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Names | |
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IUPAC name
(S)-2-Amino-2-(3-hydroxyisoxazol-5-yl)acetic acid
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Other names
Ibotenic acid
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL |
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ChemSpider | |
ECHA InfoCard | 100.151.170 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C5H6N2O4 | |
Molar mass | 158.113 g·mol−1 |
Melting point | 151-152 °C (anhydrous) 144-146 °C (monohydrate) |
H2O: 1 mg/mL 0.1 M NaOH: 10.7 mg/mL 0.1 M HCl: 4.7 mg/mL | |
Hazards | |
GHS labelling:[1] | |
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Danger | |
H301 | |
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).
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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]
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