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Merck
CN

E2387

NECA

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

Synonym(s):

NECA

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About This Item

Empirical Formula (Hill Notation):
C12H16N6O4
CAS Number:
35920-39-9
Molecular Weight:
308.29
UNSPSC Code:
12352200
PubChem Substance ID:
24277684
NACRES:
NA.77
MDL number:
MFCD00069195

Key Documents

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Product Name

5′-(N-Ethylcarboxamido)adenosine, powder

SMILES string

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

InChI key

JADDQZYHOWSFJD-FLNNQWSLSA-N

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

form

powder

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

Quality Level

200

Gene Information

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

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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.

General description

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

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000340719
0000340719
0000219058
0000216316
0000216316

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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)
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.
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
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)
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
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