Synonym
Ibotenic Acid; Ibotenate
IUPAC/Chemical Name
2-Amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid
InChi Key
IRJCBFDCFXCWGO-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10)
SMILES Code
O=C(O)C(N)C(ON1)=CC1=O
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Ibotenic acid has agonist activity at both the N-methyl-D-aspartate (NMDA) and trans-ACPD or metabolotropic quisqualate (Qm) receptor sites.
In vitro activity:
Ibo (ibotenic acid) induced stimulation of phosphoinositide (PI) hydrolysis, on the other hand, is unaffected by either of these treatments. This study therefore concludes that Ibo is capable of acting at both NMDA and trans-ACPD receptors in the CNS, although only activation of NMDA receptors is involved in Ibo neurotoxicity.
Reference: Mol Chem Neuropathol. 1992 Feb-Apr;16(1-2):1-10. https://pubmed.ncbi.nlm.nih.gov/1325800/
In vivo activity:
In Figures 4A,B, results showed that IBO (ibotenic acid)-induced group exhibited significant (P < 0.01) down-regulation of α7-nAChR and up-regulation of m1AChR mRNA levels by p < 0.001 when compared to control groups. In RSV-treated groups, the expression of acetylcholine receptor, α7-nAChR and m1 AChR levels were significantly (P < 0.05) brought back when compared to IBO-induced rat groups.
Reference: Front Mol Neurosci. 2016 Apr 26;9:28. https://pubmed.ncbi.nlm.nih.gov/27199654/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
5.0 |
31.62 |
| Water |
3.3 |
20.81 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
158.11
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Zinkand WC, Moore WC, Thompson C, Salama AI, Patel J. Ibotenic acid mediates neurotoxicity and phosphoinositide hydrolysis by independent receptor mechanisms. Mol Chem Neuropathol. 1992 Feb-Apr;16(1-2):1-10. doi: 10.1007/BF03159956. PMID: 1325800.
2. Karthick C, Periyasamy S, Jayachandran KS, Anusuyadevi M. Intrahippocampal Administration of Ibotenic Acid Induced Cholinergic Dysfunction via NR2A/NR2B Expression: Implications of Resveratrol against Alzheimer Disease Pathophysiology. Front Mol Neurosci. 2016 Apr 26;9:28. doi: 10.3389/fnmol.2016.00028. PMID: 27199654; PMCID: PMC4844917.
3. Marini G, Ceccarelli P, Mancia M. Effects of bilateral microinjections of ibotenic acid in the thalamic reticular nucleus on delta oscillations and sleep in freely-moving rats. J Sleep Res. 2000 Dec;9(4):359-66. doi: 10.1046/j.1365-2869.2000.00224.x. PMID: 11123522.
In vitro protocol:
1. Zinkand WC, Moore WC, Thompson C, Salama AI, Patel J. Ibotenic acid mediates neurotoxicity and phosphoinositide hydrolysis by independent receptor mechanisms. Mol Chem Neuropathol. 1992 Feb-Apr;16(1-2):1-10. doi: 10.1007/BF03159956. PMID: 1325800.
In vivo protocol:
1. Karthick C, Periyasamy S, Jayachandran KS, Anusuyadevi M. Intrahippocampal Administration of Ibotenic Acid Induced Cholinergic Dysfunction via NR2A/NR2B Expression: Implications of Resveratrol against Alzheimer Disease Pathophysiology. Front Mol Neurosci. 2016 Apr 26;9:28. doi: 10.3389/fnmol.2016.00028. PMID: 27199654; PMCID: PMC4844917.
2. Marini G, Ceccarelli P, Mancia M. Effects of bilateral microinjections of ibotenic acid in the thalamic reticular nucleus on delta oscillations and sleep in freely-moving rats. J Sleep Res. 2000 Dec;9(4):359-66. doi: 10.1046/j.1365-2869.2000.00224.x. PMID: 11123522.
1: Stebelska K. Fungal hallucinogens psilocin, ibotenic acid, and muscimol: analytical methods and biologic activities. Ther Drug Monit. 2013 Aug;35(4):420-42. doi: 10.1097/FTD.0b013e31828741a5. Review. PubMed PMID: 23851905.
2: Krogsgaard-Larsen P, Honoré T, Hansen JJ, Curtis DR, Lodge D. Structure-activity studies on ibotenic acid and related muscimol analogues. Adv Biochem Psychopharmacol. 1981;27:285-94. Review. PubMed PMID: 7004116.
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