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Safety Information

I146

Sigma-Aldrich

IB-MECA

solid, ≥98% (HPLC)

Synonym(s):

1-Deoxy-1-[6-[((3-Iodophenyl)methyl)amino]-9H-purin-9-yl]-N-methyl-β-D-ribofuranuronamide, N6-(3-Iodobenzyl)adenosine-5′-N-methyluronamide

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About This Item

Empirical Formula (Hill Notation):
C18H19IN6O4
CAS Number:
152918-18-8
Molecular Weight:
510.29
MDL number:
MFCD00671785
UNSPSC Code:
12352200
PubChem Substance ID:
24277717
NACRES:
NA.32

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white

solubility

ethanol: >10 mg/mL (hot)
DMSO: >5 mg/mL
H2O: insoluble
aqueous acid: insoluble
aqueous base: insoluble

storage temp.

2-8°C

SMILES string

CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCc4cccc(I)c4)ncnc23

InChI

1S/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1

InChI key

HUJXGQILHAUCCV-MOROJQBDSA-N

Gene Information

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

Application

IB-MECA has been used for intraocular pressure and corneal thickness measurements in rabbits.

Biochem/physiol Actions

Selective A3 adenosine receptor agonist.

Legal Information

Sold under license from the National Institutes of Health.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

I146-IP:
I146-5MG:4548173990736
I146-BULK:
I146-VAR:
I146-25MG:4548173990743
I146-BULK-CR:

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Certificates of Analysis (COA)

Lot/Batch Number
042M4610V
117K4605
057K4631
051K4607

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John A Auchampach et al.
American journal of physiology. Heart and circulatory physiology, 285(2), H607-H613 (2003-04-12)
We examined the effect of the A3 adenosine receptor (AR) agonist IB-MECA on infarct size in an open-chest anesthetized dog model of myocardial ischemia-reperfusion injury. Dogs were subjected to 60 min of left anterior descending (LAD) coronary artery occlusion and
Athena M Keene et al.
Biochemical pharmacology, 80(2), 188-196 (2010-03-30)
Multivalent dendrimeric conjugates of GPCR ligands may have increased potency or selectivity in comparison to monomeric ligands, a phenomenon that was tested in a model of cytoprotection in mouse HL-1 cardiomyocytes. Quantitative RT-PCR indicated high expression levels of endogenous A(1)
P Mlejnek et al.
Acta physiologica (Oxford, England), 199(2), 171-179 (2010-02-04)
The sensitivity of cancer cells which exhibit multi-drug resistance phenotype to A3 adenosine receptor (A3AR) agonist N(6)-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide (IB-MECA) was studied. To establish direct relationship between P-glycoprotein (P-gp, ABCB1 and MDR1) expression and IB-MECA induced cell death, a straightforward method for
Michal Hofer et al.
International journal of radiation biology, 86(8), 649-656 (2010-07-01)
Research areas of 'post-exposure treatment' and 'cytokines and growth factors' have top priority among studies aimed at radiological nuclear threat countermeasures. The experiments were aimed at testing the ability of N(6)-(3-iodobenzyl)adenosine-5'-N-methyluronamide (IB-MECA), an adenosine A(3) receptor agonist, to modulate hematopoiesis
Jorge Guzman et al.
Inflammatory bowel diseases, 12(8), 766-789 (2006-08-19)
Adenosine A3 receptors (ADOA3Rs) are emerging as novel purinergic targets for treatment of inflammatory diseases. Our goal was to assess the protective effect of the ADOA3R agonist N(6)-(3-iodobenzyl)-adenosine-5-N-methyluronamide (IB-MECA) on gene dysregulation and injury in a rat chronic model of
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