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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5854
ChEMBL	ChEMBL284895 Y (S)-: ChEMBL30285 Y
ChemSpider	1196 Y (S)-: 5036193
ECHA InfoCard	100.151.170
EC Number	622-405-7
IUPHAR/BPS	1371
KEGG	C10600 Y
PubChem CID	1233
UNII	44AS82FRSI Y
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) Y Key: IRJCBFDCFXCWGO-UHFFFAOYSA-N Y 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:[1]
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). N verify (what is YN ?) Infobox references

Ibotenic acid or (S)-2-amino-2-(3-hydroxyisoxazol-5-yl)acetic acid, also referred to as ibotenate, is a chemical compound and psychoactive drug which occurs naturally in Amanita muscaria and related species of mushrooms typically found in the temperate and boreal regions of the northern hemisphere. It is a prodrug of muscimol, broken down by the liver to that much more stable compound.^[2] It is a conformationally-restricted analogue of the neurotransmitter glutamate, and due to its structural similarity to this neurotransmitter, acts as a non-selective glutamate receptor agonist.^[3] Because of this, ibotenic acid can be a powerful neurotoxin in high doses, and is employed as a "brain-lesioning agent" through cranial injections in scientific research.^[4][5] The neurotoxic effects appear to be dose-related and risks are unclear through consumption of ibotenic-acid containing fungi, although thought to be negligible in small doses.^{[6][better source needed]}