Arecoline

Arecoline

Arecoline chemical structure

Arecoline is a naturally occurring alkaloid found in the areca nut, the fruit of the areca palm (Areca catechu). It is a potent cholinergic agent, acting as a partial agonist at muscarinic acetylcholine receptors. Arecoline is primarily known for its use in betel quid chewing, a practice common in many parts of Asia and the Pacific.

Chemical Properties

Arecoline is an oily liquid at room temperature, with the chemical formula C₈H₁₃NO₂. It is a member of the pyridine family of compounds and is structurally related to nicotine.

3D model of Arecoline

The compound is characterized by its pyridine ring and an ester functional group, which contribute to its biological activity. Arecoline is soluble in water and organic solvents, making it easily absorbed in the body when consumed.

Pharmacology

Arecoline acts as a parasympathomimetic agent, meaning it mimics the action of the parasympathetic nervous system. It primarily exerts its effects by binding to muscarinic acetylcholine receptors, leading to increased salivation, sweating, and intestinal motility. These effects are similar to those produced by acetylcholine, the natural ligand for these receptors.

Uses

In traditional medicine, arecoline has been used for its stimulant properties. It is also used in veterinary medicine as an anthelmintic to expel parasitic worms in animals.

Health Effects

Chronic use of arecoline through betel quid chewing is associated with several health risks, including an increased risk of oral cancer, esophageal cancer, and cardiovascular disease. The World Health Organization classifies arecoline as a Group 1 carcinogen.

Aortography image showing calcification in the aorta

Synthesis

Arecoline can be synthesized through several chemical pathways. One common method involves the reaction of arecaidine with methyl iodide.

Synthesis pathway of Arecoline

An alternative synthesis involves the use of acrolein and methylamine as starting materials.

Alternative synthesis of Arecoline

Related Pages

• Areca nut
• Betel quid
• Muscarinic acetylcholine receptor
• Cholinergic
• Carcinogen