EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

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

Supplier Sponsors

Name:methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
CAS Number: 63-75-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:200-565-5
FDA UNII: 4ALN5933BH
Nikkaji Web:J4.830E
Beilstein Number:0123045
MDL:MFCD00059167
XlogP3:0.30 (est)
Molecular Weight:155.19701000
Formula:C8 H13 N O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Arecoline > 95%
Odor: characteristic
Use: Arecoline has shown regulatory properties of controlling plasminogen activator inhibitor-1 expression in human buccal mucosa fibroblasts.
Santa Cruz Biotechnology
For experimental / research use only.
Arecoline
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
unreported-dog LDLo 5 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.

intraperitoneal-mouse LD50 190 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 192, Pg. 88, 1971.

intravenous-mouse LD50 36 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT
Farmakologiya i Toksikologiya Vol. 28, Pg. 33, 1965.

oral-mouse LD50 550 mg/kg
European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 26, Pg. 853, 1991.

unreported-mouse LDLo 100 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.

intraperitoneal-rat LD50 40 mg/kg
SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD VASCULAR: CONTRACTION (ISOLATED TISSUES)
Biochemical Journal. Vol. 113, Pg. 123, 1969.

oral-rat LD50 2500 mg/kg
European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 26, Pg. 853, 1991.

Dermal Toxicity:
subcutaneous-dog LD50 5 mg/kg
Fortschritte der Arzneimittelforschung. Progress in Drug Research. Vol. 17, Pg. 108, 1973.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :2230
National Institute of Allergy and Infectious Diseases:Data
methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
Chemidplus:0000063752
 
References:
 methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):2230
Pubchem (sid):134971811
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10129
HMDB (The Human Metabolome Database):HMDB30353
FooDB:FDB002198
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 areca catechu
Search Trop Picture
 areca catechu seed
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
an alkaloid obtained from the betel nut (areca catechu), fruit of a palm tree. it is an agonist at both muscarinic and nicotinic acetylcholine receptors. it is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. it has been used as a euphoriant in the pacific islands. Isol. from betel nuts Arecoline is an alkaloid natural product found in the areca nut, the fruit of the areca palm (Areca catechu). It is an oily liquid that is soluble in water, alcohols, and ether.; Owing to its muscarinic and nicotinic agonist properties, arecoline has shown improvement in the learning ability of healthy volunteers. Since one of the hallmarks of Alzheimer's disease is a cognitive decline, arecoline was suggested as a treatment to slow down this process and arecoline administered via i.v. route did indeed show modest verbal and spatial memory improvement in Alzheimer's patients, though due to arecoline's possible carcinogenic properties, it is not the first drug of choice for this degenerative disease.
Please share your Comments.
Email Address:
Top of Page Home
Copyright © 1980-2021 The Good Scents Company (tgsc) ™ Disclaimer Privacy Policy