MilliporeSigma
All Photos(1)

Documents

119140

Sigma-Aldrich

Adenosine Receptor Agonist, NECA

Sign Into View Organizational & Contract Pricing

Synonym(s):
Adenosine Receptor Agonist, NECA, (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamide
Empirical Formula (Hill Notation):
C12H16N6O4
CAS Number:
Molecular Weight:
308.29
MDL number:

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

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service