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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 of IBOTENIC ACID

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 ( + / - )

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.

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

PubMed

TitleDatePubMed
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
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
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
  • Download
Name Type Language
NSC-204850
Preferred Name English
IBOTENIC ACID
MI  
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
Created by admin on Tue Apr 01 16:22:02 GMT 2025 , Edited by admin on Tue Apr 01 16:22:02 GMT 2025
PRIMARY Merck Index
PUBCHEM
1233
Created by admin on Tue Apr 01 16:22:02 GMT 2025 , Edited by admin on Tue Apr 01 16:22:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID40893771
Created by admin on Tue Apr 01 16:22:02 GMT 2025 , Edited by admin on Tue Apr 01 16:22:02 GMT 2025
PRIMARY
CAS
2552-55-8
Created by admin on Tue Apr 01 16:22:02 GMT 2025 , Edited by admin on Tue Apr 01 16:22:02 GMT 2025
PRIMARY
FDA UNII
44AS82FRSI
Created by admin on Tue Apr 01 16:22:02 GMT 2025 , Edited by admin on Tue Apr 01 16:22:02 GMT 2025
PRIMARY
WIKIPEDIA
Ibotenic acid
Created by admin on Tue Apr 01 16:22:02 GMT 2025 , Edited by admin on Tue Apr 01 16:22:02 GMT 2025
PRIMARY
NSC
204850
Created by admin on Tue Apr 01 16:22:02 GMT 2025 , Edited by admin on Tue Apr 01 16:22:02 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST