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Merck
CN

I145

I-AB-MECA

solid

Synonym(s):

1-[6-[[(4-Amino-3-iodophenyl)methyl]amino]-9H-purin-9-yl]-1-deoxy-N-methyl-β-D-ribofuranuronamide, 3-Iodo-4-aminobenzyl-5′-N-methylcarboxamidoadenosine, N6-(4-Amino-3-iodobenzyl)-5′-N-methylcarbamoyladenosine

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About This Item

Empirical Formula (Hill Notation):
C18H20IN7O4
CAS Number:
152918-27-9
Molecular Weight:
525.30
NACRES:
NA.77
PubChem Substance ID:
24895933
UNSPSC Code:
12352200
MDL number:
MFCD00671784

Key Documents

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InChI

1S/C18H20IN7O4/c1-21-17(29)14-12(27)13(28)18(30-14)26-7-25-11-15(23-6-24-16(11)26)22-5-8-2-3-10(20)9(19)4-8/h2-4,6-7,12-14,18,27-28H,5,20H2,1H3,(H,21,29)(H,22,23,24)/t12-,13+,14-,18+/m0/s1

SMILES string

CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCc4ccc(N)c(I)c4)ncnc23

InChI key

LOGOEBMHHXYBID-MOROJQBDSA-N

form

solid

color

off-white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2 mg/mL, DMSO: 10 mg/mL, 0.1 M NaOH: 2 mg/mL, 0.1 M HCl: 7 mg/mL, H2O: insoluble

storage temp.

−20°C

Gene Information

human ... ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Biochem/physiol Actions

Reference standard for radioiodinated I-AB-MECA, a widely used, high affinity radioligand for the A3 adenosine receptor.

Legal Information

Sold under license from the National Institutes of Health.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
048H4644

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D K Von Lubitz et al.
European journal of pharmacology, 275(1), 23-29 (1995-02-24)
We have previously shown that acute preischemic adenosine A3 receptor stimulation results in an increased postischemic damage, while chronic stimulation of this receptor diminishes it. Since several pathophysiological phenomena are common for both ischemia and seizures, we have explored the
M E Olah et al.
Molecular pharmacology, 45(5), 978-982 (1994-05-01)
The rat A3 adenosine receptor (AR) is a recently characterized AR subtype cloned from testis and brain cDNA libraries. N6-2-(4-Amino-3-[125I]iodophenyl)ethyladenosine, a high affinity A1AR agonist, has served as the only radioligand available for study of the A3AR. The relatively low
K A Jacobson et al.
FEBS letters, 336(1), 57-60 (1993-12-20)
The behavioral effects of a selective A3 adenosine receptor agonist 3-IB-MECA (N6-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine) in mice and the localization of radioligand binding sites in mouse brain were examined. Low levels of A3 adenosine receptors were detected in various regions of the mouse

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