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HomeProduct name listKAINIC ACID

KAINIC ACID

  • CAS NO.:487-79-6
  • Empirical Formula: C10H15NO4
  • Molecular Weight: 213.23
  • MDL number: MFCD00077806
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-28 13:53:22
KAINIC ACID Structural

What is KAINIC ACID?

Description

Kainic acid (487-79-6) is a conformationally restricted glutamate analog which acts as a selective agonist at kainate receptors. CNS stimulant and neurotoxin. Kainic acid is a classic neuroexcitatory agent for induction of seizures in laboratory animals (typical dose 10-30 mg/kg).

Chemical properties

soluble in 0.1 M NaOH

The Uses of KAINIC ACID

(-)-α-Kainic Acid is a naturally occurring neuroexcitatory chemical that is an selective agonist for a subtype of ionotropic glutamate receptor. Administration of (-)-α-Kainic Acid has been shown to increase production of reactive oxygen species, mitochondrial dysfunction, and apoptosis in neurons in many regions of the brain, particularly in the hippocampal subregions and in the hilus of dentate gyrus.

The Uses of KAINIC ACID

glutamate receptor agonist, anthelmintic

The Uses of KAINIC ACID

excitory amino acid, neurotoxin, neurobiology tool

The Uses of KAINIC ACID

Neurobiological tool.

What are the applications of Application

Kainic acid is an excitatory and excitotoxic glutamate-mimic kainate receptor agonist

Definition

ChEBI: Kainic acid is a dicarboxylic acid, a pyrrolidinecarboxylic acid, a L-proline derivative and a non-proteinogenic L-alpha-amino acid. It has a role as an antinematodal drug and an excitatory amino acid agonist. It is a conjugate acid of a kainate(1-).

Biological Activity

Selective agonist at kainate receptors. Potent excitant and neurotoxin. Also available as part of the Kainate Receptor Tocriset™ .

storage

Room temperature

Purification Methods

Purify the acid by adsorbing on to a strongly acidic ion-exchange resin (Merck), elute the diacid with aqueous M NaOH, the eluate is evaporated, H2O is added, and filtered through a weakly acidic ion-exchange resin (Merck). The filtrate is then evaporated and recrystallised from EtOH. Its solubility is 0.1g in 1mL of 0.5N HCl. (±)--Kainic acid is recrystallised from H2O with m 230-260o. UV (MeOH): 219 (log 3.9); max 1HNMR (CCl4, 100MHz, Me4Si standard) : 1.64 (s 1H), 1.70 (s 3H), 3.24 (d J 7.5, 2H), 3.3-4.2 (1H), 3.70 (s 3H), 3.83 (s 3H), 4.35 (dd J 7.5, J 14.5, 1H), 5.21 (t J 7.5, 1H), 7.26 (t J 7.5, 1H). [Oppolzer & Andres Helv Chim Acta 62 2282 1979, Beilstein 22 III/IV 1523.]

References

1) Watkins et al. (1981), Excitatory amino acid transmitters; Ann. Rev. Pharmacol. Toxicol., 21 165

Properties of KAINIC ACID

Melting point: 253-254 C
Boiling point: 353.22°C (rough estimate)
alpha  D24 -14.8° (c = 1.01)
Density  1.2177 (rough estimate)
refractive index  1.4368 (estimate)
storage temp.  Keep in dark place,Sealed in dry,2-8°C
solubility  H2O: soluble
pka 2.03±0.60(Predicted)
form  White to off-white solid.
color  White
Water Solubility  Soluble to 25 mM in water
Stability: Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
InChI InChI=1S/C10H15NO4/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)/t6-,7+,9-/m0/s1
EPA Substance Registry System 3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethenyl)-, (2S,3S,4S)- (487-79-6)

Safety information for KAINIC ACID

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H312:Acute toxicity,dermal
H332:Acute toxicity,inhalation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P330:Rinse mouth.
P363:Wash contaminated clothing before reuse.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P501:Dispose of contents/container to..…

Computed Descriptors for KAINIC ACID

InChIKey VLSMHEGGTFMBBZ-OOZYFLPDSA-N
SMILES N1C[C@H](C(C)=C)[C@H](CC(O)=O)[C@H]1C(O)=O

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