Ibotenic acid

chembox new
ImageFile = ibotenic_acid2.png ImageFile2 = Ibotenic_3d.gif
ImageSize = 200
IUPACName = ("S")-2-amino-2- (3-hydroxyisoxazol-5-yl) acetic acid
OtherNames = Ibotenic acid
Section1 = Chembox Identifiers
Abbreviations =
CASNo = 2552-55-8
EINECS =
PubChem =
ChemSpiderID = 1196
SMILES = N [C@H] (C(O)=O)c1onc(O)c1
InChI =
RTECS =
ChEBI =
KEGG =
Section2 = Chembox Properties
Formula = C₅H₆N₂O₄
MolarMass = 158.11 g/mol
Appearance =drugbox
Density =
MeltingPt = 151-152° (anhydrous); 144-146° (monohydrate)
BoilingPt =
Solubility =
SolubleOther = Soluble
Solvent = Methanol
pKa =
pKb =
IsoelectricPt =
SpecRotation =
RefractIndex =
Viscosity =
Dipole =
Section5 = Chembox Pharmacology
ATCCode =
Bioavail =
Metabolism =
HalfLife =
Excretion =
PregCat =
AdminRoutes =
Section7 = Chembox Hazards
EUClass =
MainHazards =
NFPA-H =
NFPA-F =
NFPA-R =
NFPA-O =
RPhrases =
SPhrases =
RSPhrases =
FlashPt =
Autoignition =
ExploLimits =
PEL =
Section9 = Chembox Related
OtherAnions =
OtherCations =
OtherFunctn =
Function =
OtherCpds =

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." [ [http://www.erowid.org/plants/amanitas/amanitas_info6.shtml Erowid -- Amanitas] ]

Psychopharmacology

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. [Chilton 1975; Theobald et al. 1968] Peak intoxication is reached approximately 2-3 hours after oral ingestion, [Chilton 1975] 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. [Chilton 1975; Ott 1976a]

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. [ [http://www.erowid.org/plants/amanitas/amanitas_info6.shtml Erowid Psychoactive Amanitas Vault : Pharmacology of Amanita Muscaria ] ]

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. [ [http://www.erowid.org/plants/amanitas/amanitas_traditional.shtml Erowid Psychoactive Amanitas Vault : Traditional Uses ] ]

ee also

* "Amanita muscaria"
* Muscimol
* Muscazone

References