NECA Chemical Properties

Melting point:

229-231°C

Density 

1.87±0.1 g/cm3(Predicted)

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.

pka

12.93±0.70(Predicted)

form 

powder

color 

white

Stability:

Hygroscopic

InChIKey

JADDQZYHOWSFJD-FLNNQWSLSA-N

CAS DataBase Reference

35920-39-9

Safety Information

Hazard Codes 

T+

Risk Statements 

28

Safety Statements 

22-26-36-45

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

VJ2232000

HazardClass 

6.1(a)

PackingGroup 

I

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

NECA Usage And Synthesis

Chemical Properties

White Solid

Uses

A potent adenosine receptor agonist. Inhibits platelet aggregation and is centrally active in vivo

Uses

Potent adenosine receptor agonist with some affinity at A1 and A2 receptors

Uses

5′-(N-Ethylcarboxamido)adenosine has been used:

• for the purification of human adenosine A_2Areceptor (A_2AR) in decylmaltoside (DM)
• to determine nonspecific binding of adenosine receptors
• to investigate adenosine 2B receptor (RA2B) mechanism of action by competition assay

Definition

ChEBI: A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group.

General Description

A cell-permeable adenosine analog that acts a potent non-selective agonist of adenosine receptors (K_i = 14 nM, 20 nM, 2.4 μM and 6.2 nM for A₁, A_2A, A_2B, A₃, respectively). Increases intracellular cAMP production (EC₅₀ = 3.1 μM in A_2B expressing CHO cells). Shown to increase glucagon release in a dose-dependent manner and inhibit insulin release at low concentrations. Although at higher concentration some insulin release is observed. Also, displays a wide range adenosine-dependent effects, such as blocking platelet aggregation and inhibiting DNA synthesis. When administered at reperfusion, it is shown reduce infarction and block the formation of the mitochondrial permeability transition pore by activating p70S6 kinase.

Biological Activity

Potent adenosine receptor agonist (K i values are 14, 20 and 6.2 nM for human A 1 , A 2A and A 3 receptors respectively; EC 50 = 2.4 μ M for human A 2B ). Inhibits platelet aggregation and is centrally active in vivo .

Biochem/physiol Actions

Reversible: yes

storage

Store at +4°C

NECA(35920-39-9)Related Product Information

• he-neca
• 2-IODO-NECA
• 5'-EthylcarboxaMido-2',3'-isopropylidene Adenosine
• 2-Chloro-NECA
• NECA 5'-N-[ADENINE-2,8-3H]-
• N6-BENZYL-NECA
• CGS 21680, [CARBOXYETHYL-3H(N)]-
• 2-CHLORO-2',3'-O-ISOPROPYLIDENEADENOSINE-5'-N-ETHYLCARBOXAMIDE
• EB-47 DIHYDROCHLORIDE DIHYDRATE
• CGS 21680
• NECA
• 5'-(N-CYCLOPROPYL)CARBOXAMIDOADENOSINE
• DANSYL-NECA
• 5'-N-ETHYLCARBOXAMIDOADENOSINE, [ADENINE-2,8-3H]-
• CGS-21680 HYDROCHLORIDE