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
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
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 |
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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Effects of dopamine agonists, catecholamine depletors, and cholinergic and GABAergic drugs on acute dyskinesias in squirrel monkeys. | 1984 |
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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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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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[Nonuniform expression of the dopamine-positive effect in different central m-cholinergic blockaders]. | 1988 Mar-Apr |
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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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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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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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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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Arecoline augments cellular proliferation in the prostate gland of male Wistar rats. | 2011 Sep 1 |
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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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:06:05 GMT 2023
by
admin
on
Fri Dec 15 15:06:05 GMT 2023
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Record UNII |
4ALN5933BH
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Record Status |
Validated (UNII)
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Record Version |
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C47796
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DB04365
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63-75-2
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C76610
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m2038
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D001115
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Arecoline
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |