| Ibotenic acid | |
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(S)-2-amino-2-(3-hydroxyisoxazol-5-yl) acetic acid |
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Other names
Ibotenic acid |
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| Identifiers | |
| CAS number | 2552-55-8 |
| PubChem | 1233 |
| ChemSpider | 1196 |
| ChEMBL | CHEMBL284895 |
| IUPHAR ligand | 1371 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C5H6N2O4 |
| Molar mass | 158.11 g/mol |
| Melting point |
151-152° (anhydrous); 144-146° (monohydrate) |
| Solubility in Methanol | Soluble |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Ibotenic acid is a chemical compound that is naturally occurring in the mushrooms Amanita muscaria and Amanita pantherina, among others. Ibotenic acid is a powerful neurotoxin and deliriant that is used as a "brain-lesioning agent"[1][2] and has shown to be highly neurotoxic when injected directly into the brains of mice and rats.[3]
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When ibotenic acid is ingested, a small portion is decarboxylated into muscimol. Ibotenic acid evokes entheogenic effects in human beings at doses in range of 50-100 mg.[4] Peak intoxication is reached approximately 2-3 hours after oral ingestion,[5] consisting of one or all of the following; visual distortions/hallucinations, loss of equilibrium, muscle twitching (commonly mislabeled as convulsions), and altered sensory perception. These effects generally last for 6-8 hours, varying with dose.[6]
Ibotenic acid is used as a brain-lesioning agent in the research environment. When injected intracranially, ibotenic acid causes the development of excitotoxic lesions of the brain. This method of experimental brain lesioning may be preferable in certain circumstances because, while it destroys neuron bodies in a particular area, tracts that cross through the target nucleus are not damaged.[7]
Ibotenic acid (coupled with other substances such as muscimol, found in Amanita muscaria and Amanita pantherina) is a common factor in shamanic rituals, used as a sacrament. Muscimol is excreted unchanged in the urine in relatively large amounts, and there are stories of shamans "reusing" urine for intoxication purposes, or the rest of the tribe making use of the shaman's urine.[8]
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