ChemicalBook > CAS DataBase List > KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE

Product Name: KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE
CAS No.: 58002-62-3
Chemical Name: KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE
Synonyms: KAINIC ACID MONOHYDRATE;KAINIC ACID HYDRATE;(?)-(α)-Kainic Acid hydrate;(-)-Kainic acid monohydrate;(-)-KAINIC ACID, MONOHYDRATE;(-)-α-Kainic Acid Monohydrate;(-)-(α)-Kainic Acid (hydrate);(-)-Alpha-Kainic Acid Monohydrate;KAINIC ACID MONOHYDRATE, ISOLATED FROM D;kainic acid monohydrate from digenea simplex
CBNumber: CB5351307
Molecular Formula: C10H17NO5
Formula Weight: 231.25
MOL File: 58002-62-3.mol

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KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE Property

Melting point:: 250-252°C
RTECS: UX9665250
storage temp.: 2-8°C
solubility: H₂O: >10 mg/mL
form: solid
color: white
biological source: Digenea simplex
Water Solubility: H2O: soluble
Sensitive: Light Sensitive
InChI: InChI=1/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-;/s3
InChIKey: FZNZRJRSYLQHLT-JMDCRQGXNA-N
SMILES: C([C@@H]1[C@H](NC[C@@H]1C(=C)C)C(=O)O)C(=O)O.O |&1:1,2,5,r|

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Safety

Safety Statements: 22-24/25
WGK Germany: 3
F: 10
TSCA: No

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: K0250
Product name: Kainic acid monohydrate
Purity: ≥99% (TLC)
Packaging: 10mg
Price: $246.29
Updated: 2025/07/31

Sigma-Aldrich

Product number: K0250
Product name: Kainic acid monohydrate
Purity: ≥99% (TLC)
Packaging: 50mg
Price: $1180
Updated: 2025/07/31

Cayman Chemical

Product number: 78050
Product name: (-)-(α)-Kainic Acid (hydrate)
Purity: ≥98%
Packaging: 5mg
Price: $72
Updated: 2024/03/01

Cayman Chemical

Product number: 78050
Product name: (-)-(α)-Kainic Acid (hydrate)
Purity: ≥98%
Packaging: 10mg
Price: $135
Updated: 2024/03/01

Sigma-Aldrich

Product number: K2389
Product name: Kainic acid monohydrate
Purity: ≥98% (HPLC), from Digenea simplex
Packaging: 10mg
Price: $337.25
Updated: 2025/07/31

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KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE Chemical Properties,Usage,Production

Description

(−)-(α)-Kainic acid is a cyclic analog of L-glutamate originally isolated from D. simplex that has neuroexcitatory activities. It binds to the homomeric kainate receptors GluK1, GluK2, GluK3, GluK4, and GluK5 (K_is = 75.9, 12.7, 32.8, 4.7, and 15 nM, respectively). (−)-(α)-Kainic acid (5 mM) induces calcium influx and membrane depolarization, as well as glutamate release, in rat brain synaptosomes. 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. 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. It has been commonly used to induce seizures in rodents.

Uses

Kainic acid is used to study mechanisms of excitation-induced apoptosis and epilepsy.

Uses

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.

General Description

Kainic acid is an agonist for kainate-class ionotropic glutamate receptors. Kainate receptors directly gate ion channels and are generally excitatory. Excess stimulation by Kainic acid induces neurocytosis (apoptosis) and epileptic seizures.

Biochem/physiol Actions

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.

in vivo

Kainic acid can be used to create epilepsy models and can be administered systemically, into the hippocampus, or amygdala, and is reproducible in various species. The systemic Kainic acid model closely mimics the manifestations of human temporal lobe epilepsy. When injected at a dose of 5 nM into the neostriatum, substantia nigra, or cerebellum, over half of the Kainic acid disappears from the injection site and brain within 0.5 hours, with radioactivity detected in other brain regions at concentrations lower than 7 pmol/mg^[3]^[4]^[6].

Induction of epilepsy model^[5]

Background

Kainic acid, an analog of L-glutamate and an ionotropic KA receptor agonist, can damage hippocampal pyramidal neurons.

Specific Modeling Methods

Mice: C57BL/6J ? male ? 7 weeks old ? 22 g body weight
Administration: 10 μg in 5 μL ? i.c.v.

Note

(1) The right lateral brain ventricle is localized with a stereotactic instrument.
(2) After the operation, skin was sutured, and keep the mice under a warming place until they wake up.
(3) 48 hours after lateral ventricle injection, the mice are anaesthetized using Isoflurane and then sequentially intracardially perfused with saline and PFA (4%, 30 mL). Rapidly remove The mouse brain processed for paraffin embedding or frozen sections.

