All Photos(1)

10980

Sigma-Aldrich

Arecoline hydrobromide

≥99.0% (NT)

Synonym(s):
Methyl 1,2,5,6-tetrahydro-1-methyl-3-pyridinecarboxylate hydrobromide, 1-Methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester hydrobromide, Taeniolin, Arecaidine methyl ester hydrobromide, Methyl 1-methyl-1,2,5,6-tetrahydronicotinate hydrobromide
Empirical Formula (Hill Notation):
C8H13NO2 · HBr
CAS Number:
Molecular Weight:
236.11
Beilstein:
3914826
EC Number:
MDL number:
PubChem Substance ID:

assay

≥99.0% (NT)

mp

170-175 °C
172-176 °C (lit.)

solubility

H2O: 0.1 g/mL, clear, colorless

SMILES string

Br[H].COC(=O)C1=CCCN(C)C1

InChI

1S/C8H13NO2.BrH/c1-9-5-3-4-7(6-9)8(10)11-2;/h4H,3,5-6H2,1-2H3;1H

InChI key

AXOJRQLKMVSHHZ-UHFFFAOYSA-N

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Other Notes

Alkaloid from seeds of betel nut palm. Effect on human learning

Certificate of Analysis

Certificate of Origin

N Sitaram et al.
Science (New York, N.Y.), 201(4352), 274-276 (1978-07-21)
Arecholine (4 milligrams), a cholinergic agonist, and choline (10 grams), a precursor of acetylcholine, significantly enhanced serial learning in normal human subjects. The subjects received methscopolamine prior to both arecholine and placebo injections. Conversely, scopolamine (0.5 milligram), a cholinergic antagonist...
Adrian A Franke et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 80, 241-246 (2015-03-24)
Betel nut chewing causes cancer in humans, including strong associations with head and neck cancer in Guam. In the search for biomarkers of betel chewing we sought to identify chemicals specific for the 3 most commonly consumed betel preparations in...
Bing Li et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 969, 12-18 (2014-08-21)
A rapid and sensitive high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) method was developed and validated for the determination of arecoline concentration in dog plasma. Plasma sample was prepared by protein precipitation using n-hexane (containing 1% isoamyl alcohol) with β-pinene as...
Mafaz Ullah et al.
Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology, 43(10), 761-769 (2014-04-26)
Oral submucous fibrosis is a pre-malignant fibrotic condition caused by areca nut use and involves reduced mucosal vascularity. Arecoline is the principal areca nut alkaloid and is cytotoxic for epithelium and fibroblasts. Endothelial cell cycle arrest is reported on exposure...
Tzer-Min Kuo et al.
Journal of agricultural and food chemistry, 63(24), 5787-5794 (2015-06-11)
The metabolites of environmental chemicals play key roles in carcinogenesis. Areca nut is strongly associated with the development of oral potentially malignant disorders (OPMD) or cancer. The main alkaloid in the areca nut is arecoline, which is highly cytotoxic and...

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