Ibotenic acid

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Ibotenic acid
IUPAC name α-Amino-2,3-dihydro-2-oxo
-5-oxazoleacetic acid
Other names Ibotenic acid
Identifiers
CAS number [2552-55-8]
SMILES N[C@H](C(O)=O)c1onc(O)c1
Properties
Molecular formula C5H6N2O4
Molar mass 158.11 g/mol
Appearance drugbox
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

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" and has shown to be highly neurotoxic when "injected directly into the brains of mice and rats."[1]

Contents

[edit] Psychopharmacology

Amanita muscaria which contains ibotenic acid
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.[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]

[edit] Medical uses

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]

[edit] Role in shamanic rituals

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 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.[6]

[edit] See also

[edit] References

  1. ^ Erowid -- Amanitas
  2. ^ Chilton 1975; Theobald et al. 1968
  3. ^ Chilton 1975
  4. ^ Chilton 1975; Ott 1976a
  5. ^ Erowid Psychoactive Amanitas Vault : Pharmacology of Amanita Muscaria
  6. ^ Erowid Psychoactive Amanitas Vault : Traditional Uses