NECA

NECA Basic information
Product Name:NECA
Synonyms:5'-N6-Ethylcarboxamidoadenosine;5'-ETHYLCARBOXAMIDOADENOSINE;1-(6-AMINO-9H-PURIN-9-YL)-1-DEOXY-N-ETHYL-BETA-D-RIBOFURANURONAMIDE;1-(6-amino-9h-purin-9-yl)-1-deoxy-n-ethylribofuranuronamidehemihydrate;1-(6-amino-9h-purin-9-yl)-1-deoxy-n-ethyl-ribofuranuronamidhemihydrate;5’-n(sup6)-ethylcarboxamidoadenosinehemihydrate;5’-n-ethylcarboxamidoadenosinehemihydrate;adenosine-5’-(n-ethyl)carboxamidehemihydrate
CAS:35920-39-9
MF:C12H16N6O4
MW:308.29
EINECS:
Product Categories:Bases & Related Reagents;Inhibitors;Nucleotides;Adenosine receptor
Mol File:35920-39-9.mol
NECA Structure
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.
pka12.93±0.70(Predicted)
form powder
color white
Stability:Hygroscopic
InChIKeyJADDQZYHOWSFJD-FLNNQWSLSA-N
CAS DataBase Reference35920-39-9
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 Information
ProviderLanguage
SigmaAldrich English
NECA Usage And Synthesis
Chemical PropertiesWhite Solid
UsesA potent adenosine receptor agonist. Inhibits platelet aggregation and is centrally active in vivo
UsesPotent adenosine receptor agonist with some affinity at A1 and A2 receptors
Uses5′-(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

DefinitionChEBI: A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group.
General DescriptionA cell-permeable adenosine analog that acts a potent non-selective agonist of adenosine receptors (Ki = 14 nM, 20 nM, 2.4 μM and 6.2 nM for A1, A2A, A2B, A3, respectively). Increases intracellular cAMP production (EC50 = 3.1 μM in A2B 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 ActivityPotent 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 ActionsReversible: yes
storageStore at +4°C
NECA Preparation Products And Raw materials
2-CHLORO-2',3'-O-ISOPROPYLIDENEADENOSINE-5'-N-ETHYLCARBOXAMIDE NECA CGS-21680 HYDROCHLORIDE CGS 21680, [CARBOXYETHYL-3H(N)]- DANSYL-NECA 2-IODO-NECA 5'-(N-CYCLOPROPYL)CARBOXAMIDOADENOSINE NECA 5'-N-[ADENINE-2,8-3H]- N6-BENZYL-NECA 5'-EthylcarboxaMido-2',3'-isopropylidene Adenosine he-neca 2-Chloro-NECA 5'-N-ETHYLCARBOXAMIDOADENOSINE, [ADENINE-2,8-3H]- CGS 21680 EB-47 DIHYDROCHLORIDE DIHYDRATE

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