Arecoline: Difference between revisions

Latest revision as of 11:46, 23 March 2025

Arecoline[edit]

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[edit]

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.

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[edit]

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[edit]

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[edit]

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[edit]

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

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

Related Pages[edit]

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-'''Arecoline''' is a [[alkaloid]] that is found in the [[betel nut]] of the [[Areca palm]]. It is a base, with a pKa of 6.8. Arecoline is a [[muscarinic]] partial agonist, which can stimulate the [[muscarinic acetylcholine receptor]].
+==Arecoline==
-==Chemistry==
+[[File:Arekolina.svg|Arecoline chemical structure|thumb|right]]
-Arecoline is an oily liquid that is colorless to yellowish-brown. It is soluble in water, alcohol, and ether. The chemical formula of arecoline is C8H13NO2, and its molecular weight is 155.19 g/mol. It is a tertiary amine, with a single nitrogen atom bonded to three carbon atoms.
+'''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 C<sub>8</sub>H<sub>13</sub>NO<sub>2</sub>. It is a member of the [[pyridine]] family of compounds and is structurally related to [[nicotine]].
+[[File:Arecoline3d.png|3D model of Arecoline|thumb|left]]
+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 has been found to have several pharmacological effects. It is a [[muscarinic]] partial agonist, which means it can stimulate the [[muscarinic acetylcholine receptor]]. This can lead to a variety of effects, including increased salivation, sweating, and bronchial secretions, as well as a decrease in heart rate and blood pressure.
-==Toxicity==
+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.
-Arecoline is toxic and can cause a variety of health problems. It is a known [[carcinogen]], and long-term use can lead to oral cancer. It can also cause a variety of other health problems, including liver damage, heart disease, and neurological problems.
 ==Uses==
-Arecoline has been used in traditional medicine for a variety of purposes. It has been used as a [[stimulant]], a [[diuretic]], and a remedy for [[worm infestations]]. However, due to its toxicity, its use is generally discouraged in modern medicine.
-==See also==
+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]].
+[[File:Moenckeberg.jpg|Aortography image showing calcification in the aorta|thumb|right]]
+==Synthesis==
+Arecoline can be synthesized through several chemical pathways. One common method involves the reaction of [[arecaidine]] with [[methyl iodide]].
+[[File:Arecoline_synthesis.svg|Synthesis pathway of Arecoline|thumb|left]]
+An alternative synthesis involves the use of [[acrolein]] and [[methylamine]] as starting materials.
+[[File:Arecoline_synthesis2.svg|Alternative synthesis of Arecoline|thumb|right]]
+==Related Pages==
 * [[Areca nut]]
+* [[Betel quid]]
 * [[Muscarinic acetylcholine receptor]]
-* [[Alkaloid]]
+* [[Cholinergic]]
+* [[Carcinogen]]
 [[Category:Alkaloids]]
-[[Category:Muscarinic agonists]]
+[[Category:Cholinergics]]
 [[Category:Carcinogens]]
-{{stub}}