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A236

Sigma-Aldrich

AB-MECA

solid

Synonym(s):

N6-(4-Aminobenzyl)-9-[5-(methylcarbonyl)-β-D-ribofuranosyl]adenine, N6-(4-Aminobenzyl)-N-methylcarboxamidoadenosine

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About This Item

Empirical Formula (Hill Notation):
C18H21N7O4
CAS Number:
152918-26-8
Molecular Weight:
399.40
UNSPSC Code:
12352200
PubChem Substance ID:
24277694
NACRES:
NA.77

form

solid

Quality Level

100

color

off-white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.3 mg/mL
ethanol: 1 mg/mL
DMSO: 10 mg/mL
dilute aqueous base: 3.5 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCc4ccc(N)cc4)ncnc23

InChI

1S/C18H21N7O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-2-4-10(19)5-3-9/h2-5,7-8,12-14,18,26-27H,6,19H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1

InChI key

LDYMCRRFCMRFKB-MOROJQBDSA-N

Gene Information

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

Biochem/physiol Actions

High affinity 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
C Gallo-Rodriguez et al.
Journal of medicinal chemistry, 37(5), 636-646 (1994-03-04)
Adenosine analogues modified at the 5'-position as uronamides and/or as N6-benzyl derivatives were synthesized. These derivatives were examined for affinity in radioligand binding assays at the newly discovered rat brain A3 adenosine receptor and at rat brain A1 and A2a

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