| Identification | More | [Name]
Arecoline hydrobromide | [CAS]
300-08-3 | [Synonyms]
1-METHYL-1,2,5,6-TETRAHYDRO-3-PYRIDINECARBOXYLIC ACID METHYL ESTER HYDROBROMIDE
ARECAIDINE METHYL ESTER HYDROBROMIDE
ARECOLINE
ARECOLINE HBR
ARECOLINE HYDROBROMIDE
ARECOLINIUM BROMIDE
METHYL 1,2,5,6-TETRAHYDRO-1-METHYL-3-PYRIDINECARBOXYLATE HYDROBROMIDE
METHYL 1,2,5,6-TETRAHYDRO-1-METHYLNICOTINATE HYDROBROMIDE
METHYL 1-METHYL-1,2,5,6-TETRAHYDRONICOTINATE HYDROBROMIDE
METHYL 1-METHYL-1,2,5,6-TETRAHYDROPYRIDINE-3-CARBOXYLATE HYDROBROMIDE
arecolinebromide
arekolinhydrobromid
methyl-1,2,5,6-tetrahydro-1-methyl
nicotinicacid,1,2,5,6-tetrahydro-1-methyl-,methylester,hydrobromide
n-methyltetrahydronicotinicacidmethylesterhydrobromide
arecane
ARECOLINE HYDROBROMIDE CHOLINERGIC AGONI ST
ARECOLIN HYDROBROMIDE VETRANAL, 250
ARECOLINE HYDROBROMIDE CRYSTALLINE
Arecoline hydrobromide, 99+% | [EINECS(EC#)]
206-087-3 | [Molecular Formula]
C8H14BrNO2 | [MDL Number]
MFCD00039041 | [Molecular Weight]
236.11 | [MOL File]
300-08-3.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE FINE POWDER | [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 | [Detection Methods]
T,NMR | [Merck ]
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) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
300-08-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,T | [Risk Statements ]
R22:Harmful if swallowed.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S38:In case of insufficient ventilation, wear suitable respiratory equipment .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [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 |
| Questions And Answer | Back Directory | [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]
- https://www.sigmaaldrich.com/catalog/product/sial/31593?lang=en®ion=US
- Batham, E. J. "Testing arecoline hydrobromide as an anthelminthic for hydatid worms in dogs." Parasitology 37.3-4(1946):185.
- https://www.ncbi.nlm.nih.gov/pubmed/4544776
- ZHOU. "Security of a Novel Antitapeworm Drug: Arecoline Hydrobromide." Animal Husbandry and Feed Science 2(2010):26-28.
|
| Hazard Information | Back Directory | [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]. | [storage]
Store at -20°C |
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