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Arecoline
Identification
- Name
- Arecoline
- Accession Number
- DB04365
- Description
An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Arecoline (DB04365)
- Weight
- Average: 155.1943
Monoisotopic: 155.094628665 - Chemical Formula
- C8H13NO2
- Synonyms
- Not Available
Pharmacology
- Indication
- Not Available
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism UMuscarinic acetylcholine receptor M1 Not Available Humans UMuscarinic acetylcholine receptor M3 Not Available Humans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAcebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Arecoline. Ambenonium The risk or severity of adverse effects can be increased when Ambenonium is combined with Arecoline. Amikacin The therapeutic efficacy of Arecoline can be decreased when used in combination with Amikacin. Aprotinin The risk or severity of adverse effects can be increased when Aprotinin is combined with Arecoline. Atenolol The risk or severity of adverse effects can be increased when Atenolol is combined with Arecoline. Betaxolol The risk or severity of adverse effects can be increased when Betaxolol is combined with Arecoline. Bisoprolol The risk or severity of adverse effects can be increased when Bisoprolol is combined with Arecoline. Capreomycin The therapeutic efficacy of Arecoline can be decreased when used in combination with Capreomycin. Capsaicin The risk or severity of adverse effects can be increased when Capsaicin is combined with Arecoline. Carvedilol The risk or severity of adverse effects can be increased when Carvedilol is combined with Arecoline. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Arecoline hydrobromide 24S79B9CX7 300-08-3 AXOJRQLKMVSHHZ-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Not Available
- Sub Class
- Not Available
- Direct Parent
- Alkaloids and derivatives
- Alternative Parents
- Hydropyridines / Methyl esters / Enoate esters / Trialkylamines / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Aliphatic heteromonocyclic compound / Alkaloid or derivatives / Alpha,beta-unsaturated carboxylic ester / Amine / Amino acid or derivatives / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Enoate ester show 13 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- methyl ester, enoate ester, tetrahydropyridine, pyridine alkaloid (CHEBI:2814) / Pyridine alkaloids (C10129)
Chemical Identifiers
- UNII
- 4ALN5933BH
- CAS number
- 63-75-2
- InChI Key
- HJJPJSXJAXAIPN-UHFFFAOYSA-N
- InChI
- InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
- IUPAC Name
- methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
- SMILES
- COC(=O)C1=CCCN(C)C1
References
- Synthesis Reference
K. S. Keshave Murthy, Allan W. Rey, Dan S. Matu, "Preparation of 1,2,5,6-tetra-hydro-3-carboalkoxypridines such as arecoline and salts of 1,2,5,6-tetrahydro-3-carboalkoxypridines and arecoline hydrobromide." U.S. Patent US6132286, issued October 17, 2000.
US6132286- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0030353
- KEGG Compound
- C10129
- PubChem Compound
- 2230
- PubChem Substance
- 46507231
- ChemSpider
- 13872064
- BindingDB
- 46858
- ChEBI
- 2814
- ChEMBL
- CHEMBL7303
- ZINC
- ZINC000052541469
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Arecoline
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) < 25 °C PhysProp boiling point (°C) 209 °C PhysProp water solubility 1E+006 mg/L (at 25 °C) MERCK INDEX (1996) logP 0.35 HANSCH,C ET AL. (1995) logS 0.81 ADME Research, USCD pKa 7.16 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 446.0 mg/mL ALOGPS logP 0.55 ALOGPS logP 0.65 ChemAxon logS 0.46 ALOGPS pKa (Strongest Basic) 8.23 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 29.54 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 43.86 m3·mol-1 ChemAxon Polarizability 17.1 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9713 Blood Brain Barrier + 0.9613 Caco-2 permeable + 0.6557 P-glycoprotein substrate Substrate 0.6628 P-glycoprotein inhibitor I Non-inhibitor 0.6202 P-glycoprotein inhibitor II Non-inhibitor 0.9697 Renal organic cation transporter Inhibitor 0.6075 CYP450 2C9 substrate Non-substrate 0.8958 CYP450 2D6 substrate Substrate 0.5321 CYP450 3A4 substrate Substrate 0.5051 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9061 CYP450 3A4 inhibitor Non-inhibitor 0.982 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9564 Ames test AMES toxic 0.9107 Carcinogenicity Non-carcinogens 0.8927 Biodegradation Ready biodegradable 0.9234 Rat acute toxicity 1.8241 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.5396 hERG inhibition (predictor II) Non-inhibitor 0.8535
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-0006-9400000000-c2ac70d939302e3f979b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM3
- Uniprot ID
- P20309
- Uniprot Name
- Muscarinic acetylcholine receptor M3
- Molecular Weight
- 66127.445 Da
References
- Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [PubMed:9224827]
Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:52
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