ARECOLINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H13NO2.ClH
Molecular Weight	191.655
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=LQSWCSYIDIBGRR-UHFFFAOYSA-N

InChI=1S/C8H13NO2.ClH/c1-9-5-3-4-7(6-9)8(10)11-2;/h4H,3,5-6H2,1-2H3;1H

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

Molecular Formula	ClH
Molecular Weight	36.461
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 169 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19767446	Agonist 2678	7.0 nM [EC50]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056	Agonist 2678	95.0 nM [EC50]
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056	Agonist 2678	11.0 nM [EC50]
Muscarinic acetylcholine receptor M4 86 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056	Agonist 2678	0.41 µM [EC50]
Muscarinic acetylcholine receptor M5 62 Target ID: CHEMBL2035 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168056	Agonist 2678	69.0 nM [EC50]
Muscarinic acetylcholine receptor 160 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 2678	73.0 nM [EC50]

PubMed

Title	Date	PubMed
[Modification, by lithium, of catalepsy induced by central cholinergic stimulants and morphine-like drugs].	1981	6268258
The effects of organophosphate-induced cholinergic stimulation on the antibody response to sheep erythrocytes in inbred mice.	1983 Apr	6857660
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Ethanol withdrawal tremor does not interact with physostigmine-induced tremor in rat.	1985 Sep	4048228
Effects of nootropic drugs in a scopolamine-induced amnesia model in mice.	1988	3137602
Effects of N-(2,6-dimethylphenyl)-2-(2-oxo-1-pyrrolidinyl)acetamide (DM-9384) on learning and memory in rats.	1989 May	2724699
[The selectivity and protective properties of m-cholinolytics in dichlorodivinylphosphate poisoning].	1992 May-Jun	1458168
Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor.	2000 Mar 31	10857465
High-performance liquid chromatographic determination of arecoline in human saliva.	2004 Apr 2	15065782
Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits.	2004 Jun 30	15481791
Arecoline inhibits the 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced cytochrome P450 1A1 activation in human hepatoma cells.	2007 Jul 19	17234337
Co-treating with arecoline and 4-nitroquinoline 1-oxide to establish a mouse model mimicking oral tumorigenesis.	2010 Jan 5	19840781
Effects of arecoline on adipogenesis, lipolysis, and glucose uptake of adipocytes-A possible role of betel-quid chewing in metabolic syndrome.	2010 Jun 15	20406654
Interaction of phytochemicals with hypoglycemic drugs on glucose uptake in L6 myotubes.	2011 Feb 15	20724125
Areca nut induces miR-23a and inhibits repair of DNA double-strand breaks by targeting FANCG.	2011 Oct	21750350
Effects of arecoline on hepatic cytochrome P450 activity and oxidative stress.	2014 Aug	25056785
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	26464283
Role of autophagy induced by arecoline in angiogenesis of oral submucous fibrosis.	2019 Jun	30951892

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 `Fri Dec 15 19:13:20 GMT 2023` Edited by `admin` on `Fri Dec 15 19:13:20 GMT 2023`
Record UNII	9F5CR33W64
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARECOLINE HYDROCHLORIDE

Common Name

English

3-PYRIDINECARBOXYLIC ACID, 1,2,5,6-TETRAHYDRO-1-METHYL-, METHYL ESTER, HYDROCHLORIDE

Common Name

English

NSC-172133

Code

English

3-PYRIDINECARBOXYLIC ACID, 1,2,5,6-TETRAHYDRO-1-METHYL-, METHYL ESTER, HYDROCHLORIDE (1:1)

Common Name

English

NICOTINIC ACID, 1,2,5,6-TETRAHYDRO-1-METHYL-, METHYL ESTER, HYDROCHLORIDE

Common Name

English

ARECOLINE HCL

Common Name

English

Code System Code Type Description

PUBCHEM

6107