Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

M3763

Sigma-Aldrich

Adenosine 5′-(α,β-methylene)diphosphate

ADP analog

Synonym(s):

α,β-Methyleneadenosine 5′-diphosphate, ADP[α,β-CH2], AMP-CP

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C11H17N5O9P2
CAS Number:
3768-14-7
Molecular Weight:
425.23
Beilstein:
633678
EC Number:
223-194-0
MDL number:
MFCD00042991
UNSPSC Code:
41106305
PubChem Substance ID:
24896872
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

Assay

≥99% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)CP(O)(O)=O)[C@@H](O)[C@H]3O

InChI

1S/C11H17N5O9P2/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1

InChI key

OLCWZBFDIYXLAA-IOSLPCCCSA-N

Looking for similar products? Visit Product Comparison Guide

Application

Adenosine 5′-(α,β-methylene)diphosphate has been used as a component of culture media, to study its effects as an inhibitor of cluster of differentiation 73 (CD73) and adenosinergic signaling regulation via CD73 or ecto-5′-nucleotidase.

Reconstitution

soluble in water up to Approx. 50 mg/ml with heating

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Ischemia-driven expression of CD73 confers tissue protection during liver ischemia/reperfusion.
Caldwell CC, Lentsch AB.
Gastroenterologie Clinique Et Biologique, 135, 1460-1462 (2008)
Svetlana T Mihaylova-Todorova et al.
The Journal of pharmacology and experimental therapeutics, 302(3), 992-1001 (2002-08-17)
Previously, we have demonstrated that stimulation of the sympathetic nerves of the guinea pig vas deferens evokes release not only of the cotransmitters ATP and norepinephrine but also of soluble nucleotidases that break down extracellular ATP, ADP, and AMP into
Félix A Soares et al.
Brain research, 1005(1-2), 182-186 (2004-03-27)
Studies on the purinergic system normally deal with adenine-based purines, namely, adenine nucleotides and adenosine. However, a guanine-based purinergic system may also have important neuromodulatory roles. Guanine-based purines exert trophic effects on neural cells, protect brain slices in a model
J Karczewska et al.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society, 58(2), 321-333 (2007-07-12)
ATP and adenosine are important extracellular regulators of glomerular functions. In this study, ATP release from glomeruli suspension and its extracellular metabolism were investigated. Basal extraglomerular ATP concentration (1nM) increased several fold during inhibition of ecto-ATPase activity, reflecting the basal
L Jensen et al.
Angiogenesis, 7(3), 255-267 (2004-12-21)
The role of muscle contraction, prostanoids, nitric oxide and adenosine in the regulation of vascular endothelial growth factor (VEGF), basic fibroblast growth factor (bFGF) and endothelial cell proliferative compounds in skeletal muscle cell cultures was examined. VEGF and bFGF mRNA
View All Related Papers

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