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IBOTENIC ACID

IBOTENIC ACID Structure
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 [(RS)-Ibotenic acid;α-amino-3-hydroxy-5-isoxazoleacetic acid;2-amino-2-(3-ketoisoxazol-5-yl)acetic acid
CBNumber:
CB0400501
Molecular Formula:
C5H6N2O4
Molecular Weight:
158.11
MOL File:
2552-55-8.mol
MSDS File:
SDS
Modify Date:
2024/6/26 9:58:26

IBOTENIC ACID 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
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)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P405-P501
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)
NFPA 704
3
2 0

IBOTENIC ACID price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) I2765 Ibotenic acid ~95%, solid 2552-55-8 1MG ₹21880 2022-06-14 Buy
Sigma-Aldrich(India) I2765 Ibotenic acid ~95%, solid 2552-55-8 5MG ₹65350 2022-06-14 Buy
Sigma-Aldrich(India) I2765 Ibotenic acid ~95%, solid 2552-55-8 10MG ₹123750 2022-06-14 Buy
Sigma-Aldrich(India) I2765 Ibotenic acid ~95%, solid 2552-55-8 25MG ₹236030 2022-06-14 Buy
Sigma-Aldrich(India) 5.05024 Ibotenic Acid - CAS 2552-55-8 - Calbiochem 2552-55-8 1MG ₹14100 2022-06-14 Buy
Product number Packaging Price Buy
I2765 1MG ₹21880 Buy
I2765 5MG ₹65350 Buy
I2765 10MG ₹123750 Buy
I2765 25MG ₹236030 Buy
5.05024 1MG ₹14100 Buy

IBOTENIC ACID Chemical Properties,Uses,Production

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 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.

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.

Preparation

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

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.

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.

IBOTENIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 166)Suppliers
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IBOTENIC ACID Spectrum

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 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