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Key Documents

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:
Molecular Weight:
510.29
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.32

Quality Level

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

Application

IB-MECA has been used for intraocular pressure and corneal thickness measurements in rabbits.[1]

Biochem/physiol Actions

Selective A3 adenosine receptor agonist.[2]

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

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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
Zhelong Xu et al.
Cardiovascular drug reviews, 24(3-4), 227-238 (2007-01-12)
The adenosine A(3) receptor plays an important role in ischemic preconditioning. Activation of the adenosine A(3) receptor with its agonists induces both early and late pharmacological preconditioning through various mechanisms. As the first potent and selective adenosine A(3) receptor agonist
Lea Madi et al.
Experimental dermatology, 22(1), 74-77 (2012-10-24)
A3 adenosine receptor, A3AR, belongs to the Gi proteins coupled receptors. Activation of A3AR by its agonist, IB-MECA, decreases cAMP and was expected to reduce melanin level. Unexpectedly, B16 melanoma cells exposed to IB-MECA increased melanin levels in a dose-dependent

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