35920-39-9

Basic information

• Product Name: NECA
• Synonyms: b-D-RibofuranuronaMide, 1-(6-aMino-9H-purin-9-yl)-1-deoxy-N-ethyl-;5'-N6-Ethylcarboxamidoadenosine;D-NECA;NECA,5′-(N-Ethylcarboxamido)adenosine;Adenosine Receptor Agonist, NECA;5'-(N-ETHYLCARBOXAMIDO)-ADENOSINE;5'-ETHYLCARBOXAMIDOADENOSINE;1-(6-AMINO-9H-PURIN-9-YL)-1-DEOXY-N-ETHYL-BETA-D-RIBOFURANURONAMIDE
• CAS NO: 35920-39-9
• Molecular Formula: C₁₂H₁₆N₆O₄
• Molecular Weight: 308.29
• Product Categories: Bases & Related Reagents;Inhibitors;Nucleotides;Adenosine receptor
• Mol File: 35920-39-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 229-231°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/powder
• Density: 1.87g/cm³
• Storage Temp.: 2-8°C
• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2 mg/mL
• PKA: 12.93±0.70(Predicted)
• CAS DataBase Reference: NECA(CAS DataBase Reference)
• NIST Chemistry Reference: NECA(35920-39-9)
• EPA Substance Registry System: NECA(35920-39-9)

Safety Data

• Hazard Codes: T+
• 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
• Hazardous Substances Data: 35920-39-9(Hazardous Substances Data)

Usage

Description

NECA, also known as 5′-(N-Ethylcarboxamido)adenosine, is a cell-permeable adenosine analog that acts as a potent non-selective agonist of adenosine receptors. It is a white solid with a wide range of adenosine-dependent effects, such as blocking platelet aggregation and inhibiting DNA synthesis. NECA has been shown to increase intracellular cAMP production and modulate the release of glucagon and insulin.

Uses

Used in Pharmaceutical Research:
NECA is used as a potent adenosine receptor agonist with some affinity at A1 and A2 receptors for various pharmaceutical applications, including the inhibition of platelet aggregation and central activity in vivo.
Used in Receptor Purification:
NECA is used as a tool for the purification of human adenosine A2Areceptor (A2AR) in decylmaltoside (DM) to determine nonspecific binding of adenosine receptors.
Used in Investigating Receptor Mechanisms:
NECA is used to investigate the adenosine 2B receptor (RA2B) mechanism of action by competition assay.
Used in Cell Signaling Studies:
NECA is used to increase intracellular cAMP production (EC50 = 3.1 μM in A2B expressing CHO cells) and study the effects of adenosine receptor activation on cell signaling pathways.
Used in Cardiovascular Research:
When administered at reperfusion, NECA is shown to reduce infarction and block the formation of the mitochondrial permeability transition pore by activating p70S6 kinase, making it useful in cardiovascular research and potential therapeutic applications.
Used in Drug Delivery Systems:
NECA can be employed in the development of novel drug delivery systems to enhance its applications and efficacy in various therapeutic areas, such as cancer treatment, by improving its delivery, bioavailability, and therapeutic outcomes.

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

Upstream product

• 75-04-7 ethylamine 
• 41110-82-1 adenosine-5'-carboxylic acid 2-chloroethyl ester 
• 35803-57-7 ethyl adenosine-5'-carboxylate 
• 39491-53-7 5'-N-ethyl-2',3'-O-isopropylidenecarboxamidoadenosine 
• 19234-66-3 2',3'-isopropylideneadenosine-5'-carboxylic acid 
• 159647-45-7 (3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 4-nitro-phenyl ester 
• 362-75-4 2',3'-isopropylidene adenosine 
• 3415-09-6 adenosine 5'-carboxylic acid 

Downstream Products

• 58048-26-3 2',3'-di-O-acetyladenosine-5'-(N-rthyl)carboxamide 
• 152918-32-6 N⁶-benzyl-5'-N-ethylcarboxamidoadenosine 
• 72209-27-9 (2S,3S,4R,5R)-5-(6-Amino-1-oxy-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide 

Relevant articles and documents

Ring opening reactions: Synthesis of AICAR analogs as potential antimetabolite agents

In an attempt to improve the A2A selectivity of the 2-(aryl)alkylthio derivatives of adenosine, we planned the synthesis of the corresponding derivatives of the 5′-N-ethylcarboxamidoadenosine (NECA). For this purpose, we designed the synthesis of 2-mercapto-NECA to be pursued by means of an opening-closure method. We obtained the open AICAR analog; however, ring closure efforts failed to give the desired compound. The newly synthesized AICAR derivative could potentially be endowed with antiviral or antitumoral activity. Copyright Taylor & Francis, Inc.

N6-substituted N-alkyladenosine-5'-uronamides: bifunctional ligands having recognition groups for A1 and A2 adenosine receptors.

The coronary vasoactivity of N-ethyl-1'-deoxy-1'-(6-amino-9H-purin-9-yl)-beta-D-ribofuranuronamide (NECA, 1) is over 2 orders of magnitude greater than that of adenosine, and the vasoactivity of certain N6-substituted adenosines is as much as 1 order of m

Adenosine-5'-carboxylic acid amides

Adenosine-5'-carboxylic acid amides represented by the formula STR1 wherein R1 and R2 are each selected from the group consisting of hydrogen, loweralkyl, lowerhaloalkyl, lowerhydroxyalkyl, lowercycloalkyl, loweralkylcycloalkyl, loweralkenyl, lowerhaloalkenyl, lowerhydroxyalkenyl, loweralkynyl, lowerhaloalkynyl, benzylamino, phenyl, loweralkylphenyl, loweralkoxyloweralkyl, substituted phenyl, 2-methylfuran or di(C1 -C4)alkylamino(C1 -C4)alkyl, adamantyl or R1 and R2 taken together form a 5 or 6 membered heterocyclic moiety; R3 and R4 are hydrogen or acyl, or taken together form an isopropylidene or a benzylidene group; or a pharmaceutically acceptable acid addition salt thereof.