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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
Form:
powder
Quality level:
200
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Product Name

5′-(N-Ethylcarboxamido)adenosine, powder

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)

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[1]

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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This Item
P4532A1784A0779
5′-(N-Ethylcarboxamido)adenosine powder

Sigma-Aldrich

E2387

5′-(N-Ethylcarboxamido)adenosine

(−)-N6-(2-Phenylisopropyl)adenosine solid

Sigma-Aldrich

P4532

(−)-N6-(2-Phenylisopropyl)adenosine

Aminopterin powder

Sigma-Aldrich

A1784

Aminopterin

p-Aminoclonidine hydrochloride solid

Sigma-Aldrich

A0779

p-Aminoclonidine hydrochloride

form

powder

form

solid

form

powder

form

solid

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

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

solubility

H2O: slightly soluble 0.3 mg/mL (Solutions may be stored for several days at 4°C.), 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.6 mg/mL (Solutions may be stored for several days at 4°C.)

solubility

2 M NaOH: 50 mg/mL (Solutions may be stored for 1-2 days at 4°C.)

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.4 mg/mL (Solutions may be stored for several days at 4 °C), boiling water: 100 mg/mL (Solutions may be stored for several days at 4 °C), 0.1 M HCl: soluble (Solutions may be stored for several days at 4 °C), methanol: soluble (Solutions may be stored for several days at 4 °C)

color

white

color

white

color

light yellow to yellow-brown

color

white

Gene Information

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

Gene Information

human ... ADORA1(134)

Gene Information

human ... FPGS(2356)
mouse ... Fpgs(14287)

Gene Information

human ... ADRA2A(150), ADRA2B(151), ADRA2C(152)

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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
0000216316
0000340719
0000216316
0000340719
0000219058

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Adenosine mediates immunosuppression within the tumor microenvironment through triggering adenosine 2A receptors (A2AR) on immune cells. To determine whether this pathway could be targeted as an immunotherapy, we performed a phase I clinical trial with a small-molecule A2AR antagonist. We
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Global Trade Item Number

SKUGTIN
E2387-50MG04061833602607

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