arecoline
methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate
Identification
| Name | arecoline |
| IUPAC | methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate |
| CAS Number | 63-75-2 |
| EINECS | 200-565-5 |
| FDA UNII | 4ALN5933BH |
| Molecular Formula | C8 H13 N O2 |
| Molecular Weight | 155.19701000 |
| MDL Number | MFCD00059167 |
| Nikkaji Number | J4.830E |
| Beilstein | 0123045 |
| XlogP3 | 0.30 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 209.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.200000 mmHg @ 25.00 °C. (est) |
| Flash Point | 178.00 °F. TCC ( 81.10 °C. ) (est) |
| logP (o/w) | 0.350 |
| Soluble in | water, 1.00E+06 mg/L @ 25 °C (exp) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | unreported-dog LDLo 5 mg/kg |
| Dermal Toxicity | subcutaneous-dog LD50 5 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for arecoline usage levels up to | not for fragrance use. |
| Recommendation for arecoline flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
arecaidine methyl ester
arecaline
arecholin
arecholine
arecolin
arecoline base
arecoline1-methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate
methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
methyl 1,2,5,6-tetrahydro-1-methyl nicotinate
methyl 1,2,5,6-tetrahydro-1-methylnicotinate
methyl arecaiden
methyl methyl tetrahydronicotinate
methyl methyl-1,2,5,6-tetrahydronicotinate
methyl N-methyl tetrahydronicotinate
methyl N-methyl-1,2,5,6-tetrahydronicotinate
methyl N-methyltetrahydronicotinate
1-
methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
N-
methyl-d-tetrahydronicotinic acid methyl ester
1-
methyl-d(sup 3,4)tetrahydro-3-pyridinecarboxylate
1-
methyl-delta(sup 3,4)tetrahydro-3-pyridine carboxylate
methylarecaiden
methylarecaidin
methylarecaidine
N-
methyltetrahydronicotinic acid, methyl ester
nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester
3-
pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester
1,2,5,6-
tetrahydro-1-methyl-3-pyridine carboxylic acid methyl ester
1,2,5,6-
tetrahydro-1-methyl-3-pyridinecarboxylic acid methyl ester
1,2,5,6-
tetrahydro-1-methylnicotinic acid, methyl ester
PubMed:
Arecoline inhibits epithelial cell viability by upregulating the apoptosis pathway: implication for oral submucous fibrosis.
PubMed:
Arecoline inhibits and destabilizes agrin-induced acetylcholine receptor cluster formation in C2C12 myotubes.
PubMed:
Arecoline Alters Taste Bud Cell Morphology, Reduces Body Weight, and Induces Behavioral Preference Changes in Gustatory Discrimination in C57BL/6 Mice.
PubMed:
Fibrotic Effects of Arecoline N-Oxide in Oral Potentially Malignant Disorders.
PubMed:
Separation of polyphenols and arecoline from areca nut (Areca catechu L.) by solvent extraction, its antioxidant activity, and identification of polyphenols.
PubMed:
Arecoline inhibits myogenic differentiation of C2C12 myoblasts by reducing STAT3 phosphorylation.
PubMed:
Effect of arecoline on regeneration of injured peripheral nerves.
PubMed:
Arecoline N-oxide: its mutagenicity and possible role as ultimate carcinogen in areca oral carcinogenesis.
PubMed:
A preliminary report on the toxicity of arecoline on early pregnancy in mice.
PubMed:
[Determination of synephrine and arecoline contents in Xiao'er Xiaoji Zhike oral liquid].
PubMed:
Alkaloids from areca (betel) nuts and their effects on human sperm motility in vitro.
PubMed:
Cytotoxic and non-genotoxic effects of arecoline on human buccal fibroblasts in vitro.
PubMed:
Cytotoxic and cytostatic effects of arecoline and sodium nitrite on human cells in vitro.
PubMed:
Arecoline cytotoxicity on human oral mucosal fibroblasts related to cellular thiol and esterase activities.
PubMed:
Synthesis and muscarinic activity of a series of tertiary and quaternary N-substituted guvacine esters structurally related to arecoline and arecaidine propargyl ester.
PubMed:
Direct and translactational effect of arecoline alkaloid on the clocimum oil-modulated hepatic drug metabolizing enzymes in mice.
PubMed:
Gastric mucosal damage induced by arecoline seizure in rats.
PubMed:
Xenobiotic metabolism: a view through the metabolometer.
PubMed:
Lead-induced changes in muscarinic cholinergic sensitivity.
PubMed:
A review of the systemic adverse effects of areca nut or betel nut.
PubMed:
Composition of betel specific chemicals in saliva during betel chewing for the identification of biomarkers.
PubMed:
Effects of nicotinic and muscarinic compounds on biting attack in the cat.
PubMed:
Discriminative stimulus properties of muscarinic agonists.
PubMed:
[Advance in studies on areca nuts and their active substances].
PubMed:
[Effects of cholinergic drugs on delayed discrimination disruption by AF64A in rats].
PubMed:
Interactions between scopolamine and muscarinic cholinergic agonists or cholinesterase inhibitors on spatial alternation performance in rats.
PubMed:
Behavioural effects of the nicotinic agonists N-(3-pyridylmethyl)pyrrolidine and isoarecolone in rats.
PubMed:
Cholecystokinin receptors mediate enhanced memory retention produced by feeding and gastrointestinal peptides.
PubMed:
[Effect of central effective substances on alcohol preference].
PubMed:
New biological properties of coffee melanoidins.
PubMed:
Starvation activates MAP kinase through the muscarinic acetylcholine pathway in Caenorhabditis elegans pharynx.
PubMed:
Mapping out starvation responses.
PubMed:
Control of Echinococcus granulosus in Cyprus and comparison with other island models.
PubMed:
Central sites and mechanisms of action of nicotine.
PubMed:
Association constants of pyridine and piperidine alkaloids to amyloid beta peptide determined by electrochemical impedance spectroscopy.
PubMed:
Surface plasmon resonance based biosensors for exploring the influence of alkaloids on aggregation of amyloid-β peptide.
PubMed:
Characterization of the scopolamine stimulus in rats.
PubMed:
Effects of genetic mutations and chemical exposures on Caenorhabditis elegans feeding: evaluation of a novel, high-throughput screening assay.
PubMed:
Pharmacological characterization of the physostigmine stimulus in rats.
PubMed:
Discriminative stimulus properties of NIK-247 and tetrahydroaminoacridine, centrally active cholinesterase inhibitors, in rats.
PubMed:
Pharmacological specificity of N-methyl-D-aspartate discrimination in rats.
PubMed:
Possible serotonergic and dopaminergic mediation of the N-ethyl-3,4-methylenedioxyamphetamine discriminative stimulus.
PubMed:
Discriminative stimulus properties of physostigmine in rats.