0 nM [Ki] | ||
Target ID: CHEMBL1918 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10821708 |
177.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Stimulation of metabotropic but not ionotropic glutamatergic receptors in the nucleus accumbens is required for the D-amphetamine-induced release of functional dopamine. | 2001 |
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Kainate-induced seizures alter protein composition and N-methyl-D-aspartate receptor function of rat forebrain postsynaptic densities. | 2001 |
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Epileptiform activity and EPSP-spike potentiation induced in rat hippocampal CA1 slices by repeated high-K(+): involvement of ionotropic glutamate receptors and Ca(2+)/calmodulin-dependent protein kinase II. | 2001 |
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The effects of GABA(B) receptor activation on spontaneous and evoked activity in the dentate gyrus of kainic acid-treated rats. | 2001 |
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Role of AMPA and GluR5 kainate receptors in the development and expression of amygdala kindling in the mouse. | 2001 |
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Methods for inducing neuronal loss in preweanling rats using intracerebroventricular infusion of kainic acid. | 2001 Apr |
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Consolidation of transient ionotropic glutamate signals through nuclear transcription factors in the brain. | 2001 Apr |
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Transient increase in the high affinity [3H]-L-glutamate uptake activity during in vitro development of hippocampal neurons in culture. | 2001 Apr |
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Kainate receptor activation induces mixed lineage kinase-mediated cellular signaling cascades via post-synaptic density protein 95. | 2001 Apr 6 |
|
Role of non-NMDA receptors in vasopressin and oxytocin release from rat hypothalamo-neurohypophysial explants. | 2001 Feb |
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Regulation of X-chromosome-linked inhibitor of apoptosis protein in kainic acid-induced neuronal death in the rat hippocampus. | 2001 Feb |
|
Time sequence and types of memory deficits after experimental status epilepticus. | 2001 Feb |
|
Collapse of extracellular glutamate regulation during epileptogenesis: down-regulation and functional failure of glutamate transporter function in rats with chronic seizures induced by kainic acid. | 2001 Feb |
|
Plasminogen activator inhibitor-1 in cardiovascular cells: rapid induction after injecting mice with kainate or adrenergic agents. | 2001 Feb 1 |
|
Changes in striatal electroencephalography and neurochemistry induced by kainic acid seizures are modified by dopamine receptor antagonists. | 2001 Feb 16 |
|
Protein deimination in the rat brain after kainate administration: citrulline-containing proteins as a novel marker of neurodegeneration. | 2001 Feb 16 |
|
A spontaneous recurrent seizure-related Rattus NSF gene identified by linker capture subtraction. | 2001 Feb 19 |
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Immunocytochemical localization of kainate-selective glutamate receptor subunits GluR5, GluR6, and GluR7 in the cat retina. | 2001 Feb 2 |
|
NADPH diaphorase activity in the rabbit retina is modulated by glutamatergic pathways. | 2001 Feb 26 |
|
Reversible and irreversible damage to cochlear afferent neurons by kainic acid excitotoxicity. | 2001 Feb 5 |
|
Brain-derived neurotrophic factor mediates an excitoprotective effect of dietary restriction in mice. | 2001 Jan |
|
Changes in nitric oxide synthesis and epileptic activity in the contralateral hippocampus of rats following intrahippocampal kainate injection. | 2001 Jan |
|
Metabotropic glutamate receptors modify ionotropic glutamate responses in neocortical pyramidal cells and interneurons. | 2001 Jan |
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The role of RNA editing of kainate receptors in synaptic plasticity and seizures. | 2001 Jan |
|
Kainate receptors are involved in short- and long-term plasticity at mossy fiber synapses in the hippocampus. | 2001 Jan |
|
Calcitonin potentiates oxygen-glucose deprivation-induced neuronal death. | 2001 Jan |
|
Dendritic but not somatic GABAergic inhibition is decreased in experimental epilepsy. | 2001 Jan |
|
Role of dorsal raphe neurons in paradoxical sleep generation in the cat: no evidence for a serotonergic mechanism. | 2001 Jan |
|
Nucleus raphé obscurus modulates hypoglossal output of neonatal rat in vitro transverse brain stem slices. | 2001 Jan |
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Protective effects of dietary docosahexaenoic acid against kainate-induced retinal degeneration in rats. | 2001 Jan |
|
Expression of brain-derived neurotrophic factor in cortical neurons is regulated by striatal target area. | 2001 Jan 1 |
