Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C5H6N2O4 |
| Molecular Weight | 158.1121 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(C(O)=O)C1=CC(=O)NO1
InChI
InChIKey=IRJCBFDCFXCWGO-UHFFFAOYSA-N
InChI=1S/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10)
| Molecular Formula | C5H6N2O4 |
| Molecular Weight | 158.1121 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Ibotenic acid is an isoxazole originally isolated from Amanita mushrooms. The toxic fungi Amanita muscaria, commonly known as the fly agaric, was used to prepare the soma. The feelings of euphoria or invincibility experienced by those who drank it were eventually attributed to a group of isoxazoles centuries later. Two of these - ibotenic acid and muscimol - were first isolated from the Japanese mushroom Amanita ibotengutake in the 1960s, but found in abundance in all Amanita mushrooms. Ibotenic acid is a non-protein amino acid that is unstable and easily decarboxylated to muscimol. Ibotenic acid is a glutamate agonist, acting at glutamate receptors. Ibotenic acid is neurotoxic and used to induce cerebral lesioning in animal models.
CNS Activity
Originator
Curator's Comment: Isolation of ibotenic acid from A. muscaria was reported almost simultaneously from the laboratories of Takemoto and Bowden. reference retrieved from https://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1970-01-01_4_page005.html | https://erowid.org/plants/amanitas/amanitas_info_ott.shtml
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Dopamine dependent behaviours in rats with bilateral ibotenic acid-induced lesions of the globus pallidus. | 1986 Jan |
|
| A pharmacological characterization of the mGluR1 alpha subtype of the metabotropic glutamate receptor expressed in a cloned baby hamster kidney cell line. | 1993 Aug 13 |
|
| Delayed effects of neonatal hippocampal damage on haloperidol-induced catalepsy and apomorphine-induced stereotypic behaviors in the rat. | 1993 Oct 15 |
|
| Gonadectomy does not prevent novelty or drug-induced motor hyperresponsiveness in rats with neonatal hippocampal damage. | 1994 Apr 15 |
|
| RJR-2403: a nicotinic agonist with CNS selectivity II. In vivo characterization. | 1996 Dec |
|
| Effect of Trasina, an ayurvedic herbal formulation, on experimental models of Alzheimer's disease and central cholinergic markers in rats. | 1997 Winter |
|
| Characterization of [(3)H]Quisqualate binding to recombinant rat metabotropic glutamate 1a and 5a receptors and to rat and human brain sections. | 2000 Dec |
|
| Reduced N-acetylaspartate in prefrontal cortex of adult rats with neonatal hippocampal damage. | 2002 Sep |
|
| Neonatal ventral hippocampus lesion leads to reductions in nerve growth factor inducible-B mRNA in the prefrontal cortex and increased amphetamine response in the nucleus accumbens and dorsal striatum. | 2003 |
|
| Effects of T-82, a novel acetylcholinesterase inhibitor, on impaired learning and memory in passive avoidance task in rats. | 2003 Mar 28 |
Patents
Sample Use Guides
Ibotenic acid evokes entheogenic effects in human beings at doses ranging from 50 - 100 mg (Chilton 1975; Theobald et al. 1968).
Ibotenic acid is neurotoxic and used to induce cerebral lesioning in animal models: e.g. rats were bilaterally insular cortex lesioned with ibotenic acid (200-300 nl.; 15 mg/ml).
Route of Administration:
Other
| Substance Class |
Chemical
Created
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admin
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Sat Dec 16 11:21:36 UTC 2023
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| Record UNII |
44AS82FRSI
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Validated (UNII)
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m6186
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1233
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44AS82FRSI
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Ibotenic acid
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204850
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| Related Record | Type | Details | ||
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TARGET -> AGONIST |
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