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Safety Information

A6134

Sigma-Aldrich

Arecoline hydrobromide

≥98% (HPLC), powder

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
Beilstein:
3914826
MDL number:
MFCD00039041
UNSPSC Code:
12352100

Assay

≥98% (HPLC)

form

powder

color

white

mp

172-176 °C (lit.)

solubility

H2O: soluble (Solutions should be freshly prepared.)
ethanol: slightly soluble (Solutions should be freshly prepared.)

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

Gene Information

human ... CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133)

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Biochem/physiol Actions

Muscarinic acetylcholine receptor agonist. A constituent of betel nut that may be carcinogenic on prolonged exposure. Cytotoxicity is reduced by antioxidants, such as reduced glutathione or N-acetyl-L-cysteine. Induces ADP ribosylation of histones and chromatid relaxation in spleen and bone marrow cells.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

188.6 °F - Solvent

Flash Point(C)

87 °C - Solvent

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
015K1122
089F1044
089F0871
077H0896
063K3490

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A C Bartolomeo et al.
Neurobiology of learning and memory, 68(3), 333-342 (1997-12-17)
Male Sprague-Dawley rats, preoperatively trained in a 1-h delay non-match-to-position radial maze task, received bilateral stereotaxic injections of a selective cholinotoxin, ethylcholine aziridinium ion (AF64A: 3 nmol/3 microliters/lateral ventricle). Animals treated with AF64A made significantly more total postdelay errors than
J R Saikia et al.
Cancer letters, 139(1), 59-65 (1999-07-17)
Arecoline, the major alkaloid of betel nut (Areca catechu L.) and a suspected carcinogen, has been implicated in human cancers of various sites. A considerable portion of the world's population is constantly exposed to arecoline due to the habit of
J H Jeng et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 37(7), 751-756 (1999-09-25)
Betel quid (BQ) chewing is associated with an increased risk of oral submucous fibrosis (OSF) and oral cancer in India and many south-east Asian countries. Recently, we have shown that arecoline is cytotoxic to cultured human oral mucosal fibroblasts. This
W H Moos et al.
Journal of pharmaceutical sciences, 81(10), 1015-1019 (1992-10-01)
Arecoline, arecaidine, and a series of derivatives, differing by the presence or absence of methyl groups at positions on the periphery of the molecule, were prepared, and their binding to muscarinic acetylcholine receptors was tested. On the basis of this
A Chatterjee et al.
Cancer letters, 139(1), 23-31 (1999-07-17)
The carcinogenic potentiality of the major alkaloid of betel nut, arecoline (ARC), is well established. This study was undertaken to determine the differences in genotoxic effects of ARC when given by two different routes (oral administration (OA) and intraperitoneal injection

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