Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H13NO2.BrH |
Molecular Weight | 236.106 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.COC(=O)C1=CCCN(C)C1
InChI
InChIKey=AXOJRQLKMVSHHZ-UHFFFAOYSA-N
InChI=1S/C8H13NO2.BrH/c1-9-5-3-4-7(6-9)8(10)11-2;/h4H,3,5-6H2,1-2H3;1H
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 | Condition | Potency |
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Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19767446 |
7.0 nM [EC50] | ||
Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056 |
95.0 nM [EC50] | ||
Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056 |
11.0 nM [EC50] | ||
Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056 |
0.41 µM [EC50] | ||
Target ID: CHEMBL2035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056 |
69.0 nM [EC50] | ||
73.0 nM [EC50] |
PubMed
Title | Date | PubMed |
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[Proceedings: On the central action of nomifensine (author's transl)]. | 1976 |
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Effect of muscarinic cholinergic drugs on morphine-induced catalepsy, antinociception and changes in brain dopamine metabolism. | 1977 Mar 23 |
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Evidence that a nigral gabaergic--cholinergic balance controls posture. | 1979 Jan 1 |
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Modification of cholinergic tremor by apomorphine and L-dopa in rats. | 1980 Nov-Dec |
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Physostigmine and arecoline: effects of intravenous infusions in Alzheimer presenile dementia. | 1981 Jan |
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The effects of organophosphate-induced cholinergic stimulation on the antibody response to sheep erythrocytes in inbred mice. | 1983 Apr |
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Ethanol withdrawal tremor does not interact with physostigmine-induced tremor in rat. | 1985 Sep |
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Status epilepticus is produced by administration of cholinergic agonists to lithium-treated rats: comparison with kainic acid. | 1987 Dec |
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Effects of nootropic drugs in a scopolamine-induced amnesia model in mice. | 1988 |
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Alleviation of scopolamine amnesia by different retrieval enhancing treatments. | 1988 Aug |
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Amelioration of experimental amnesia (passive avoidance failure) in rodents by the selective M1 agonist AF102B. | 1988 Dec |
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Effects of N-(2,6-dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide (DM-9384) on learning and memory in rats. | 1989 May |
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Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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[The possible role of presynaptic effects in realizing the protective action of M-cholinolytics in dimethyl dichlorovinyl phosphate poisoning]. | 1991 Jul-Aug |
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[The selectivity and protective properties of m-cholinolytics in dichlorodivinylphosphate poisoning]. | 1992 May-Jun |
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Intrathecal cholinergic agonists lessen bupivacaine spinal-block-induced hypotension in rats. | 1994 Jul |
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[The selectivity of the action of muscarinic agonists in vivo]. | 1994 Mar-Apr |
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Anti-nicotinic properties of anticholinergic antiparkinson drugs. | 1998 Nov |
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Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor. | 2000 Mar 31 |
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Effects of methyl mercury, mercuric sulfide and cinnabar on active avoidance responses, Na+/K+-ATPase activities and tissue mercury contents in rats. | 2001 Apr |
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M1 receptor activation is a requirement for arecoline analgesia. | 2001 May-Jul |
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High-performance liquid chromatographic determination of arecoline in human saliva. | 2004 Apr 2 |
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Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits. | 2004 Jun 30 |
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Oral submucous fibrosis: review on aetiology and pathogenesis. | 2006 Jul |
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Arecoline inhibits the 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced cytochrome P450 1A1 activation in human hepatoma cells. | 2007 Jul 19 |
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Characterization of arecoline-induced effects on cytotoxicity in normal human gingival fibroblasts by global gene expression profiling. | 2007 Nov |
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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 |
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Synthesis of Novel 3-Aryl-N-Methyl-1,2,5,6-Tetrahydropyridine Derivatives by Suzuki coupling: As Acetyl Cholinesterase Inhibitors. | 2007 Sep 5 |
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The upregulation of metallothionein-1 expression in areca quid chewing-associated oral squamous cell carcinomas. | 2008 Feb |
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[The characterization of central neuromediation in rats fed with magnesium-deprived diet before and after magnesium replenishment]. | 2008 Jul |
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Co-treating with arecoline and 4-nitroquinoline 1-oxide to establish a mouse model mimicking oral tumorigenesis. | 2010 Jan 5 |
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Effects of arecoline on adipogenesis, lipolysis, and glucose uptake of adipocytes-A possible role of betel-quid chewing in metabolic syndrome. | 2010 Jun 15 |
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Interaction of phytochemicals with hypoglycemic drugs on glucose uptake in L6 myotubes. | 2011 Feb 15 |
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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 |
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Areca nut induces miR-23a and inhibits repair of DNA double-strand breaks by targeting FANCG. | 2011 Oct |
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Arecoline augments cellular proliferation in the prostate gland of male Wistar rats. | 2011 Sep 1 |
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Arecoline decreases interleukin-6 production and induces apoptosis and cell cycle arrest in human basal cell carcinoma cells. | 2012 Jan 15 |
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Effects of arecoline on hepatic cytochrome P450 activity and oxidative stress. | 2014 Aug |
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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 |
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Role of autophagy induced by arecoline in angiogenesis of oral submucous fibrosis. | 2019 Jun |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30925742
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.
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NCI_THESAURUS |
C47796
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206-087-3
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300-08-3
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m2038
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CHEMBL7303
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C72704
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DBSALT002647
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24S79B9CX7
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DTXSID9075379
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD