arecoline

methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate

CAS: 63-75-2 C8 H13 N O2 MW: 155.19701000

Identification

Namearecoline
IUPACmethyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
CAS Number63-75-2
EINECS200-565-5
FDA UNII4ALN5933BH
Molecular FormulaC8 H13 N O2
Molecular Weight155.19701000
MDL NumberMFCD00059167
Nikkaji NumberJ4.830E
Beilstein0123045
XlogP30.30 (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 Toxicityunreported-dog LDLo 5 mg/kg
Dermal Toxicitysubcutaneous-dog LD50 5 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for arecoline usage levels up tonot for fragrance use.
Recommendation for arecoline flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

areca catechu areca catechu seed

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.