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Ibotenic acid

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Ibotenic acid
Names
IUPAC name
(S)-2-amino-2- (3-hydroxyisoxazol-5-yl) acetic acid
Other names
Ibotenic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.151.170 Edit this at Wikidata
  • InChI=1S/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10) checkY
    Key: IRJCBFDCFXCWGO-UHFFFAOYSA-N checkY
  • Key: IRJCBFDCFXCWGO-UHFFFAOYAQ
  • O=C1/C=C(\ON1)C(C(=O)O)N
Properties
C5H6N2O4
Molar mass 158.11 g/mol
Melting point 151-152° (anhydrous); 144-146° (monohydrate)
Solubility in Methanol Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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 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]

In 1960s, ibotenic acid was originally isolated from Amanita ibotengutake in Japan. A. ibotengutake is very like to A. pantherina.

Psychopharmacology

Amanita muscaria, which contains ibotenic acid

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]

Use in Research

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]

Role in shamanic rituals

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]

See also

References

  1. ^ http://www.ncbi.nlm.nih.gov/pubmed/10435405
  2. ^ http://www.nature.com/nature/journal/v311/n5985/abs/311458a0.html
  3. ^ Erowid -- Amanitas
  4. ^ Chilton 1975; Theobald et al. 1968
  5. ^ Chilton 1975
  6. ^ Chilton 1975; Ott 1976a
  7. ^ Erowid Psychoactive Amanitas Vault : Pharmacology of Amanita Muscaria
  8. ^ Erowid Psychoactive Amanitas Vault : Traditional Uses
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