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Merck

I2765

Ibotenic acid

~95% (TLC), solid, neurotoxin

Synonym(s):

α-Amino-3-hydroxy-5-isoxazoleacetic acid

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About This Item

Empirical Formula (Hill Notation):
C5H6N2O4
CAS Number:
2552-55-8
Molecular Weight:
158.11
UNSPSC Code:
12352209
PubChem Substance ID:
24277994
NACRES:
NA.32
MDL number:
MFCD00069294
Assay:
~95%
Form:
solid
Quality level:
100

Key Documents

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Product Name

Ibotenic acid, ~95%, solid

assay

~95%

Quality Level

100

form

solid

color

white

solubility

H2O: 1 mg/mL, clear, colorless (with sonication), 0.1 M NaOH: 10.7 mg/mL, 0.1 M HCl: 4.7 mg/mL

SMILES string

NC(C(O)=O)C1=CC(=O)NO1

InChI

1S/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10)

InChI key

IRJCBFDCFXCWGO-UHFFFAOYSA-N

Gene Information

rat ... Grm1(24414), Grm2(24415)

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Application

Ibotenic acid has been used to perform surgery in adult male zebra finches (Taeniopygia guttata) to study reversing reinforcement-induced vocal changes.
Ibotenic acid has been used as a neurontoxin in rats. It has also been used in inducing a primary permanent lesion monkey cortex M1 neurons.

Biochem/physiol Actions

Non-selective agonist with preference for NMDA glutamate receptors; neurotoxin.
Non-selective agonist with preference for NMDA glutamate receptors; neurotoxin; neuroexcitatory amino acid originally isolated from Amanita species.
Ibotenic acid is an analog of glutamate. It is involved in the excitation of cell bodies and destroys the thalamic reticular nucleus (NRT). It induces high calcium influx leading to neuronal injury. Ibotenic acid is used to induce neurodegeneration due to its excitotoxic functionality.

Disclaimer

Hygroscopic

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000532962
0000532962
0000496904
0000496913
0000496904

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Megan E Fox et al.
ACS chemical neuroscience, 7(12), 1681-1689 (2016-09-13)
Central norepinephrine signaling influences a wide range of behavioral and physiological processes, and the ventral bed nucleus of the stria terminalis (vBNST) receives some of the densest norepinephrine innervation in the brain. Previous work describes norepinephrine neurons as projecting primarily
Angela M Kaindl et al.
Annals of neurology, 72(4), 536-549 (2012-10-31)
Activated microglia play a central role in the inflammatory and excitotoxic component of various acute and chronic neurological disorders. However, the mechanisms leading to their activation in the latter context are poorly understood, particularly the involvement of N-methyl-D-aspartate receptors (NMDARs)
Effects of bilateral microinjections of ibotenic acid in the thalamic reticular nucleus on delta oscillations and sleep in freely-moving rats
Marini G, et al.
Journal of Sleep Research, 9(4), 359-366 (2000)
Anja T Zai et al.
Nature communications, 11(1), 5940-5940 (2020-11-25)
Sensory substitution is a promising therapeutic approach for replacing a missing or diseased sensory organ by translating inaccessible information into another sensory modality. However, many substitution systems are not well accepted by subjects. To explore the effect of sensory substitution
Benjamin M Basile et al.
PLoS biology, 18(6), e3000677-e3000677 (2020-06-13)
A key feature of most social relationships is that we like seeing good things happen to others. Research has implicated the anterior cingulate cortex (ACC) in attaching value to social outcomes. For example, single neurons in macaque ACC selectively code
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