IBOTENIC ACID

IBOTENIC ACID Basic information
Product Name:IBOTENIC ACID
Synonyms:ALPHA-AMINO-3-HYDROXY-5-ISOOXAZOLACETIC ACID;(+/-)ALPHA-AMINO-3-HYDROXY-5-ISOXAZOLEACETIC ACID;ALPHA-AMINO-3-HYDROXY-5-ISOXAZOLEACETIC ACID;ALPHA-AMINO-(3-HYDROXY-5-ISOXAZOLYL)ACETIC ACID;(+/-)-IBOTENIC ACID;IBOTENIC ACID;α-amino-3-hydroxy-5-isoxazoleacetic acid;DL-Ibotenic acid.
CAS:2552-55-8
MF:C5H6N2O4
MW:158.11
EINECS:
Product Categories:Glutamate receptor;Glutamate;OXAZOLE;Plant Oils, Toxins, Phenolic Acids & Derivatives
Mol File:2552-55-8.mol
IBOTENIC ACID Structure
IBOTENIC ACID Chemical Properties
Melting point 141-147 °C
density 1.621±0.06 g/cm3 (20 ºC 760 Torr)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility H2O: soluble1mg/mL, clear, colorless (with sonication)
form White solid
pka2.16±0.10(Predicted)
color white
Water Solubility Soluble to 10 mM in water and to 100 mM in 1.1eq. NaOH
Stability:Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 month.
InChIKeyIRJCBFDCFXCWGO-UHFFFAOYSA-N
LogP-1.070 (est)
CAS DataBase Reference2552-55-8(CAS DataBase Reference)
Safety Information
Hazard Codes T,Xn
Risk Statements 23/24/25-25-40
Safety Statements 45-38-36/37/39-28A-22-36
RIDADR 1544
WGK Germany 3
RTECS NY2100000
HazardClass 6.1(b)
PackingGroup III
ToxicityLD50 in mice, rats (mg/kg): 15, 42 i.v.; 38, 129 orally (Theobald)
MSDS Information
ProviderLanguage
ACROS English
IBOTENIC ACID Usage And Synthesis
DescriptionIbotenic acid (60573-88-8) is a conformationally restricted analog of glutamate which occurs naturally in Amanita mascaria and related mushrooms.? It is a non-specific glutamate receptor (both NMDA and mGluR) agonist.1 May be used to induce hippocampal lesioning in rat neurodegeneration models.2,3 Induces lesions in the subiculum in a mouse model of Alzheimer’s disease.4
Chemical PropertiesCrystalline solid; forms monohydrate; mp151°C (303.8°F) (anhydrous), 145°C (293°F)(monohydrate); soluble in water and alcohol.
UsesNeurobiological tool.
UsesIbotenic acid is a neuroexcitatory amino acid originally isolated from Amanita species that functions as a NMDA and metabotropic glutamate receptor agonist. As a neurotoxin, ibotenic acid is often used to induce brain lesions in animals that model cognitive dysfunctions resulting from neurodegenerative diseases, traumatic brain injury, and stroke.
UsesIbotenic acid has been used to perform surgery in adult male zebra finches (Taeniopygia guttata) to study reversing reinforcement-induced vocal changes.
DefinitionA isoxazole which, together with muscimol, is largely responsible for the toxicities of a number of mushrooms including those of the genus Amanita. It is a potent excitatory amino acid.
HazardNeurotoxic; causes motor depression, ataxia, changes in mood, perceptions and feelings.
Health HazardIbotenic acid is a potent neurologic aminoacid. It exhibits neuroexcitatory activity andcauses sedative actions on spinal neurons.High doses can cause sleep, hallucinations,distorted perceptions, and nausea. In humansthe symptoms above may be manifested fromingestion of 6–8 mg of ibotenic acid.
LD50 value, oral (mice): 38 mg/kg
LD50 value, intraperitoneal (mice): 15 mg/kg.

Biological ActivityNMDA and metabotropic glutamate receptor agonist.
Biochem/physiol ActionsNon-selective agonist with preference for NMDA glutamate receptors; neurotoxin; neuroexcitatory amino acid originally isolated from Amanita species.
storage-20°C (desiccate)
Purification MethodsIt has been converted to the ammonium salt (m 121-123o dec) dissolved in H2O, passed through an Amberlite IR 120 resin (H+ form) and eluted with H2O. The acidic fractions are collected, evaporated to dryness and the residue recrystallises from H2O as the monohydrate (m 144-146o). The anhydrous acid is obtained by making a slurry with MeOH, decanting and evaporating to dryness, and repeating the process twice more to give the anhydrous acid (m 151-152o). Recrystallisation from H2O gives the monohydrate. [Nakamura Chem Pharm Bull Jpn 19 46 1971.] The ethyl ester forms needles when crystallised from a small volume of Et2O and has m 78-79o and IR (CHCl3) with max 35002300 (OH), 1742 (ester C=O), 1628, 1528cm-1, and UV with λmax (EtOH) at 206nm (ε 7,080). The hydrazide has m 174-175o (from MeOH) with IR (KBr) 1656 (C=O)cm-1.
References1) Nakanishi (1992), Molecular diversity of glutamate receptors and implications for brain function; Science 258 597 2) Jarrard (1989), On the use of ibotenic acid to lesion selectively different components of the hippocampal formation; J. Neurosci. Methods 29 251 3) Isacson and Peschanski (1992), Is there capacity for anatomical and functional repair in the adult somatosensory thalamus?; Exp. Neurol. 115 173 4) George et al. (2014), Lesion of the subiculum reduces the spread of amyloid beta pathology to interconnected brain regions in a mouse model of Alzheimer’s disease; Acta Neuropathol. Commun. 2 17
IBOTENIC ACID Preparation Products And Raw materials
Preparation Productsalpha-amino-2,3-dihydro-2-oxooxazole-5-acetic acid
L-AP4 AIDA 4-Phosphonophenylglycine MPPG (+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST L-AP3 (2R,4R)-APDC JNJ 16259685 CPPG IBOTENIC ACID IBOTENIC ACID MONOHYDRATE (S)-4-BROMO-HOMO-IBOTENIC ACID, >98%,(S)-4-BROMO-HOMO-IBOTENIC ACID L-Ibotenic acid TRICHOLOMIC ACID = DIHYDRO-IBOTENIC ACID IBOTENIC ACID(REAGENT / STANDARD GRADE) (R)-4-BROMO-HOMO-IBOTENIC ACID, >98%,(R)-4-BROMO-HOMO-IBOTENIC ACID IBOTENIC ACID UN2811 (III) (RS)-4-BROMO-HOMO-IBOTENIC ACID

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