Arecoline

Base Information

• Chemical Name: Arecoline
• CAS No.: 63-75-2
• Molecular Formula: C8H13 N O2
• Molecular Weight: 155.197
• European Community (EC) Number: 200-565-5
• NSC Number: 56321
• UNII: 4ALN5933BH
• DSSTox Substance ID: DTXSID3022617
• Nikkaji Number: J4.830E
• Wikipedia: Arecoline
• Wikidata: Q423515
• NCI Thesaurus Code: C76610
• Pharos Ligand ID: 5H1ZU28KS7R3
• Metabolomics Workbench ID: 44346
• ChEMBL ID: CHEMBL7303
• Mol file: 63-75-2.mol

Synonyms:Arecaline;Arecholin;Arecholine;Arecolin;Arecoline;Methylarecaidin

Chemical Property of Arecoline

Chemical Property:

• Appearance/Colour: Yellow Oil
• Vapor Pressure: 0.208mmHg at 25°C
• Melting Point: <25 oC
• Refractive Index: 1.483
• Boiling Point: 209°Cat760mmHg
• PKA: 6.84(at 25℃)
• Flash Point: 81.1°C
• Density: 1.059g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 155.094628657
• Heavy Atom Count: 11
• Complexity: 187

Purity/Quality:

99% ^*data from raw suppliers

Arecoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC=C(C1)C(=O)OC
• Description: Areca catechu L. (Bin Lang), a palm plant native to Malaysia, is mainly distributed in tropical regions of Asia and the Americas. Arecoline is extracted from dry mature seeds of areca. The mature seeds of areca are 3–5 cm in diameter, with fibrous peel and a seed, namely, areca nut. The endosperm of areca nut is hard, with grayish-brown spots. Areca nut is harvested from August to November every year before the fruit is fully mature. The seeds are peeled, boiled, and cut into thin slices. The dried slices are brown or black, and it is an important medicine in traditional Chinese medicine. Areca nut is the raw materials of catechu. Areca nut was used as anthelmintics with arecoline as the main alkaloid in it.
• Physical properties: Appearance: oily liquid. Solubility: mixed with water, ethanol, or ether in any ratio, soluble in chloroform. Density: 1.059?g/cm3 . Boiling point (760?mmHg): 209?°C. Flash point: 81.1?°C. Vapor pressure (25?°C): 0.208?mmHg. Arecoline can be synthesized to salts with organic acids. Arecoline hydrobromide, arecoline acetarsol, and arecoline p-antimony carboxybenzoic acid are commonly used.
• Uses: A cholinergic alkaloid from seeds of the betel nut palm Areca catechu. Anthelmintic (Cestodes); cathartic Arecoline has shown regulatory properties of controlling plasminogen activator inhibitor-1 expression in human buccal mucosa fibroblasts.
• Indications: This product has no source standard. Tablets: anthelmintics, less used now. Eye drops: cholinergic drugs for glaucoma treatment.
• Clinical Use: Arecoline is of historical interest, because its structure, like those of many other early medicinal agents, was determined and confirmed by a 19th-century German pharmacist, E. Jahns. Xanomeline may be viewed as a nonclassical bio-isostere of the ester moiety of arecoline. It is a muscarinic M1/M4 agonist that is showing promise in clinical trials for the treatment of Alzheimer's disease. Although it is not tolerated at orally effective doses, transdermal delivery systems are showing promise.

Technology Process of Arecoline

There total 17 articles about Arecoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

arecoline hydrobromide (300-08-3) → arecoline (63-75-2)

Guidance literature:

With potassium carbonate; In dichloromethane; water; at 20 ℃; for 0.5h;

Reference yield: 88.88%

N-Methyl-3-carbomethoxy-4-hydroxypiperidine (86343-57-9) → arecoline (63-75-2)

Guidance literature:

With sodium methylate; In methanol; for 6.5h; Time; Reflux;

Reference yield: 29.3%

nicotinic acid (59-67-6) + methyl iodide (74-88-4) → arecoline (63-75-2)

Guidance literature:

nicotinic acid; methyl iodide; With triethylamine; In toluene; at 50 ℃; for 3h;

With sodium tris(acetoxy)borohydride; In toluene; at 20 - 38 ℃; for 5h;

upstream raw materials:

1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid

3-cyano-1-methyl-1,2,5,6-tetrahydropyridine

3-(methoxycarbonyl)-1-methylpyridinium iodide

oxalic acid

Downstream raw materials:

1-Methyl-3-diphenylmethyl-piperidein-(3)

1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid

1-methyl-1,2,5,6-tetrahydropyridine-3-carboxamide

4-amino-1-methyl-piperidine-3-carboxylic acid amide

Refernces

• 1、 -. "Synthetic method of arecoline". Paragraph 0032; 0042-0045; 0052-0053. . Retrieved 2021/04/26.
• 2、 Long, Sha,Stefani, Francesca Romana,Biondi, Stefano,Ghiselli, Giancarlo,Panunzio, Mauro. "N-Heteroarylmethyl-5-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylic acid a novel scaffold for the design of uncompetitive α-glucosidase inhibitors". . p. 5811 - 5822. Retrieved 2013/09/12.