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IBOTENIC ACID

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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
Product Categories:
  • Glutamate receptor
  • Glutamate
  • OXAZOLE
  • Plant Oils, Toxins, Phenolic Acids & Derivatives
Mol File:
2552-55-8.mol
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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)
pka
2.16±0.10(Predicted)
form 
White solid
color 
white
InChIKey
IRJCBFDCFXCWGO-UHFFFAOYSA-N
CAS DataBase Reference
2552-55-8(CAS DataBase Reference)
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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
Toxicity
LD50 in mice, rats (mg/kg): 15, 42 i.v.; 38, 129 orally (Theobald)

MSDS

  • Language:English Provider:ACROS
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IBOTENIC ACID Usage And Synthesis

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.

Uses

Neurobiological tool.

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.

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 ACIDSupplier

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