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

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

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...
The median raphe nucleus lesion attenuates amnesic effects of ketamine on short-term memory in rats
Babar E, et al.
Journal of Islamic Academy of Sciences, 7(4), 241-246 (1994)
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)
Anthony J Gifuni et al.
Neuropharmacology, 63(6), 945-957 (2012-07-31)
Midbrain dopamine neurons play a key role in goal-directed behaviour as well as in some psychiatric disorders. Recent studies have provided electrophysiological, anatomical and biochemical evidence that the lateral habenula (LHb) exerts strong inhibitory control over midbrain dopamine neurons. However...

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