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
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
excitory amino acid, neurotoxin, neurobiology tool
The Uses of KAINIC ACID
Neurobiological tool.
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
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) |
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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