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I2765

Sigma-Aldrich

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
MDL number:
MFCD00069294
UNSPSC Code:
12352209
PubChem Substance ID:
24277994
NACRES:
NA.32

product name

Ibotenic acid, ~95%, solid

Assay

~95%

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

Biochem/physiol Actions

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

Caution

Hygroscopic

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Su-Rong Yang et al.
PLoS biology, 16(4), e2002909-e2002909 (2018-04-14)
The rostromedial tegmental nucleus (RMTg), also called the GABAergic tail of the ventral tegmental area, projects to the midbrain dopaminergic system, dorsal raphe nucleus, locus coeruleus, and other regions. Whether the RMTg is involved in sleep-wake regulation is unknown. In
Intrahippocampal administration of ibotenic acid induced cholinergic dysfunction via NR2A/NR2B expression: Implications of resveratrol against Alzheimer disease pathophysiology
Karthick C, et al.
Frontiers in Molecular Neuroscience, 9, 28-28 (2016)
Loïc J Chareyron et al.
Brain structure & function, 222(9), 3899-3914 (2017-05-11)
Hippocampal damage in adult humans impairs episodic and semantic memory, whereas hippocampal damage early in life impairs episodic memory but leaves semantic learning relatively preserved. We have previously shown a similar behavioral dissociation in nonhuman primates. Hippocampal lesion in adult
Ludivine Pidoux et al.
eLife, 7 (2018-07-26)
Speech is a complex sensorimotor skill, and vocal learning involves both the basal ganglia and the cerebellum. These subcortical structures interact indirectly through their respective loops with thalamo-cortical and brainstem networks, and directly via subcortical pathways, but the role of
Samuel A Neymotin et al.
Journal of neuroscience methods, 275, 1-9 (2016-10-18)
Correlated neuronal activity in the brain is hypothesized to contribute to information representation, and is important for gauging brain dynamics in health and disease. Due to high dimensional neural datasets, it is difficult to study temporal variations in correlation structure.
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