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

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 2678
Glutamate receptor ionotropic AMPA 41 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 2678
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 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Dopamine dependent behaviours in rats with bilateral ibotenic acid-induced lesions of the globus pallidus.	1986 Jan	3513907
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	7690672
Delayed effects of neonatal hippocampal damage on haloperidol-induced catalepsy and apomorphine-induced stereotypic behaviors in the rat.	1993 Oct 15	7903225
Gonadectomy does not prevent novelty or drug-induced motor hyperresponsiveness in rats with neonatal hippocampal damage.	1994 Apr 15	8026079
RJR-2403: a nicotinic agonist with CNS selectivity II. In vivo characterization.	1996 Dec	8968367
Reduced N-acetylaspartate in prefrontal cortex of adult rats with neonatal hippocampal damage.	2002 Sep	12183397
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
Effects of T-82, a novel acetylcholinesterase inhibitor, on impaired learning and memory in passive avoidance task in rats.	2003 Mar 28	12650838

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).

Name

Type

Language

IBOTENIC ACID

Common Name

English

DL-IBOTENIC ACID

Common Name

English

IBOTENIC ACID [MI]

Common Name

English

NSC-204850

Code

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