IBOTENIC ACID

ChemicalBook > CAS DataBase List > IBOTENIC ACID

Product Name: IBOTENIC ACID
CAS No.: 2552-55-8
Chemical Name: IBOTENIC ACID
Synonyms: IBOTENIC ACID;IBOTENIC ACID(RG);DL-Ibotenic acid.;(RS)-Ibotenic acid;(+/-)-IBOTENIC ACID;Ibotenic Acid (CRM);IBOTENIC ACID USP/EP/BP;Ibotenic acid in methanol;Ibotenic Acid [(RS)-Ibotenic acid;Ibotenic acid, excitotoxic agonist
CBNumber: CB0400501
Molecular Formula: C5H6N2O4
Formula Weight: 158.11
MOL File: 2552-55-8.mol

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IBOTENIC ACID Property

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
pka: 2.16±0.10(Predicted)
color: white
Odor: Practically odorless. Faint, meat-like, mild and sweet taste in aqueous dilutions.
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.
InChIKey: IRJCBFDCFXCWGO-UHFFFAOYSA-N
LogP: -1.070 (est)
CAS DataBase Reference: 2552-55-8(CAS DataBase Reference)

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Safety

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
Toxicity: LD50 in mice, rats (mg/kg): 15, 42 i.v.; 38, 129 orally (Theobald)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: I2765
Product name: Ibotenic acid
Purity: ~95%, solid
Packaging: 1mg
Price: $231
Updated: 2024/03/01

Sigma-Aldrich

Product number: I2765
Product name: Ibotenic acid
Purity: ~95%, solid
Packaging: 5mg
Price: $384.6
Updated: 2024/03/01

Sigma-Aldrich

Product number: 5.05024
Product name: Ibotenic Acid - CAS 2552-55-8 - Calbiochem
Packaging: 1MG
Price: $155
Updated: 2024/03/01

Cayman Chemical

Product number: 14584
Product name: Ibotenic Acid
Purity: ≥98%
Packaging: 1mg
Price: $56
Updated: 2024/03/01

Cayman Chemical

Product number: 14584
Product name: Ibotenic Acid
Purity: ≥98%
Packaging: 5mg
Price: $221
Updated: 2024/03/01

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IBOTENIC ACID Chemical Properties,Usage,Production

Description

Ibotenic 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 Properties

Crystalline solid; forms monohydrate; mp151°C (303.8°F) (anhydrous), 145°C (293°F)(monohydrate); soluble in water and alcohol.

Uses

Ibotenic acid has been used to perform surgery in adult male zebra finches (Taeniopygia guttata) to study reversing reinforcement-induced vocal changes.

Uses

Ibotenic 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.

Uses

Neurobiological tool.

Preparation

Isolated from the Japanese fly mushroom. The acid can be produced synthetically.

Definition

A 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.

Hazard

Neurotoxic; causes motor depression, ataxia, changes in mood, perceptions and feelings.

Health Hazard

Ibotenic 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 Activity

NMDA and metabotropic glutamate receptor agonist.

Biochem/physiol Actions

Non-selective agonist with preference for NMDA glutamate receptors; neurotoxin; neuroexcitatory amino acid originally isolated from Amanita species.

storage

-20°C (desiccate)

Purification Methods

It 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.

References

1) 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

Raw materials

Preparation Products

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View Lastest Price from IBOTENIC ACID manufacturers

ARCTIC EXPORTS INC

Product: IBOTENIC ACID 2552-55-8
Price: US $0.00/kg
Min. Order: 10kg
Purity: 99% purity
Supply Ability: 1000 kg
Release date: 2023-12-13

Henan Fengda Chemical Co., Ltd

Product: IBOTENIC ACID 2552-55-8
Price: US $10.00-2.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-04-28

Zhuozhou Wenxi import and Export Co., Ltd

Product: IBOTENIC ACID 2552-55-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-08-11

2552-55-8, IBOTENIC ACIDRelated Search:

4-Phosphonophenylglycine AIDA L-AP4 L-AP3 (+-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID ( AP-3)NMDA ANTAGONIST JNJ 16259685 CPPG (2R,4R)-APDC MPPG IBOTENIC ACID IBOTENIC ACID MONOHYDRATE L-Ibotenic acid (R)-4-BROMO-HOMO-IBOTENIC ACID, >98%,(R)-4-BROMO-HOMO-IBOTENIC ACID (S)-4-BROMO-HOMO-IBOTENIC ACID, >98%,(S)-4-BROMO-HOMO-IBOTENIC ACID (RS)-4-BROMO-HOMO-IBOTENIC ACID TRICHOLOMIC ACID = DIHYDRO-IBOTENIC ACID IBOTENIC ACID UN2811 (III) IBOTENIC ACID(REAGENT / STANDARD GRADE)

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.

IBOTENIC ACID(RG)

5-Isoxazoleaceticacid,-alpha--amino-2,3-dihydro-3-oxo-(9CI)

alpha-Amino-(3-hydroxy-5-isoxazolyl)actetic acid

2-amino-2-(3-ketoisoxazol-5-yl)acetic acid

2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid

2-azanyl-2-(3-oxo-1,2-oxazol-5-yl)ethanoic acid

5-Isoxazoleacetic acid, alpha-aMino-3-hydroxy-

a-AMino-2,3-dihydro-3-oxo-5-isoxazoleacetic Acid

aMino(3-oxo-2,3-dihydro-1,2-oxazol-5-yl)aceticacid

5-Isoxazoleacetic acid,a-aMino-2,3-dihydro-3-oxo-

2-Amino-2-(3-oxo-2,3-dihydroisoxazol-5-yl)acetic acid

Ibotenic Acid - CAS 2552-55-8 - Calbiochem

(RS)-Ibotenic acid

5-Isoxazoleacetic acid, α-amino-2,3-dihydro-3-oxo-

IBOTENIC ACID USP/EP/BP

Ibotenic Acid [(RS)-Ibotenic acid

Ibotenic Acid (CRM)

2-Amino-2-(3-oxo-2,3-dihydro-5-isoxazolyl)acetic Acid

Ibotenic acid in methanol

Ibotenic acid, excitotoxic agonist

Ibotenic acid (mM/ml), excitotoxic agonist

2552-55-8

C5H6ClN2O4

BioChemical

Cell Signaling and Neuroscience

Cell Biology

Ionotropic Glutamate Receptor Modulators

Ion Channels

Ligand-Gated Ion Channels

Glutamate receptor

Glutamate

OXAZOLE

Plant Oils, Toxins, Phenolic Acids & Derivatives