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Ibotenic acid
From Wikipedia, the free encyclopedia
| Ibotenic acid | |
|---|---|
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| IUPAC name | α-Amino-2,3-dihydro-2-oxo-5-oxazoleacetic acid |
| Other names | Ibotenic acid |
| Identifiers | |
| CAS number | [] |
| SMILES | NC(C(=O)O)c1cc(=O)[nH]o1 |
| Properties | |
| Molecular formula | C5H6N2O4 |
| Molar mass | 158.11 g/mol |
| Melting point |
151-152° (anhydrous); 144-146° (monohydrate) |
| Solubility in Methanol | Soluble |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Ibotenic acid is a chemical compound that is naturally occurring in the mushrooms Amanita muscaria and Amanita pantherina, among others. Ibotenic acid is a potent neurotoxin that is used as a brain lesioning agent and has shown to be highly neurotoxic when injected directly into the brains of mice.[1]
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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 50-100mg.[2] Peak intoxication is reached approximately 2-3 hours after oral ingestion,[3] 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.[4]
Ibotenic acid is used as a brain lesioning agent in the medical environment. When injected intracranially, ibotenic acid causes the development of lesions of the brain.[5]
The 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, of sorts. Muscimol is excreted in the urine, and there are stories of shamans "reusing" urine for intoxication purposes.[6]