Arecoline hydrobromide

Arecoline hydrobromide Basic information
Description References
Product Name:Arecoline hydrobromide
Synonyms:arecolinebromide;arekolinhydrobromid;arecane;ARECOLINE HYDROBROMIDE CHOLINERGIC AGONI ST;ARECOLIN HYDROBROMIDE VETRANAL, 250;ARECOLINE HYDROBROMIDE CRYSTALLINE;Arecoline hydrobromide, 99+%;3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester, hydrobromide
CAS:300-08-3
MF:C8H14BrNO2
MW:236.11
EINECS:206-087-3
Product Categories:Intermediates & Fine Chemicals;Neurochemicals;Pyridine Alkaloids;Alkaloids;Biochemistry;Pharmaceuticals;Heterocyclic Compounds;Esters;Pyridines;Inhibitors
Mol File:300-08-3.mol
Arecoline hydrobromide Structure
Arecoline hydrobromide Chemical Properties
Melting point 171-175 °C
storage temp. Inert atmosphere,Room Temperature
solubility H2O: 0.1 g/mL, clear, colorless
pka6.84(at 25℃)
form Powder
color White to light yellow
Merck 14,778
BRN 3914826
Stability:Stable for 2 years from date of purchase as supplied. Solutions are not stable – make fresh daily.
InChIKeyAXOJRQLKMVSHHZ-UHFFFAOYSA-N
CAS DataBase Reference300-08-3(CAS DataBase Reference)
EPA Substance Registry SystemArecoline hydrobromide (300-08-3)
Safety Information
Hazard Codes Xn,T
Risk Statements 22-23/24/25
Safety Statements 45-38-36/37/39-28A
RIDADR 1544
WGK Germany 3
RTECS QT2275000
8
HazardClass 6.1
PackingGroup III
HS Code 29399990
ToxicityLD50 par-rat: 270 mg/kg ABMGAJ 28,681,72
MSDS Information
Arecoline hydrobromide Usage And Synthesis
DescriptionArecoline 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.
References
  1. https://www.sigmaaldrich.com/catalog/product/sial/31593?lang=en&region=US
  2. Batham, E. J. "Testing arecoline hydrobromide as an anthelminthic for hydatid worms in dogs." Parasitology 37.3-4(1946):185.
  3. https://www.ncbi.nlm.nih.gov/pubmed/4544776
  4. ZHOU. "Security of a Novel Antitapeworm Drug: Arecoline Hydrobromide." Animal Husbandry and Feed Science 2(2010):26-28.
DescriptionArecoline (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
Chemical PropertiesWHITE FINE POWDER
UsesArecoline 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
UsesA cholinergic alkaloid from seeds of the betel nut palm Areca catechu. Anthelmintic (Cestodes); cathartic.
General DescriptionArecoline is an alkaloid obtained from theseeds of the betel nut (Areca catechu). For many years, nativesof the East Indies have consumed the betel nut as asource of a euphoria-creating substance.
Safety ProfilePoison by parenteral,subcutaneous, and intravenous routes. When heated todecomposition it emits very toxic fumes of HBr and NOx.
References1) Fan?et al.?(2016),?Tetrameric Acetyl-CoA Acetyltransferase 1 is Important for Tumor Growth; Mol. Cell,?64?859 2) Heinrich?et al.?(2009),?Pharmacological comparison of muscarinic ligands: historical versus more recent muscarinic M1-preferring receptor agonists; Eur. J. Pharmacol.,?605?53 3) Christie?et al.?(1981),?Physostigmine and arecoline: effects of intravenous infusions in Alzheimer presenile dementia; Br. J. Psychiatry,?138?46
Arecoline hydrobromide Preparation Products And Raw materials
Preparation Productsarecoline-->ARECAIDINE HYDROCHLORIDE
Methylparaben Paraquat dichloride Methyl Arecoline hydrobromide Pyridine hydrobromide Tetrahydro Acetonitrile 1,2,3,6-TETRAHYDROPYRIDINE DEXTROMETHORPHAN HYDROBROMIDE Basic Violet 1 Dextromethorphan hydrobromide monohydrate Kresoxim-methyl Hydrogen bromide HYOSCINE N BUTYL BROMIDE BP Methanol METHYL TRANS-2-METHYL-2-PENTENOATE Methyl acrylate Scopolamine hydrobromide

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