Arecoline hydrobromide

Base Information

• Chemical Name: Arecoline hydrobromide
• CAS No.: 300-08-3
• Molecular Formula: C8H14BrNO2
• Molecular Weight: 236.109
• Hs Code.: 29399990
• European Community (EC) Number: 206-087-3
• NSC Number: 757418,31750
• UNII: 24S79B9CX7
• DSSTox Substance ID: DTXSID9075379
• Wikidata: Q27253878
• NCI Thesaurus Code: C72704
• Pharos Ligand ID: 5H1ZU28KS7R3
• ChEMBL ID: CHEMBL449209
• Mol file: 300-08-3.mol

Synonyms:arecoline hydrobromide

Chemical Property of Arecoline hydrobromide

Chemical Property:

• Appearance/Colour: white fine powder
• Vapor Pressure: 0.208mmHg at 25°C
• Melting Point: 171-175 °C
• Boiling Point: 209 °C at 760 mmHg
• PKA: 6.84(at 25℃)
• Flash Point: 81.1 °C
• PSA: 29.54000
• LogP: 1.31730
• Storage Temp.: Refrigerator
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 235.02079
• Heavy Atom Count: 12
• Complexity: 187

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Arecoline hydrobromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T
• Statements: 22-23/24/25
• Safety Statements: 45-38-36/37/39-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCC=C(C1)C(=O)OC.Br
• Description: Arecoline hydrobromide is an arecoline salt of hydrobromic acid generally used in removing parasites from dog’s intestine1-2. It has been used for almost half a century for the treatment of Echinococcus granulosus in dogs, as an anthelminthic2-4. The vermifuge action of arecoline is due to a combination of factors, including (a) the increased activity of the intestinal glands, resulting in a copious secretion which may tend to loosen the hold of the worms on the mucous membrane, when (b) the increased peristalsis sweeps them onward to be voided with the faeces. It has a strong parasympathomimetic action4. It may have been used as working standard in the determination of arecoline concentration from dog plasma using LC–MS/MS1. Arecoline (CAS 300-8-3) is a covalent inhibitor of ACAT1 which binds to and disrupts only ACAT1 tetramers (IC50=11.1 μM). ACAT2 and DLAT are not inhibited. Tyrosine407 phosphorylation activates mitochondrial acetyl-CoA acetyltransferase 1 (ACAT1) by stabilizing its tetramer. This is believed to be the mechanisms by which ACAT1 is “hijacked” and contributes to the Warburg effect in cancer.? Treatment of xenograft nude mice with Arecoline resulted in a dose-dependent reduction in tumor mass.1?Agonist at muscarinic acetylcholine receptors M1 – M5 (EC50?in the range of 7-410 nM).2?May be effective in dementia.3
• Uses: Arecoline is a muscarinic acetylcholine receptor agonist. Arecoline induces ADP ribosylation of histones and chromatid relaxation in spleen and bone marrow cells. In a study, a controlled trial involving 122 dogs experimentally infected with Echinococcus A cholinergic alkaloid from seeds of the betel nut palm Areca catechu. Anthelmintic (Cestodes); cathartic.

Technology Process of Arecoline hydrobromide

There total 1 articles about Arecoline hydrobromide 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: 47.0%

→ arecoline hydrobromide (300-08-3)

Guidance literature:

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: 89.0%

arecoline hydrobromide (300-08-3) → 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (499-04-7)

Guidance literature:

arecoline hydrobromide; With sodium carbonate; In water; pH=10 - 11;

With water; Reflux;

DOI:10.1002/anie.201301341

Downstream raw materials:

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

1,1-Dimethyl-1,2,5,6-tetrahydro-nicotinsaeure-methylester-Iodid

arecoline

norarecoline

Refernces