Ibotenic acid

From Wikipedia, the free encyclopedia
  (Redirected from Ibotenic Acid)
Jump to: navigation, search
Ibotenic acid
Ibotenic acid2.png
Ibotenic acid 3D structure.png
Identifiers
CAS number 2552-55-8 N
PubChem 1233
ChemSpider 1196 YesY
ChEMBL CHEMBL284895 YesY, CHEMBL30285
IUPHAR ligand 1371
Jmol-3D images Image 1
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 (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Ibotenic acid (ibotenate) is a chemical compound that occurs naturally in Amanita muscaria and related species of mushrooms. Due to its similarity to the neurotransmitter glutamic acid, 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]

Psychopharmacology[edit]

Amanita muscaria, which contains ibotenic acid

Unlike muscimol, the principal psychoactive constituent of Amanita muscaria, which is understood to cause sedation and dissociation, ibotenic acid's psychoactive effects are not known independent of its serving as a prodrug to muscimol.[4][5]

Use in research[edit]

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.[6]

Name[edit]

"Ibotenic" comes from the Japanese name for the Amanita strobiliformis mushroom, iboten(gutake), from which it was first isolated.

See also[edit]

References[edit]

  1. ^ Becker, A; Grecksch, G; Bernstein, HG; Höllt, V; Bogerts, B (1999). "Social behaviour in rats lesioned with ibotenic acid in the hippocampus: quantitative and qualitative analysis". Psychopharmacology 144 (4): 333–8. doi:10.1007/s002130051015. PMID 10435405.  edit
  2. ^ Isacson, O; Brundin, P; Kelly, PA; Gage, FH; Björklund, A (1984). "Functional neuronal replacement by grafted striatal neurones in the ibotenic acid-lesioned rat striatum". Nature 311 (5985): 458–60. Bibcode:1984Natur.311..458I. doi:10.1038/311458a0. PMID 6482962.  edit
  3. ^ Erowid -- Amanitas
  4. ^ Chilton 1975; Theobald et al. 1968
  5. ^ Chilton 1975; Ott 1976a
  6. ^ Erowid Psychoactive Amanitas Vault : Pharmacology of Amanita Muscaria