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Details

Stereochemistry ACHIRAL
Molecular Formula C8H13NO2
Molecular Weight 155.1943
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARECOLINE

SMILES

COC(=O)C1=CCCN(C)C1

InChI

InChIKey=HJJPJSXJAXAIPN-UHFFFAOYSA-N
InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3

HIDE SMILES / InChI
Arecoline is a natural alkaloid and is an effective constituent of Areca catechu L. (Arecaceae) with various pharmacological activities including effects on nervous, cardiovascular, digestive and endocrine systems and anti-parasitic effects. Antinociception of arecoline is mediated by the activation of the muscarinic acetylcholine receptors. It was found that this compound leads to oral submucosal fibrosis and oral cancer. Lung cancer is a severe type of carcinoma with high cell motility that is difficult to treat. As a result, further studies are needed to reduce or eliminate the toxicity of the compound before developing into a new drug.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Proceedings: On the central action of nomifensine (author's transl)].
1976
Effect of muscarinic cholinergic drugs on morphine-induced catalepsy, antinociception and changes in brain dopamine metabolism.
1977 Mar 23
Evidence that a nigral gabaergic--cholinergic balance controls posture.
1979 Jan 1
Anti-tremor action of C10Dichol, a peripheral acetylcholine synthesis inhibitor.
1980
Modification of cholinergic tremor by apomorphine and L-dopa in rats.
1980 Nov-Dec
[Modification, by lithium, of catalepsy induced by central cholinergic stimulants and morphine-like drugs].
1981
Physostigmine and arecoline: effects of intravenous infusions in Alzheimer presenile dementia.
1981 Jan
The effects of organophosphate-induced cholinergic stimulation on the antibody response to sheep erythrocytes in inbred mice.
1983 Apr
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.
1983 Jan
Effects of dopamine agonists, catecholamine depletors, and cholinergic and GABAergic drugs on acute dyskinesias in squirrel monkeys.
1984
Screening for new compounds with antiherpes activity.
1984 Oct
Subclassification of muscarinic receptors in the heart, urinary bladder and sympathetic ganglia in the pithed rat. Selectivity of some classical agonists.
1985 Dec
Ethanol withdrawal tremor does not interact with physostigmine-induced tremor in rat.
1985 Sep
Status epilepticus is produced by administration of cholinergic agonists to lithium-treated rats: comparison with kainic acid.
1987 Dec
Effects of nootropic drugs in a scopolamine-induced amnesia model in mice.
1988
Alleviation of scopolamine amnesia by different retrieval enhancing treatments.
1988 Aug
Amelioration of experimental amnesia (passive avoidance failure) in rodents by the selective M1 agonist AF102B.
1988 Dec
[Nonuniform expression of the dopamine-positive effect in different central m-cholinergic blockaders].
1988 Mar-Apr
Pharmacological characterization of the M1 muscarinic receptors expressed in murine fibroblast B82 cells.
1989 Feb
Effects of N-(2,6-dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide (DM-9384) on learning and memory in rats.
1989 May
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
[The possible role of presynaptic effects in realizing the protective action of M-cholinolytics in dimethyl dichlorovinyl phosphate poisoning].
1991 Jul-Aug
Intrathecal cholinergic agonists lessen bupivacaine spinal-block-induced hypotension in rats.
1994 Jul
[The selectivity of the action of muscarinic agonists in vivo].
1994 Mar-Apr
Pharmacological activity and receptor-binding characteristics of 2 beta-(2'-phenyl-2'-cyclopentyl-2'-hydroxy-ethoxy)tropane and its optical isomers.
1996 Mar-Apr
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
1997 Jul
Anticholinergic activity in mice and receptor-binding properties in rats of a series of synthetic tropane derivatives.
1997 Mar
Anti-nicotinic properties of anticholinergic antiparkinson drugs.
1998 Nov
Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor.
2000 Mar 31
M1 receptor activation is a requirement for arecoline analgesia.
2001 May-Jul
High-performance liquid chromatographic determination of arecoline in human saliva.
2004 Apr 2
Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits.
2004 Jun 30
Oral submucous fibrosis: review on aetiology and pathogenesis.
2006 Jul
Arecoline inhibits the 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced cytochrome P450 1A1 activation in human hepatoma cells.
2007 Jul 19
Characterization of arecoline-induced effects on cytotoxicity in normal human gingival fibroblasts by global gene expression profiling.
2007 Nov
Differential effect of arecoline on the endogenous dioxin-responsive cytochrome P450 1A1 and on a stably transfected dioxin-responsive element-driven reporter in human hepatoma cells.
2007 Oct 1
Synthesis of Novel 3-Aryl-N-Methyl-1,2,5,6-Tetrahydropyridine Derivatives by Suzuki coupling: As Acetyl Cholinesterase Inhibitors.
2007 Sep 5
The upregulation of metallothionein-1 expression in areca quid chewing-associated oral squamous cell carcinomas.
2008 Feb
[The characterization of central neuromediation in rats fed with magnesium-deprived diet before and after magnesium replenishment].
2008 Jul
Co-treating with arecoline and 4-nitroquinoline 1-oxide to establish a mouse model mimicking oral tumorigenesis.
2010 Jan 5
Effects of arecoline on adipogenesis, lipolysis, and glucose uptake of adipocytes-A possible role of betel-quid chewing in metabolic syndrome.
2010 Jun 15
Interaction of phytochemicals with hypoglycemic drugs on glucose uptake in L6 myotubes.
2011 Feb 15
Bronchial epithelium-derived IL-8 and RANTES increased bronchial smooth muscle cell migration and proliferation by Krüppel-like factor 5 in areca nut-mediated airway remodeling.
2011 May
Areca nut induces miR-23a and inhibits repair of DNA double-strand breaks by targeting FANCG.
2011 Oct
Arecoline augments cellular proliferation in the prostate gland of male Wistar rats.
2011 Sep 1
Arecoline decreases interleukin-6 production and induces apoptosis and cell cycle arrest in human basal cell carcinoma cells.
2012 Jan 15
Arecoline inhibits and destabilizes agrin-induced acetylcholine receptor cluster formation in C2C12 myotubes.
2013 Oct
Effects of arecoline on hepatic cytochrome P450 activity and oxidative stress.
2014 Aug
Helioxanthin suppresses the cross talk of COX-2/PGE2 and EGFR/ERK pathway to inhibit Arecoline-induced Oral Cancer Cell (T28) proliferation and blocks tumor growth in xenografted nude mice.
2016 Dec
Role of autophagy induced by arecoline in angiogenesis of oral submucous fibrosis.
2019 Jun
Patents

Sample Use Guides

different concentrations of Arecoline treatment (10 µM, 20 µM, and 40 µM) significantly increased the cell migration ability in A549 and CL1-0 cells and promoted the formation of the filamentous actin (F-actin) cytoskeleton, which is a crucial element for cell migration.
Name Type Language
ARECOLINE
MI  
Common Name English
NSC-56321
Code English
ARECOLINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47796
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
Code System Code Type Description
DRUG BANK
DB04365
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY
CAS
63-75-2
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID3022617
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY
NSC
56321
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY
NCI_THESAURUS
C76610
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY
FDA UNII
4ALN5933BH
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY
MERCK INDEX
m2038
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
200-565-5
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY
MESH
D001115
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY
WIKIPEDIA
Arecoline
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY
PUBCHEM
2230
Created by admin on Fri Dec 15 15:06:05 GMT 2023 , Edited by admin on Fri Dec 15 15:06:05 GMT 2023
PRIMARY