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A6134

Arecoline hydrobromide

Name: Arecoline hydrobromide
Brand: SIGMA

≥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

UNSPSC Code:

12352100

Beilstein/REAXYS Number:

3914826

MDL number:

MFCD00039041

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Properties

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)

Description

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.

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Storage Class

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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Arecoline via miniosmotic pump improves AF64A-impaired radial maze performance in rats: a possible model of Alzheimer's disease.

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

Cholinergic agents: effect of methyl substitution in a series of arecoline derivatives on binding to muscarinic acetylcholine receptors.

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

Arecoline cytotoxicity on human oral mucosal fibroblasts related to cellular thiol and esterase activities.

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

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