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
| Molecular Formula | BrH |
| Molecular Weight | 80.912 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| Effects of methyl mercury, mercuric sulfide and cinnabar on active avoidance responses, Na+/K+-ATPase activities and tissue mercury contents in rats. | 2001 Apr |
|
| M1 receptor activation is a requirement for arecoline analgesia. | 2001 May-Jul |
|
| 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 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:04:19 UTC 2023
by
admin
on
Fri Dec 15 15:04:19 UTC 2023
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| Record UNII |
24S79B9CX7
|
| Record Status |
Validated (UNII)
|
| Record Version |
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NCI_THESAURUS |
C47796
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206-087-3
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m2038
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PARENT -> SALT/SOLVATE |
