Skip to Content
Merck
CN
All Photos(1)

Documents

E2387

Sigma-Aldrich

5′-(N-Ethylcarboxamido)adenosine

powder

Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
NECA
Empirical Formula (Hill Notation):
C12H16N6O4
CAS Number:
35920-39-9
Molecular Weight:
308.29
MDL number:
MFCD00069195
UNSPSC Code:
12352200
PubChem Substance ID:
24277684
NACRES:
NA.77

form

powder

Quality Level

200

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2 mg/mL (Solutions may be stored for several days at 4 °C.)
DMSO: 14 mg/mL (Solutions may be stored for several days at 4 °C.)
0.1 M HCl: 3.4 mg/mL (Solutions may be stored for several days at 4 °C.)
H2O: insoluble
ethanol: soluble (Solutions may be stored for several days at 4 °C.)

storage temp.

2-8°C

SMILES string

CCNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23

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-FLNNQWSLSA-N

Gene Information

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora2b(29316) , Adora3(25370)

Looking for similar products? Visit Product Comparison Guide

General description

5′-(N-Ethylcarboxamido)adenosine stimulates vasodilation in the pulmonary circulation through A2-adenosine-receptor activation.

Application

5′-(N-Ethylcarboxamido)adenosine has been used:
  • for the purification of human adenosine A2Areceptor (A2AR) in decylmaltoside (DM)
  • to determine nonspecific binding of adenosine receptors
  • to investigate adenosine 2B receptor (RA2B) mechanism of action by competition assay

Biochem/physiol Actions

Potent adenosine receptor agonist with nearly equal affinity at A1 and A2 receptors.

Features and Benefits

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P264 - P301 + P310

Hazard Classifications

Acute Tox. 2 Oral

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

Nanomolar anti-sickling compounds identified by ligand-based pharmacophore approach
Paz OS, et al.
European Journal of Medicinal Chemistry, 136, 487-496 (2017)
Olov Andersson et al.
Cell metabolism, 15(6), 885-894 (2012-05-23)
Diabetes can be controlled with insulin injections, but a curative approach that restores the number of insulin-producing β cells is still needed. Using a zebrafish model of diabetes, we screened ~7,000 small molecules to identify enhancers of β cell regeneration.
Docking screens for dual inhibitors of disparate drug targets for Parkinson?s disease
Jaiteh M, et al.
Journal of Medicinal Chemistry, 61(12), 5269-5278 (2018)
Expression, purification and crystallisation of the adenosine A2A Receptor Bound to an Engineered Mini G Protein
Carpenter B and Tate CG
Bio-protocol, 7(8) (2017)
Jhansi Rani Nathan et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 84, 1406-1418 (2016-11-03)
Angiogenesis, formation of new blood vessels is an important process involved in neovascular diseases and tumor progression. Understanding and defining novel therapeutic targets of neovascular diseases like retinopathy of prematurity, diabetic retinopathy and age-related macular degeneration have been hindered by
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