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C277

Sigma-Aldrich

Chloro-IB-MECA

solid, ≥98% (HPLC)

Synonym(s):

2-Chloro-N6-(3-iodobenzyl)-adenosine-5′-N-methyluronamide, Cl-IB-MECA

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About This Item

Empirical Formula (Hill Notation):
C18H18ClIN6O4
CAS Number:
163042-96-4
Molecular Weight:
544.73
MDL number:
MFCD01861178
UNSPSC Code:
12352200
PubChem Substance ID:
24278354
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >20 mg/mL

SMILES string

CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc23

InChI

1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1

InChI key

IPSYPUKKXMNCNQ-PFHKOEEOSA-N

Gene Information

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

Biochem/physiol Actions

2-chloro-N(6)-(3-iodobenzyl)adenosine-5′-N-methylcarboxamide (Cl-IB-MECA) is a adenosine receptor. It protects against myocardial ischemia/reperfusion injury in mice.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
026M4612V
097K4617
129H0935
129H0934

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Cl-IB-MECA [2-Chloro-N6-(3-iodobenzyl) adenosine-5?-N-methylcarboxamide] Reduces Ischemia/Reperfusion Injury in Mice by Activating the A Adenosine Receptor
Ge ZD, et al.
Journal of Pharmacology and Experimental Therapeutics, 319(3), 1200-1210 (2006)
Y Yao et al.
Biochemical and biophysical research communications, 232(2), 317-322 (1997-03-17)
The effects of novel, selective adenosine (ADO) A3 receptor antagonists of diverse structure on cells of the human HL-60 leukemia and U-937 lymphoma cell lines were examined. Both 3-ethyl 5-benzyl 2-methyl-6-phenyl-4-phenylethynyl-1,4-(+/-)-dihydropyridine-3, 5-dicarboxylate (MRS 1191, 0.5 microM) and 6-carboxy-methyl-5, 9-dihydro-9-methyl-2-phenyl-[1,2,4]-triazolo [5,1-a][2,7]naphthyridine
The A3 adenosine receptor agonist 2-Cl-IB-MECA facilitates epileptiform discharges in the CA3 area of immature rat hippocampal slices
Laudadio MA, et al.
Epilepsy Research, 59(2), 83-94 (2004)
K Stambaugh et al.
The American journal of physiology, 273(1 Pt 2), H501-H505 (1997-07-01)
The possible cardioprotective roles of adenosine A1 and A3 receptors were investigated in a cardiac myocyte model of injury. The adenosine A3 receptor is a novel cardiac receptor capable of mediating potentially important cardioprotective functions. Prolonged hypoxia with glucose deprivation
T V Dunwiddie et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 17(2), 607-614 (1997-01-15)
The adenosine A3 receptor is expressed in brain, but the consequences of activation of this receptor on electrophysiological activity are unknown. We have characterized the actions of a selective adenosine A3 receptor agonist, 2-chloro-N6-(3-lodobenzyl)-adenosine-5'-N-methyluronamide (Cl-IB-MECA), and a selective A3 receptor
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