Structure via PubChem · Public domain (PubChem)
arecoline
Sign in to saveAlso known as methylarecaiden, methylarecaidin, taeniolin, arecholine, arecaline, arecaidine methyl ester, arekolin
Arecoline is a cholinergic agent, stimulant, and naturally occurring alkaloid found in areca (betel) nuts of the areca palm (Areca catechu) found in South and Southeast Asia. Its effects, depending on the dose, include stimulation, alertness, increased concentration, cognitive enhancement, elation, euphoria, pro-sexual effects, relaxation, reduced anxiety, and sedation, as well as addiction and withdrawal symptoms upon discontinuation. Its effects are described as subtle and it has been likened to a strong cup of coffee. There are also other active constituents of areca nuts, but arecoline is
Chemical data
- Formula
- C8H13NO2
- Molecular weight
- 155.19 g/mol
- IUPAC name
- methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
- SMILES
- CN1CCC=C(C1)C(=O)OC
- InChIKey
- HJJPJSXJAXAIPN-UHFFFAOYSA-N
- XLogP
- 0.3
- Polar surface area
- 29.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
1,737 papers- DARK Classics in Chemical Neuroscience: Arecoline.ACS chemical neuroscience · 2019
- Assessing the carcinogenic potential and molecular mechanisms of arecoline in human lungs: from in silico methods to in vitro validation.Ecotoxicology and environmental safety · 2025
- Comprehensive Insights into Arecoline Hydrobromide: Pharmacology, Toxicity, and Pharmacokinetics.Medical science monitor : international medical journal of experimental and clinical research · 2024
- Arecoline Alleviates Depression via Gut-Brain Axis Modulation, Neurotransmitter Balance, Neuroplasticity Enhancement, and Inflammation Reduction in CUMS Mice.Journal of agricultural and food chemistry · 2025
- A Review on Role of Arecoline and Its Metabolites in the Molecular Pathogenesis of Oral Lesions with an Insight into Current Status of Its Metabolomics.Prague medical report · 2020
via PubMed
Wikidata facts
- Mass
- 155.094629
Show 3 more facts
- chemical formula
- C₈H₁₃NO₂
- canonical SMILES
- CN1CCC=C(C1)C(=O)OC
- Commons category
- Arecoline
via Wikidata · CC0
~13 min read
Article
16 sectionsContents
- Uses
- Recreational
- Medical
- Traditional medicine
- Toxicity
- Mechanisms of toxicity
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Synthesis
- Chemical precursor
- Analogues
- Research
- Veterinary use
- References
Arecoline is a cholinergic agent, stimulant, and naturally occurring alkaloid found in areca (betel) nuts of the areca palm (Areca catechu) found in South and Southeast Asia. Its effects, depending on the dose, include stimulation, alertness, increased concentration, cognitive enhancement, elation, euphoria, pro-sexual effects, relaxation, reduced anxiety, and sedation, as well as addiction and withdrawal symptoms upon discontinuation. Its effects are described as subtle and it has been likened to a strong cup of coffee. There are also other active constituents of areca nuts, but arecoline is the key active component, with a percentage of ~0.3 to 0.6%. Areca nuts are administered by chewing for 5 to 20minutes without swallowing.
Side effects of arecoline include hypersalivation, hypotension, vertigo, miosis, tremor, and bradycardia, among others. Other adverse effects can include extrapyramidal syndrome and seizures. Addiction and dependence can occur, with withdrawal symptoms including mood swings, anxiety, irritability, and insomnia. Rarely, psychosis can occur during withdrawal in heavy users. Areca nut use, the primary method of consuming arecoline, is highly associated with oral disease and oral cancer. Overdose of arecoline can be treated with antimuscarinic drugs like atropine or scopolamine.