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Presynaptic kainate receptors regulate spinal sensory transmission. | 2001 Jan 1 |
|
Involvement of NMDA and AMPA/kainate receptors in the effects of endogenous glutamate on extracellular concentrations of dopamine and GABA in the nucleus accumbens of the awake rat. | 2001 Jan 15 |
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Kainate-induced K+ efflux and plasma membrane depolarization in cultured cerebellar granule cells. | 2001 Jan 22 |
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Calcium inhibits willardiine-induced responses in kainate receptor GluR6(Q)/KA-2. | 2001 Jan 22 |
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In vivo, the direct and seizure-induced neuronal cytotoxicity of kainate and AMPA is modified by the non-competitive antagonist, GYKI 52466. | 2001 Jan 26 |
|
Differential changes in neuropeptide Y and nicotinamide adenine dinucleotide phosphate-diaphorase-positive neurons in rat hippocampus after kainic acid-induced seizure. | 2001 Jan 26 |
|
The effects of glutamate receptor agonists on neurotensin release using in vivo microdialysis. | 2001 Jan 5 |
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Regulation of rat hippocampal neural cadherin in the kainic acid induced seizures. | 2001 Jan 5 |
|
Involvement of adrenal medulla grafts in the open field behavior. | 2001 Jun |
|
Effects of glutathione depletion by 2-cyclohexen-1-one on excitatory amino acids-induced enhancement of activator protein-1 DNA binding in murine hippocampus. | 2001 Mar |
|
Kainate receptors keep the excitement high. | 2001 Mar |
|
Cortical and striatal neuronal cultures of the same embryonic origin show intrinsic differences in glutamate receptor expression and vulnerability to excitotoxicity. | 2001 Mar |
|
Tissue plasminogen activator protects hippocampal neurons from oxygen-glucose deprivation injury. | 2001 Mar 1 |
|
Domain interactions regulating ampa receptor desensitization. | 2001 Mar 15 |
|
Identification of the amino acids on a neuronal glutamate receptor recognized by an autoantibody from a patient with paraneoplastic syndrome. | 2001 Mar 15 |
|
Neostriatal stimulation activates tongue-protruder muscle, but not tongue-retractor or facial muscles: an electrical and chemical microstimulation study in rats. | 2001 Mar 2 |
|
Intrathecal magnesium sulfate attenuates algogenic behavior and spinal amino acids release after kainic acid receptor activation in rats. | 2001 Mar 30 |
|
Rapid kindling of the hippocampus protects against neural damage resulting from status epilepticus. | 2001 Mar 5 |
|
Blockade of AMPA/kainate receptors can either decrease or increase the survival of cultured neocortical cells depending on the stage of maturation. | 2001 May |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28303499
The chronic epileptic models were induced by the microinjection of kainic acid (KA) into rats’ hippocampus. The rat anesthetized with 10% chloralhydrate (0.35 ml/g) by intraperitoneal injection (i.p.) were fixed on the stereotactic apparatus. A hole was drilled in the skull with dental reamers. Using a micro-injector, seizure was induced with stereotactic-injection 3 μL KA (0.5 mg/ml) into the CA3 region of the left hippocampus, 5.0 mm posterior to the bregma, 5.0 mm left lateral from the mid-line, and 5.0 mm deep from the dura.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28293167
N2a cells viability were assayed by MTT after treatment with 0, 25, 50, 100 mM Kainic acid (KA). To observe the changes in the mitochondrial morphology
in N2a cells, the KA and/or melatonin-treated N2a cells were incubated with the MitoTracker Red CMXRos probe (250 nM) (Invitrogen, Carlsbad, CA, USA) for 30 min at 37OC. After being washed three times in cold PBS, the cells were visualized under a Nikon C2 confocal laser scanning microscope (Nikon, Tokyo, Japan) with excitation of 579 nm and emission greater than 599 nm. For morphological quantification in neurites, z-sections were merged (using maximal projection) and the entire length (from tip to tip) of MitoTracker Red labeled mitochondria of neurites was measured. In cell bodies, mitochondria length was measured in each z-section of the entire soma. Quantification of mitochondria length was performed by using ImageJ software as previously described . The number of mitochondria was counted in control N2a cells (n = 50) and experimental groups (n = 40).
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 06:02:25 GMT 2023
by
admin
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Record UNII |
I519JC63XY
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Record Status |
Validated (UNII)
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Record Version |
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ANHYDROUS->SOLVATE | |||
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ACTIVE MOIETY |