Basic information
- CAS
2552-55-8- Standard SMILES
NC(C(=O)O)c1cc(=O)[nH]o1- InChIKey
IRJCBFDCFXCWGO-UHFFFAOYSA-N- Molecular formula
- C5H6N2O4
- Average molar mass
- 158.11 g/mol
- Monoisotopic mass
- 158.03275668
Overview
Ibotenic acid is a non-proteinogenic alpha-amino acid. It has a role as a neurotoxin.
Names & identifiers
- Preferred name
- Ibotenic Acid
- IUPAC
- 2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid
- English name
- Ibotenic acid
- Molecular formula
- C5H6N2O4
- Molecular weight
- 158.11
Names & synonyms
Ibotenic acid2552-55-8DL-Ibotenic acid(RS)-Ibotenic acidAcid, Ibotenicalpha-Amino-2,3-dihydro-3-oxo-5-isoxazoleacetic acid2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid2-amino-2-(3-oxoisoxazol-5-yl)acetic acid44AS82FRSI5-Isoxazoleacetic acid, alpha-amino-2,3-dihydro-3-oxo-DTXSID408937714-Isoxazoline-5-acetic acid, alpha-amino-3-oxo-
Show more names
IBOTENIC ACID(RG)DL-Ibotenic acid.Ibotenic Acid (CRM)IBOTENIC ACID USP/EP/BPIbotenic acid in methanolIbotenic Acid [(RS)-Ibotenic acidIbotenic acid, excitotoxic agonist
NSC-2048502-Azaniumyl-2-(3-oxo-1,2-oxazol-5-yl)acetate(+-)-Ibotenic acidRefChem:789640DTXCID701323806637-415-7Ibotenate(+/-)-Ibotenic acid
Database identifiers
- CAS
2552-55-8、60573-88-8
Properties
Computed structural properties
- XLogP
- -3.9
- Topological polar surface area
- 102 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 235
Experimental & physicochemical properties
DrugsDEA NFLIS-Drug Category -> Hallucinogens
Physicochemical properties
- Melting point
- 141 · 141-147 °C
- Density
- 1.621 · 1.621±0.06 g/cm3 (20 ºC 760 Torr)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- 2 O: · H2O: soluble1mg/mL, clear, colorless (with sonication)
- form
- White solid
- pka
- 2.16 · 2.16±0.10(Predicted)
- color
- white
- Odor
- Practically odorless. Faint, meat-like, mild and sweet taste in aqueous dilutions.
- Water Solubility
- 10 mM · Soluble to 10 mM in water and to 100 mM in 1.1eq. NaOH
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 month.
- InChI
- 1S/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
Hazard information
Hazard Classes and Categories
Acute Tox. 3 (100%)
Acute Tox. 3 (100%)
Toxicology
Health EffectsIbotenic acid is neurotoxic. (L1141)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
A portion of ibotenic acid is metabolized to muscimol, a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets. (L1142, L1672)
Signs and Symptoms
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs that bind to and activate excitatory amino acid receptors.
Uses & manufacturing
UsesIbotenic acid is used as a brain lesioning agent in the medical environment. When injected intracranially, ibotenic acid causes the development of lesions of the brain. (L1141)
Applications
DescriptionIbotenic acid (60573-88-8) is a conformationally restricted analog of glutamate which occurs naturally in Amanita mascaria and related mushrooms. It is a non-specific glutamate receptor (both NMDA and mGluR) agonist.1 May be used to induce hippocampal lesioning in rat neurodegeneration models.2,3 Induces lesions in the subiculum in a mouse model of Alzheimer’s disease.4
UsesIbotenic acid has been used to perform surgery in adult male zebra finches (Taeniopygia guttata) to study reversing reinforcement-induced vocal changes.
UsesIbotenic acid is a neuroexcitatory amino acid originally isolated from Amanita species that functions as a NMDA and metabotropic glutamate receptor agonist. As a neurotoxin, ibotenic acid is often used to induce brain lesions in animals that model cognitive dysfunctions resulting from neurodegenerative diseases, traumatic brain injury, and stroke.
UsesNeurobiological tool.
Preparation methods
PreparationIsolated from the Japanese fly mushroom. The acid can be produced synthetically.
Upstream & downstream products
Downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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