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Arecoline hydrobromide

Description References

CAS No.300-08-3
Chemical Name:Arecoline hydrobromide
CBNumber:CB1250752
Molecular Formula:C8H14BrNO2
Formula Weight:236.11
MOL File:300-08-3.mol

Arecoline hydrobromide Property

Melting point 171-175 °C
storage temp. Inert atmosphere,Room Temperature
solubility H₂O: 0.1 g/mL, clear, colorless
form Powder
pka 6.84(at 25℃)
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.
InChI InChI=1S/C8H13NO2.BrH/c1-9-5-3-4-7(6-9)8(10)11-2;/h4H,3,5-6H2,1-2H3;1H
InChIKey AXOJRQLKMVSHHZ-UHFFFAOYSA-N
SMILES C1(C(=O)OC)=CCCN(C)C1.Br
CAS DataBase Reference 300-08-3(CAS DataBase Reference)
FDA UNII 24S79B9CX7
EPA Substance Registry System Arecoline hydrobromide (300-08-3)

Safety

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
F :8
HazardClass :6.1
PackingGroup :III
HS Code :29399990
Toxicity :LD50 par-rat: 270 mg/kg ABMGAJ 28,681,72

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302
Precautionary statements P264-P270-P301+P312-P501

Arecoline hydrobromide Price More Price(3)

Brand: Sigma-Aldrich(India)
Product number: 31593
Product name : Arecoline hydrobromide
Purity: VETRANAL?, analytical standard
Packaging: 250MG
Price: ₹5239.3
Updated: 2022/06/14
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Brand: ottokemi
Product number: A 2587
Product name : Arecoline hydrobromide, for HPLC >98%
Purity:
Packaging: 1gm
Price: ₹3249
Updated: 2022/05/26
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Brand: ottokemi
Product number: A 2587
Product name : Arecoline hydrobromide, for HPLC >98%
Purity:
Packaging: 5gm
Price: ₹8703
Updated: 2022/05/26
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Arecoline hydrobromide Chemical Properties,Usage,Production

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 anthelminthic^2-4. 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.
Description 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
Chemical Properties WHITE FINE POWDER
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
Uses A cholinergic alkaloid from seeds of the betel nut palm Areca catechu. Anthelmintic (Cestodes); cathartic.
Preparation According to a historical 1911 version of the German Pharmacopoeia, arecoline (as its hydrobromide; Arecoline hydrobromide) was produced from areca nuts using extraction with acidified water followed by several clean-up steps. The first industrial-scale extraction, reported in 1927, was based on the extraction of arecoline with diethyl ether. There are various approaches for the synthetic production of arecoline starting from nicotinic acid and iodomethane; methylamine hydrochloride, formaldehyde and acetaldehyde; or ethyl acrylate and methylamine. The most modern approach involves nicotinic acid methyl ester and methyl iodide.
Arecoline salts such as arecoline hydrochloride or arecoline hydrobromide may be obtained by dissolving arecoline in alcohol of low relative molecular mass (such as methanol, ethanol, isopropanol, butanol, or amyl alcohol) and adding sufficient amounts of acid (hydrochloric or bromic acid) to give a weakly acidic solution. The crystallized salts may be separated from the alcohol by filtration.
General Description Arecoline 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 Profile Poison by parenteral,subcutaneous, and intravenous routes. When heated todecomposition it emits very toxic fumes of HBr and NOx.
Toxicology Eighty rats were randomly divided into four groups: a high-dose group (1000 mg/kg), a medium-dose group (200 mg/kg), a low-dose group (100mg/kg), and a blank control group. The doses were administered daily via gastric lavage for 14 consecutive days. There were no significant differences in the low-dose Arecoline hydrobromide (Ah) group compared to the control group (P>0.05) with regard to body weight, organ coefficients, hematological parameters, and histopathological changes. In this study, the rats in the high-dose group exhibited clear inhibitory effects on blood biochemical parameters, including ALT, TP, and BUN levels. It was demonstrated that the toxicity reaction was intensified at the higher dosage, and clinical dosing should occur within a safe dosage range. With a continuous increase in the Ah dose, organ damage was aggravated, with different degrees of congestion, degeneration, and necrosis observed. The results accurately reflected the liver and kidney changes, whereas the results for the changes in the lung were poor. Hence, a long-term, continuous high dose of Ah was toxic[4].
References 1) 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
4) Xiaojuan Wei. “Evaluation of arecoline hydrobromide toxicity after a 14-day repeated oral administration in Wistar rats.” PLoS ONE (2015): e0120165.