IBOTENIC ACID

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

Structure Search

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)

HIDE SMILES / InChI

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	( + / - )

Description
Sources: https://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1970-01-01_4_page005.html | https://eic.rsc.org/feature/the-drink-of-the-gods/2020250.article | https://www.ncbi.nlm.nih.gov/pubmed/24573533 | https://www.ncbi.nlm.nih.gov/pubmed/40808

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Metabotropic glutamate receptor 1 Target ID: CHEMBL2111335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9178659 \| https://www.ncbi.nlm.nih.gov/pubmed/14985045 \| https://www.ncbi.nlm.nih.gov/pubmed/17340770	Agonist 2752
Glutamate receptor ionotropic AMPA 42 Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17340770 \| https://www.ncbi.nlm.nih.gov/pubmed/14985045 \| https://www.ncbi.nlm.nih.gov/pubmed/21067182	Agonist 2752
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24573533 \| https://www.ncbi.nlm.nih.gov/pubmed/14985045 \| https://www.ncbi.nlm.nih.gov/pubmed/17340770	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Effects of T-82, a novel acetylcholinesterase inhibitor, on impaired learning and memory in passive avoidance task in rats.	2003-03-28	12650838
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	14622910
Reduced N-acetylaspartate in prefrontal cortex of adult rats with neonatal hippocampal damage.	2002-09	12183397
Characterization of [(3)H]Quisqualate binding to recombinant rat metabotropic glutamate 1a and 5a receptors and to rat and human brain sections.	2000-12	11080213
Effect of Trasina, an ayurvedic herbal formulation, on experimental models of Alzheimer's disease and central cholinergic markers in rats.	1997	9449054
RJR-2403: a nicotinic agonist with CNS selectivity II. In vivo characterization.	1996-12	8968367
Gonadectomy does not prevent novelty or drug-induced motor hyperresponsiveness in rats with neonatal hippocampal damage.	1994-04-15	8026079
Delayed effects of neonatal hippocampal damage on haloperidol-induced catalepsy and apomorphine-induced stereotypic behaviors in the rat.	1993-10-15	7903225
A pharmacological characterization of the mGluR1 alpha subtype of the metabotropic glutamate receptor expressed in a cloned baby hamster kidney cell line.	1993-08-13	7690672
Dopamine dependent behaviours in rats with bilateral ibotenic acid-induced lesions of the globus pallidus.	1986-01	3513907

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Activation of glutamate release from C6 cells by ibotenic acid was evaluated (EC50 = 10 nM).

Substance Class	Chemical Created by `admin` on `Tue Apr 01 16:22:02 GMT 2025` Edited by `admin` on `Tue Apr 01 16:22:02 GMT 2025`
Record UNII	44AS82FRSI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-204850

Preferred Name

English

IBOTENIC ACID

Common Name

English

DL-IBOTENIC ACID

Common Name

English

IBOTENIC ACID [MI]

Common Name

English

IBOTENIC ACID, (±)-

Common Name

English

Ibotenic acid [WHO-DD]

Common Name

English

(RS)-IBOTENIC ACID

Common Name

English

(±)-IBOTENIC ACID

Common Name

English

5-ISOXAZOLEACETIC ACID, .ALPHA.-AMINO-2,3-DIHYDRO-3-OXO-

Systematic Name

English

Code System Code Type Description

MERCK INDEX

m6186