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Key Documents

E2387

Sigma-Aldrich

NECA

≥98% (TLC), powder, adenosine receptor agonist

Synonym(s):

NECA

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About This Item

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

product name

5′-(N-Ethylcarboxamido)adenosine, powder

form

powder

Quality Level

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

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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

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

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

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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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.
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
Shanshan Liu et al.
Protein science : a publication of the Protein Society, 25(12), 2209-2215 (2016-09-27)
The molecular chaperone Hsp90 facilitates the folding and modulates activation of diverse substrate proteins. Unlike other heat shock proteins such as Hsp60 and Hsp70, Hsp90 plays critical regulatory roles by maintaining active states of kinases, many of which are overactive
5-(N-ethylcarboxamido) adenosine desensitizes the A2b-adenosine receptor in lung circulation
Haynes Jr J, et al.
American Journal of Physiology. Heart and Circulatory Physiology, 276(6), H1877-H1883 (1999)

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