Ibotenic Acid
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MedKoo CAT#: 561191

CAS#: 2552-55-8

Description: Ibotenic Acid is a potent excitatory amino acid agonist. Ibotenic Acid causes motor depression, ataxia, and changes in mood. Ibotenic Acid is also a neurotoxin.


Chemical Structure

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Ibotenic Acid
CAS# 2552-55-8

Theoretical Analysis

MedKoo Cat#: 561191
Name: Ibotenic Acid
CAS#: 2552-55-8
Chemical Formula: C5H6N2O4
Exact Mass: 158.03
Molecular Weight: 158.113
Elemental Analysis: C, 37.98; H, 3.83; N, 17.72; O, 40.47

Price and Availability

Size Price Availability Quantity
5mg USD 360
10mg USD 650 2 Weeks
25mg USD 1250 2 Weeks
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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

Appearance: Solid powder

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

More Info:

Product Data:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 5.0 31.62
Water 3.3 20.81

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.

Recalculate based on batch purity %
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.

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