Ibotenic acid

Ibotenic acid
Names
	IUPAC name (S)-2-Amino-2-(3-hydroxyisoxazol-5-yl)acetic acid
	Other names Ibotenic acid
Identifiers
CAS Number	2552-55-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5854;
ChEMBL	ChEMBL284895 ; (S)-: ChEMBL30285 ;
ChemSpider	1196 ; (S)-: 5036193;
ECHA InfoCard	100.151.170
EC Number	622-405-7;
IUPHAR/BPS	1371;
KEGG	C10600 ;
PubChem CID	1233;
UNII	44AS82FRSI ;
CompTox Dashboard (EPA)	DTXSID40893771 ;
	InChI InChI=1S/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10) Key: IRJCBFDCFXCWGO-UHFFFAOYSA-N ; InChI=1/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10) Key: IRJCBFDCFXCWGO-UHFFFAOYAQ; (S)-: Key: IRJCBFDCFXCWGO-BYPYZUCNSA-N;
	SMILES O=C1/C=C(\ON1)C(C(=O)O)N;
Properties
Chemical formula	C5H6N2O4
Molar mass	158.113 g·mol−1
Melting point	151-152 °C (anhydrous); 144-146 °C (monohydrate)
Solubility in water	H2O: 1 mg/mL; 0.1 M NaOH: 10.7 mg/mL; 0.1 M HCl: 4.7 mg/mL
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301
Precautionary statements	P264, P270, P301+P316, P321, P330, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ibotenic acid or (S)-2-amino-2-(3-hydroxyisoxazol-5-yl)acetic acid, also referred to as ibotenate, is a naturally occurring alpha-amino acid found in certain Amanita mushrooms, that primarily acts as a potent glutamate receptor agonist that precipitates neurological effects and is used experimentally as a brain-lesioning agent in mice and rats.

Ibotenic acid is a conformationally-restricted analogue of glutamate that acts as a non-selective glutamate receptor agonist, strongly activating NMDA, group I and II metabotropic glutamate receptors, and weakly activating AMPA and kainate receptors. It is a prodrug of muscimol, broken down by the liver into this more stable compound, which acts as a potent GABA_A and GABA_A-ρ receptor agonist. Although its psychoactive effects are not well understood, some researchers speculate that ibotenic acid itself may have stimulant properties. Ibotenic acid is biosynthesized from glutamic acid by hydroxylation catalyzed by an Fe(II)/2-oxoglutarate-dependent oxygenase, with subsequent conversion steps carried out by enzymes encoded within a linked biosynthetic gene cluster.

Ibotenic acid is commonly used in research to create site-specific hippocampal brain lesions in rats, allowing for task relearning due to its interaction with glutamate receptors, and is favored over other agents for its selectivity and long-term stability in saline solution. It induces excitotoxicity in mice and rats by overactivating NMDA and metabotropic glutamate receptors, leading to calcium overload and oxidative damage.

In contrast, it targets glutamate-gated chloride channels in invertebrates, causing increased chloride permeability without affecting their excitatory glutamate receptors.