Modeling Indicators

Electroencephalogram (EEG) recording: Had higher local maximal amplitude and reduced spike frequency compared to the control group.
Histology analysis: Showed Triangulated pyknotic nuclei and cytoplasmic shrinkage in the hippocampal neuron, and induced neuronal loss.

Correlated Product(s): /

Opposite Product(s): Sitagliptin (HY-13749)

Animal Model:	8 weeks, 200-250 g male adult Wistar rats^[1]
Dosage:	5 mg/kg
Administration:	I.p.; hourly at least 3 h until status epilepticus
Result:	Induced seizures in rats.

References

[1] NAREDLA KESAVA REDDY Srivari C. Total Synthesis of (?)-α-Kainic acid via Chirality Transfer through Ireland–Claisen Rearrangement[J]. The Journal of Organic Chemistry, 2013, 78 7: 3355-3360. DOI: 10.1021/jo400001t
[2] EMANUELLE SAGOT. 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]. Journal of Medicinal Chemistry, 2008, 51 14: 4093-4103. DOI: 10.1021/jm800092x
[3] ANNA PASTUSZKO M. E David F Wilson. Effects of Kainic Acid in Rat Brain Synaptosomes: The Involvement of Calcium[J]. Journal of Neurochemistry, 1984, 43 3: 747-754. DOI: 10.1111/j.1471-4159.1984.tb12796.x
[4] N.A SIMONIAN . Kainic acid induces apoptosis in neurons[J]. Neuroscience, 1996, 75 4: Pages 1047-1055. DOI: 10.1016/0306-4522(96)00326-0
[5] CHRISTIAN CHIAMULERA. Domoic Acid Toxicity in Rats and Mice after Intracerebroventricular Administration: Comparison with Excitatory Amino Acid Agonists[J]. Basic & Clinical Pharmacology & Toxicology, 1992, 70 2: 115-120. DOI: 10.1111/j.1600-0773.1992.tb00439.x
[6] QUN WANG. Kainic acid-mediated excitotoxicity as a model for neurodegeneration.[J]. Molecular Neurobiology, 2005, 31 1-3: 3-16. DOI: 10.1385/mn:31:1-3:003
[7] HELENA DOMIN . Neuroprotective potential of mGluR5 antagonist MTEP: effects on kainate-induced excitotoxicity in the rat hippocampus[J]. Pharmacological Reports, 2010, 62 6: Pages 1051-1061. DOI: 10.1016/s1734-1140(10)70367-4

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE manufacturers

Career Henan Chemical Co

Product: KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE 58002-62-3
Price: US $1.00/kg
Min. Order: 1kg
Purity: 95%-99%
Supply Ability: 1000kg
Release date: 2018-12-25

58002-62-3, KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINERelated Search:

KAINIC ACID

2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE

2-CARBOXYL-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE MONOHYDRATE

[2S-(2A,3BETA,4BETA)]-2-CAROXY-4-(1-METHYLETHENYL)-3-PYRROLIDINEACETIC ACID, MONOHYDRATE

(2S,3S,4S)-2-CARBOXY-4-ISOPROPENYL-3-PYRROLIDINEACETIC ACID

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE

(-)-KAINIC ACID, MONOHYDRATE

KAINIC ACID MONOHYDRATE

KAINIC ACID MONOHYDRATE, ISOLATED FROM D

KAINIC ACID HYDRATE

Kainic acid monohydrate,2-Carboxy-3-carboxymethyl-4-isopropenylpyrrolidine

[2S-(2alpha,3beta,4beta)]-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid monohydrate

3-Pyrrolidineaceticacid, 2-carboxy-4-(1-Methylethenyl)-, hydrate (1:1), (2S,3S,4S)-

(2S,3S,4S)-3-(carboxyMethyl)-4-(prop-1-en-2-yl)pyrrolidine-2-carboxylic acid hydrate

([2S-(2a,34]-2-Caroxy-4-(1-methylethenyl)-3-pyrrolidineacetic Acid

kainic acid monohydrate from digenea simplex

(-)-α-Kainic Acid Monohydrate

(?)-(α)-Kainic Acid hydrate

KAINIC ACID 2-CARBOXY-3-CARBOXYMETHYL-4-ISOPROPENYLPYRROLIDINE USP/EP/BP

(-)-(α)-Kainic Acid (hydrate)

(-)-α-Kainic Acid Monohydrate/3-Pyrrolidineaceticacid,2-carboxy-4-(1-methylethenyl)-,hydrate

(-)-Kainic acid monohydrate

(-)-Alpha-Kainic Acid Monohydrate

58002-62-3

C10H15NO4H2O

Cell Signaling and Neuroscience

Cell Biology

BioChemical

Ligand-Gated Ion Channels

Ionotropic Glutamate Receptor Modulators

Ion Channels

Miscellaneous

Glutamate