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Merck
CN

10980

Arecoline hydrobromide

≥99.0% (NT)

Synonym(s):

1-Methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester hydrobromide, Arecaidine methyl ester hydrobromide, Methyl 1,2,5,6-tetrahydro-1-methyl-3-pyridinecarboxylate hydrobromide, Methyl 1-methyl-1,2,5,6-tetrahydronicotinate hydrobromide, Taeniolin

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About This Item

Empirical Formula (Hill Notation):
C8H13NO2 · HBr
CAS Number:
300-08-3
Molecular Weight:
236.11
EC Number:
206-087-3
UNSPSC Code:
12352100
PubChem Substance ID:
24846938
Beilstein/REAXYS Number:
3914826
MDL number:
MFCD00039041

Key Documents

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InChI key

AXOJRQLKMVSHHZ-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

≥99.0% (NT)

mp

170-175 °C, 172-176 °C (lit.)

solubility

H2O: 0.1 g/mL, clear, colorless

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Other Notes

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBB1194
1452839
1424446
1403667
1414271

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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
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
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
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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