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119140

Sigma-Aldrich

NECA

≥99% (HPLC), solid, adenosine receptor agonist, Calbiochem®

Synonym(s):

Adenosine Receptor Agonist, NECA, (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C12H16N6O4
CAS Number:
Molecular Weight:
308.29
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Adenosine Receptor Agonist, NECA,

assay

≥99% (HPLC)

Quality Level

form

solid

potency

14 nM Ki

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 50 mM

shipped in

wet ice

storage temp.

2-8°C

InChI

1S/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6-,7+,8-,12?/m0/s1

InChI key

JADDQZYHOWSFJD-QQIVLSGASA-N

General description

A cell-permeable adenosine analog that acts a potent non-selective agonist of adenosine receptors (Ki = 14 nM, 20 nM, 2.4 µM and 6.2 nM for A1, A2A, A2B, A3, respectively). Increases intracellular cAMP production (EC50 = 3.1 µM in A2B expressing CHO cells). Shown to increase glucagon release in a dose-dependent manner and inhibit insulin release at low concentrations. Although at higher concentration some insulin release is observed. Also, displays a wide range adenosine-dependent effects, such as blocking platelet aggregation and inhibiting DNA synthesis. When administered at reperfusion, it is shown reduce infarction and block the formation of the mitochondrial permeability transition pore by activating p70S6 kinase.

Biochem/physiol Actions

Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Forster, K., et al. 2006. Basic Res. Cardiol.101, 319.
de Zwart, M., et al. 1998. Nucleosides Nucleotides.17, 969.
Phillis, J. et al. 1986, Pharm. Biochem. Behavior.24, 263
Durcan, M. J., et al. 1989. Pharmacol Biochem Behav.32, 487.
Bacher, S., et al. 1982. Naunyn Schmiedebergs Arch Pharmacol.329, 67.
Cusack, N., et al. 1981. Br J Pharm.72, 443.
Londos, C., et al. 1980. Proc Natl Acad Sci.77, 2551.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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