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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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Vijay B Urmaliya et al.
Journal of cardiovascular pharmacology, 53(5), 424-433 (2009-04-01)
Extracellular adenosine concentrations increase within the heart during ischemia, and any exogenous adenosine receptor agonists therefore work in the context of significant local agonist concentrations. We evaluated the interactions between A1, A2A, A2B, and A3 receptors in the presence and
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
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
L Rath-Wolfson et al.
Clinical and experimental rheumatology, 24(4), 400-406 (2006-09-08)
The anti-inflammatory effect of adenosine is partially mediated via the A3 adenosine receptor (A3AR), a Gi protein associated cell surface receptor. The highly selective A3AR agonist, IB-MECA was earlier shown to prevent the clinical and pathological manifestations of arthritis in
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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