5'-N-ethylcarboxamidoadenosine

5'-N-Ethylcarboxamidoadenosine (NECA) is a potent adenosine receptor agonist that is widely used in pharmacology and biochemistry research. It is a synthetic derivative of adenosine, a naturally occurring nucleoside that plays a crucial role in various physiological processes, including neurotransmission, vasodilation, and immune response.

Chemical Structure and Properties

NECA is chemically classified as a purine nucleoside analog. Its structure consists of an adenosine molecule with an ethylcarboxamido group attached to the 5' position of the ribose sugar. This modification enhances its affinity for adenosine receptors, making it a valuable tool for studying receptor function.

The chemical formula of NECA is C14H19N5O5, and it has a molecular weight of 337.33 g/mol. It is typically used in the form of a white to off-white powder that is soluble in water and other polar solvents.

Mechanism of Action

NECA acts as a non-selective agonist for all four subtypes of adenosine receptors: A1, A2A, A2B, and A3. These receptors are G protein-coupled receptors (GPCRs) that mediate various physiological effects of adenosine.

• A1 Receptors: Activation of A1 receptors by NECA can lead to inhibition of adenylate cyclase, resulting in decreased levels of cyclic AMP (cAMP) and subsequent physiological effects such as cardiac depression and neuroprotection.
• A2A and A2B Receptors: NECA's action on A2A and A2B receptors typically results in the stimulation of adenylate cyclase, increasing cAMP levels. This can lead to vasodilation, anti-inflammatory effects, and modulation of neurotransmitter release.
• A3 Receptors: The activation of A3 receptors by NECA is associated with various effects, including cardioprotection and anti-inflammatory responses.

Applications in Research

NECA is extensively used in research to study the physiological and pharmacological roles of adenosine receptors. It serves as a standard reference compound in experiments designed to elucidate receptor function, signaling pathways, and potential therapeutic applications.

• Cardiovascular Research: NECA is used to investigate the role of adenosine receptors in cardioprotection and ischemia-reperfusion injury.
• Neuroscience: Researchers utilize NECA to study adenosine's effects on synaptic transmission, neuroprotection, and neurodegenerative diseases.
• Immunology: NECA helps in understanding the modulation of immune response by adenosine receptors, particularly in the context of inflammation and autoimmune diseases.

Safety and Handling

As with many research chemicals, NECA should be handled with care. Appropriate safety protocols should be followed, including the use of personal protective equipment (PPE) such as gloves and goggles. It should be stored in a cool, dry place, away from light and moisture.

Also see

• Adenosine receptor
• Adenosine
• G protein-coupled receptor
• Cyclic AMP
• Cardioprotection