Description References
ChemicalBook > CAS DataBase List > Arecoline hydrobromide

Arecoline hydrobromide

Description References
Product Name
Arecoline hydrobromide
CAS No.
300-08-3
Chemical Name
Arecoline hydrobromide
Synonyms
ArecoL;arecane;Taeniolin;ARECOLINE HBR;Arecoline hydr;arecolinebromide;ine hydrobromide;arekolinhydrobromid;ARECOLINIUM BROMIDE;Argatroban Anhydrous
CBNumber
CB1250752
Molecular Formula
C8H14BrNO2
Formula Weight
236.11
MOL File
300-08-3.mol
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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)
EPA Substance Registry System
Arecoline hydrobromide (300-08-3)
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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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
31593
Product name
Arecoline hydrobromide
Purity
VETRANAL
Packaging
250mg
Price
$58.5
Updated
2024/03/01
Cayman Chemical
Product number
13662
Product name
Arecoline (hydrobromide)
Purity
≥95%
Packaging
100mg
Price
$19
Updated
2024/03/01
Cayman Chemical
Product number
13662
Product name
Arecoline (hydrobromide)
Purity
≥95%
Packaging
250mg
Price
$41
Updated
2024/03/01
Cayman Chemical
Product number
13662
Product name
Arecoline (hydrobromide)
Purity
≥95%
Packaging
500mg
Price
$78
Updated
2024/03/01
TRC
Product number
A767500
Product name
Arecoline hydrobromide
Packaging
10mg
Price
$45
Updated
2021/12/16
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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 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.

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

A cholinergic alkaloid from seeds of the betel nut palm Areca catechu. Anthelmintic (Cestodes); cathartic.

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

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.

Arecoline hydrobromide Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Arecoline hydrobromide manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Arecoline hydrobromide 300-08-3
Price
US $500.00-300.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-23
Dorne Chemical Technology co. LTD
Product
Arecoline hydrobromide 300-08-3
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
100kg
Release date
2024-06-27
Hebei Zhuanglai Chemical Trading Co Ltd
Product
Arecoline hydrobromide 300-08-3
Price
US $79.00-38.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-11-19

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