2552-55-8 Usage
Description
Ibotenic acid (60573-88-8) is a conformationally restricted analog of glutamate, which occurs naturally in Amanita mascaria and related mushrooms. It is a potent excitatory amino acid and a neuroexcitatory agent that functions as an NMDA and metabotropic glutamate receptor agonist. Ibotenic acid is also a neurotoxin, responsible for the toxicities of several mushrooms, including those of the genus Amanita. It is a crystalline solid, forming a monohydrate, with a melting point of 151°C (303.8°F) for the anhydrous form and 145°C (293°F) for the monohydrate. Ibotenic acid is soluble in water and alcohol.
Uses
1. Used in Neurobiological Research:
Ibotenic acid is used as a neurobiological tool for studying the effects of glutamate receptor agonism on the nervous system. It helps researchers understand the role of glutamate receptors in various neurological processes and disorders.
2. Used in Animal Models for Neurodegenerative Diseases:
Ibotenic acid is used as a neurotoxin to induce brain lesions in animals, which serve as models for cognitive dysfunctions resulting from neurodegenerative diseases, traumatic brain injury, and stroke. This helps researchers study the underlying mechanisms of these conditions and develop potential treatments.
3. Used in Vocalization Studies in Zebra Finches:
Ibotenic acid has been used in surgery on adult male zebra finches (Taeniopygia guttata) to study the reversal of reinforcement-induced vocal changes. This application aids in understanding the neural mechanisms involved in vocal learning and communication in these birds.
4. Used in Alzheimer's Disease Research:
Ibotenic acid induces lesions in the subiculum in a mouse model of Alzheimer's disease, helping researchers investigate the progression of the disease and the potential for therapeutic interventions.
Hazard
Neurotoxic; causes motor depression, ataxia, changes in mood, perceptions and feelings.
Health Hazard
Ibotenic acid is a potent neurologic aminoacid. It exhibits neuroexcitatory activity andcauses sedative actions on spinal neurons.High doses can cause sleep, hallucinations,distorted perceptions, and nausea. In humansthe symptoms above may be manifested fromingestion of 6–8 mg of ibotenic acid.LD50 value, oral (mice): 38 mg/kgLD50 value, intraperitoneal (mice): 15 mg/kg.
Biological Activity
NMDA and metabotropic glutamate receptor agonist.
Biochem/physiol Actions
Non-selective agonist with preference for NMDA glutamate receptors; neurotoxin; neuroexcitatory amino acid originally isolated from Amanita species.
Purification Methods
It has been converted to the ammonium salt (m 121-123o dec) dissolved in H2O, passed through an Amberlite IR 120 resin (H+ form) and eluted with H2O. The acidic fractions are collected, evaporated to dryness and the residue recrystallises from H2O as the monohydrate (m 144-146o). The anhydrous acid is obtained by making a slurry with MeOH, decanting and evaporating to dryness, and repeating the process twice more to give the anhydrous acid (m 151-152o). Recrystallisation from H2O gives the monohydrate. [Nakamura Chem Pharm Bull Jpn 19 46 1971.] The ethyl ester forms needles when crystallised from a small volume of Et2O and has m 78-79o and IR (CHCl3) with
max 35002300 (OH), 1742 (ester C=O), 1628, 1528cm-1, and UV with λmax (EtOH) at 206nm (ε 7,080).
The hydrazide has m 174-175o (from MeOH) with IR (KBr) 1656 (C=O)cm-1.
References
1) Nakanishi (1992), Molecular diversity of glutamate receptors and implications for brain function; Science 258 597
2) Jarrard (1989), On the use of ibotenic acid to lesion selectively different components of the hippocampal formation; J. Neurosci. Methods 29 251
3) Isacson and Peschanski (1992), Is there capacity for anatomical and functional repair in the adult somatosensory thalamus?; Exp. Neurol. 115 173
4) George et al. (2014), Lesion of the subiculum reduces the spread of amyloid beta pathology to interconnected brain regions in a mouse model of Alzheimer’s disease; Acta Neuropathol. Commun. 2 17
Check Digit Verification of cas no
The CAS Registry Mumber 2552-55-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,5 and 2 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2552-55:
(6*2)+(5*5)+(4*5)+(3*2)+(2*5)+(1*5)=78
78 % 10 = 8
So 2552-55-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10)
