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Merck

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:
Molecular Weight:
308.29
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Form:
powder
Quality level:
Technical Service
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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

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.


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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

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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Nanomolar anti-sickling compounds identified by ligand-based pharmacophore approach
Paz OS, et al.
European Journal of Medicinal Chemistry, 136, 487-496 (2017)
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)
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)