I2765

Sigma-Aldrich

Ibotenic acid

~95%, solid

Synonym(s):
α-Amino-3-hydroxy-5-isoxazoleacetic acid
Empirical Formula (Hill Notation):
C5H6N2O4
CAS Number:
Molecular Weight:
158.11
MDL number:
PubChem Substance ID:
NACRES:
NA.32
Pricing and availability is not currently available.

Quality Level

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 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.

Packaging

1, 5, 10, 25 mg in glass bottle

Biochem/physiol Actions

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.

Caution

Hygroscopic

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3462 6.1 / PGIII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Jiachao Wang et al.
Behavioural brain research, 372, 112037-112037 (2019-06-17)
Our internal models of the world help us to process information rapidly: in general model-based learning is more rapid than model-free learning. However, the cognitive flexibility required to overcome cognitive predispositions can let us down: it is not fully developed...
null
Homare Yamahachi et al.
PloS one, 15(8), e0236333-e0236333 (2020-08-11)
Research on the songbird zebra finch (Taeniopygia guttata) has advanced our behavioral, hormonal, neuronal, and genetic understanding of vocal learning. However, little is known about the impact of typical experimental manipulations on the welfare of these birds. Here we explore...
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)
L T Lopes et al.
Acta physiologica (Oxford, England), 211(3), 528-537 (2014-03-13)
Although periaqueductal grey matter activation is known to elicit respiratory and cardiovascular responses, the role of this midbrain area in the compensatory responses to hypoxia is still unknown. To test the participation of the periaqueductal grey matter in cardiorespiratory and...

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