Ibotenic acid

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Ibotenic acid
Ibotenic acid2.png
Ibotenic acid 3D structure.png
Names
IUPAC name
(S)-2-amino-2-(3-hydroxyisoxazol-5-yl) acetic acid
Other names
Ibotenic acid
Identifiers
2552-55-8 N
ChEMBL ChEMBL284895 YesY
ChEMBL30285 YesY
ChemSpider 1196 YesY
IUPHAR ligand 1371
Jmol-3D images Image
PubChem 1233
Properties
C5H6N2O4
Molar mass 158.11 g/mol
Melting point 151-152° (anhydrous); 144-146° (monohydrate)
Solubility in Methanol Soluble
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Ibotenic acid, also referred to as ibotenate, is a chemical compound and psychoactive drug which occurs naturally in Amanita muscaria and related species of mushrooms. It is a conformationally-restricted analogue of the neurotransmitter glutamate, and due to its structural similarity to this neurotransmitter, acts as a non-selective glutamate receptor agonist.[1] Because of this, ibotenic acid is a powerful neurotoxin, and is employed as a "brain-lesioning agent" in scientific research.[2][3]

Pharmacology[edit]

Amanita muscaria, which contains ibotenic acid

Ibotenic acid acts as a potent agonist of the NMDA and group I (mGluR1 and mGluR5) and II (mGluR2 and mGluR3) metabotropic glutamate receptors.[1][4] It is inactive at group III mGluRs.[5] Ibotenic acid also acts as a weak agonist of the AMPA and kainate receptors.[1][4] In addition, due to in vivo decarboxylation into muscimol, it acts indirectly as a potent GABAA and GABAA-ρ receptor agonist.[4]

Unlike muscimol, the principal psychoactive constituent of Amanita muscaria that is understood to cause sedation and dissociation, ibotenic acid's psychoactive effects are not known independent of it serving as a prodrug to muscimol.[6][7]

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.[8]

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. ^ a b c Tommy Liljefors; Povl Krogsgaard-Larsen; Ulf Madsen (25 July 2002). Textbook of Drug Design and Discovery, Third Edition. CRC Press. pp. 263–. ISBN 978-0-415-28288-8. 
  2. ^ 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
  3. ^ 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
  4. ^ a b c Wantanabe (23 July 1999). Pharmacological Research on Traditional Herbal Medicines. CRC Press. pp. 107–. ISBN 978-90-5702-054-4. 
  5. ^ Hermit MB, Greenwood JR, Nielsen B, Bunch L, Jørgensen CG, Vestergaard HT et al. (2004). "Ibotenic acid and thioibotenic acid: a remarkable difference in activity at group III metabotropic glutamate receptors". Eur. J. Pharmacol. 486 (3): 241–50. doi:10.1016/j.ejphar.2003.12.033. PMID 14985045. 
  6. ^ Chilton 1975; Theobald et al. 1968
  7. ^ Chilton 1975; Ott 1976a
  8. ^ Erowid Psychoactive Amanitas Vault : Pharmacology of Amanita Muscaria