ARECOLINE

Investigational

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 Search

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

Molecular Formula	C8H13NO2
Molecular Weight	155.1943
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30951892 | https://www.ncbi.nlm.nih.gov/pubmed/30925742 | https://www.ncbi.nlm.nih.gov/pubmed/11482763

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

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M1 168 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19767446	Agonist 2752	7.0 nM [EC50]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056	Agonist 2752	95.0 nM [EC50]
Muscarinic acetylcholine receptor M3 160 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056	Agonist 2752	11.0 nM [EC50]
Muscarinic acetylcholine receptor M4 87 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056	Agonist 2752	0.41 µM [EC50]
Muscarinic acetylcholine receptor M5 63 Target ID: CHEMBL2035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056	Agonist 2752	69.0 nM [EC50]
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7783150 \| https://www.ncbi.nlm.nih.gov/pubmed/10857465 \| https://adisinsight.springer.com/drugs/800014145	Agonist 2752	73.0 nM [EC50]

PubMed

Title	Date	PubMed
Role of autophagy induced by arecoline in angiogenesis of oral submucous fibrosis.	2019-06	30951892
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.	2016-12	26464283
Effects of arecoline on hepatic cytochrome P450 activity and oxidative stress.	2014-08	25056785
Arecoline inhibits and destabilizes agrin-induced acetylcholine receptor cluster formation in C2C12 myotubes.	2013-10	23933062
Arecoline decreases interleukin-6 production and induces apoptosis and cell cycle arrest in human basal cell carcinoma cells.	2012-01-15	22108589
Areca nut induces miR-23a and inhibits repair of DNA double-strand breaks by targeting FANCG.	2011-10	21750350
Arecoline augments cellular proliferation in the prostate gland of male Wistar rats.	2011-09-01	21741983
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.	2011-05	21297082
Interaction of phytochemicals with hypoglycemic drugs on glucose uptake in L6 myotubes.	2011-02-15	20724125
Effects of arecoline on adipogenesis, lipolysis, and glucose uptake of adipocytes-A possible role of betel-quid chewing in metabolic syndrome.	2010-06-15	20406654
Co-treating with arecoline and 4-nitroquinoline 1-oxide to establish a mouse model mimicking oral tumorigenesis.	2010-01-05	19840781
[The characterization of central neuromediation in rats fed with magnesium-deprived diet before and after magnesium replenishment].	2008-07	18767395
The upregulation of metallothionein-1 expression in areca quid chewing-associated oral squamous cell carcinomas.	2008-02	17418620
Characterization of arecoline-induced effects on cytotoxicity in normal human gingival fibroblasts by global gene expression profiling.	2007-11	17682004
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.	2007-10-01	17707585
Synthesis of Novel 3-Aryl-N-Methyl-1,2,5,6-Tetrahydropyridine Derivatives by Suzuki coupling: As Acetyl Cholinesterase Inhibitors.	2007-09-05	19662135
Arecoline inhibits the 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced cytochrome P450 1A1 activation in human hepatoma cells.	2007-07-19	17234337
Oral submucous fibrosis: review on aetiology and pathogenesis.	2006-07	16311067
Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits.	2004-06-30	15481791
High-performance liquid chromatographic determination of arecoline in human saliva.	2004-04-02	15065782
M1 receptor activation is a requirement for arecoline analgesia.	2001-08-03	11482763
Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor.	2000-03-31	10857465
Anti-nicotinic properties of anticholinergic antiparkinson drugs.	1998-11	9877318
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.	1997-07	9224827
Anticholinergic activity in mice and receptor-binding properties in rats of a series of synthetic tropane derivatives.	1997-03	9231353
Pharmacological activity and receptor-binding characteristics of 2 beta-(2'-phenyl-2'-cyclopentyl-2'-hydroxy-ethoxy)tropane and its optical isomers.	1996-03-01	8937624
Intrathecal cholinergic agonists lessen bupivacaine spinal-block-induced hypotension in rats.	1994-07	8010419
[The selectivity of the action of muscarinic agonists in vivo].	1994-03-01	8205054
[The possible role of presynaptic effects in realizing the protective action of M-cholinolytics in dimethyl dichlorovinyl phosphate poisoning].	1991-07-01	1664807
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991-01-01	1710653
Effects of N-(2,6-dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide (DM-9384) on learning and memory in rats.	1989-05	2724699
Pharmacological characterization of the M1 muscarinic receptors expressed in murine fibroblast B82 cells.	1989-02	2537406
Amelioration of experimental amnesia (passive avoidance failure) in rodents by the selective M1 agonist AF102B.	1988-12	3244205
Alleviation of scopolamine amnesia by different retrieval enhancing treatments.	1988-08	3227033
[Nonuniform expression of the dopamine-positive effect in different central m-cholinergic blockaders].	1988-03-01	3378602
Effects of nootropic drugs in a scopolamine-induced amnesia model in mice.	1988	3137602
Status epilepticus is produced by administration of cholinergic agonists to lithium-treated rats: comparison with kainic acid.	1987-12	2824229
Subclassification of muscarinic receptors in the heart, urinary bladder and sympathetic ganglia in the pithed rat. Selectivity of some classical agonists.	1985-12	4094621
Ethanol withdrawal tremor does not interact with physostigmine-induced tremor in rat.	1985-09	4048228
Screening for new compounds with antiherpes activity.	1984-10	6517562
Effects of dopamine agonists, catecholamine depletors, and cholinergic and GABAergic drugs on acute dyskinesias in squirrel monkeys.	1984	6320248
The effects of organophosphate-induced cholinergic stimulation on the antibody response to sheep erythrocytes in inbred mice.	1983-04	6857660
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.	1983-01	6130710
Physostigmine and arecoline: effects of intravenous infusions in Alzheimer presenile dementia.	1981-01	7023592
[Modification, by lithium, of catalepsy induced by central cholinergic stimulants and morphine-like drugs].	1981	6268258
Modification of cholinergic tremor by apomorphine and L-dopa in rats.	1980-11-01	7246199
Anti-tremor action of C10Dichol, a peripheral acetylcholine synthesis inhibitor.	1980	6258692
Evidence that a nigral gabaergic--cholinergic balance controls posture.	1979-01-01	569589
Effect of muscarinic cholinergic drugs on morphine-induced catalepsy, antinociception and changes in brain dopamine metabolism.	1977-03-23	403561
[Proceedings: On the central action of nomifensine (author's transl)].	1976	989390

Patents

Sample Use Guides

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:29 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:29 GMT 2025`
Record UNII	4ALN5933BH
Record Status	`Validated (UNII)`
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Name

Type

Language

NSC-56321

Preferred Name

English

ARECOLINE

Common Name

English

ARECOLINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47796