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arecoline

$156

  • Brand : BIOFRON

  • Catalogue Number : BD-D0911

  • Specification : HPLC≥98%

  • CAS number : 63-75-2

  • Formula : C8H13NO2

  • Molecular Weight : 155.19

  • PUBCHEM ID : 2230

  • Volume : 50mg

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Catalogue Number

BD-D0911

Analysis Method

Specification

HPLC≥98%

Storage

2-8°C

Molecular Weight

155.19

Appearance

Botanical Source

Structure Type

Category

SMILES

CN1CCC=C(C1)C(=O)OC

Synonyms

methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate/Arekolin/Arecolin/Arecholine/methyl N-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate/methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate/3-Methoxycarbonyl-1-methyl-1,2,5,6-tetrahydropyridine/Arecaline/Methylarecaiden/methyl 1,2,5,6-tetrahydro-1-methylnicotinate/Methylarecaidin/Arecoline base/Arecaidine methyl ester

IUPAC Name

methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate

Density

1.059g/cm3

Solubility

Flash Point

81.1ºC

Boiling Point

209ºC at 760mmHg

Melting Point

InChl

InChl Key

HJJPJSXJAXAIPN-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:63-75-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

27046150

Abstract

CONTEXT:
Arecoline is an effective constituent of Areca catechu L. (Arecaceae) with various pharmacological effects. However, investigations also revealed that long use of arecoline could arouse some oral diseases.

OBJECTIVE:
The present review gathers the fragmented information available in the literature (before 1 October 2015) regarding pharmacology and toxicology of arecoline. We also discussed the potential developments and applications of arecoline in the future.

METHODS:
All the available information regarding the arecoline is compiled from scientific databases, including Science Direct, PubMed, Web of Science, Scopus, etc.

RESULTS:
Previous research demonstrated that arecoline is one of the major effective constituents in A. catechu. Additionally, arecoline has a wide spectrum of pharmacological activities including effects on nervous, cardiovascular, digestive and endocrine systems and anti-parasitic effects. What’s more, arecoline is reported to be the primary toxic constituent of A. catechu, and the main toxic effects include oral submucous fibrosis (OSF), oral squamous cell carcinoma (OSCC) and genotoxicity.

CONCLUSION:
Arecoline has great potential to be a therapeutic drug for various ailments. However, further investigations are needed in the future to reduce or eliminate its toxicities before developing into new drug.

KEYWORDS

Alzheimer’s dementia; oral squamous cell carcinoma; oral submucous fibrosis

Title

The pharmacology, toxicology and potential applications of arecoline: a review.

Author

Liu YJ1, Peng W1, Hu MB1, Xu M1, Wu CJ1.

Publish date

2016 Nov

PMID

30011295

Abstract

The present study was designed to investigate the pathways involved in the effect of betel nut arecoline on cell viability in 3T3-L1 preadipocytes. Arecoline, but not arecaidine or guvacine, inhibited preadipocyte viability in a concentration- and time-dependent manner. Arecoline arrested preadipocyte growth in the G2/M phase of the cell cycle; decreased the total levels of cyclin-dependent kinase 1 (CDK1), p21, and p27 proteins; increased p53 and cyclin B1 protein levels; and had no effect on CDK2 protein levels. These results suggested that arecoline selectively affected a particular CDK subfamily. Arecoline inhibited AMP-activated protein kinase (AMPK) activity; conversely, the AMPK activator, AICAR, blocked the arecoline-induced inhibition of cell viability. Pre-treatment with the antioxidant, N-acetylcysteine, prevented the actions of arecoline on cell viability, G2/M growth arrest, reactive oxygen species (ROS) production, and the levels of CDK1, p21, p27, p53, cyclin B1, and phospho-AMPK proteins. These AMPK- and ROS-dependent effects of arecoline on preadipocyte growth may be related to the mechanism underlying the modulatory effect of arecoline on body weight.

Title

Arecoline inhibits the growth of 3T3-L1 preadipocytes via AMP-activated protein kinase and reactive oxygen species pathways.

Author

Tian ZH1, Weng JT1,2, Shih LJ3,4, Siao AC1, Chan TY1, Tsuei YW5, Kuo YC6, Wang TS7, Kao YH1.

Publish date

2018 Jul 16

PMID

32200293

Abstract

BACKGROUND:
Areca nut has anti-inflammatory, antiparasitic, antihypertensive, and antidepressant properties. The pathological hallmarks of inflammatory joint diseases are an increased number of osteoclasts and impaired differentiation of osteoblasts, which may disrupt the bone remodeling balance and eventually lead to bone loss.

PURPOSE:
The present study assessed the effects of arecoline, the main alkaloid found in areca nut, on osteoclast and osteoblast differentiation and function.

METHOD:
M-CSF/RANKL-stimulated murine bone marrow-derived macrophages (BMMs) were incubated with several concentrations of arecoline, and TRAP staining and pit formation were assessed to monitor osteoclast formation. Quantitative real-time RT-PCR and western blot analyses were used to analyze the expression of osteoclast-associated genes and signaling pathways. The effects of arecoline on bone were investigated in an in vivo mouse model of lipopolysaccharide (LPS)-induced trabecular bone loss after oral administration of arecoline. Alizarin red S staining and assays to measure ALP activity and the transcription level of osteoblast-related genes were used to evaluate the effects of arecoline on osteoblast differentiation and bone mineralization.

RESULTS:
In a dose-dependent manner, arecoline at concentrations of 50-100 μM reduced both the development of TRAP-positive multinucleated osteoclasts and the formation of resorption pits in M-CSF/RANKL-stimulated BMMs. In M-CSF/RANKL-stimulated BMMs, arecoline also suppressed the expression and translocation of c-Fos and NFATcl, and osteoclast differentiated-related genes via interference with the AKT, MAPK, and NF-kB activation pathways. Femur bone loss and microcomputed tomography parameters were recovered by oral administration of arecoline in the mouse LPS-induced bone loss model. Lastly, arecoline increased ALP activity, bone mineralization, and the expression of osteoblast differentiation-related genes, such as ALP and Runx2, in MC3T3-E1 cells.

CONCLUSION:
Our data suggest that arecoline may attenuate or prevent bone loss by suppressing osteoclastogenesis and promoting osteoblastogenesis. These findings provide evidence supporting arecoline’s use as a potential therapeutic agent in bone-loss disorders and diseases.

Copyright © 2020 Elsevier GmbH. All rights reserved.

KEYWORDS

Arecoline; Osteoblast; Osteoclast; RANKL

Title

Arecoline suppresses RANKL-induced osteoclast differentiation in vitro and attenuates LPS-induced bone loss in vivo.

Author

Liu FL1, Chen CL2, Lai CC3, Lee CC2, Chang DM4.

Publish date

2020 Feb 22


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