Arecaidine

CAS# 499-04-7

Arecaidine

Catalog No. BCN8282----Order now to get a substantial discount!

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Quality Control of Arecaidine

Number of papers citing our products

Chemical structure

Arecaidine

3D structure

Chemical Properties of Arecaidine

Cas No. 499-04-7 SDF Download SDF
PubChem ID 10355 Appearance Powder
Formula C7H11NO2 M.Wt 141.17
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 1-methyl-3,6-dihydro-2~{H}-pyridine-5-carboxylic acid
SMILES CN1CCC=C(C1)C(=O)O
Standard InChIKey DNJFTXKSFAMXQF-UHFFFAOYSA-N
Standard InChI InChI=1S/C7H11NO2/c1-8-4-2-3-6(5-8)7(9)10/h3H,2,4-5H2,1H3,(H,9,10)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Arecaidine

The fruits of Areca catechu

Biological Activity of Arecaidine

DescriptionArecaidine has tumorgenicity.
In vivo

Effects of the Areca nut constituents arecaidine and guvacine on the action of GABA in the cat central nervous system.[Pubmed: 922499 ]

Brain Res. 1977 Nov 18;136(3):513-22.

Arecaidine and guvacine, constituents of the nut of Areca catechu, inhibited the uptake of GABA and beta-alanine, but not that of glycine, by slices of cat spinal cord.
METHODS AND RESULTS:
In cats anesthetised with pentobarbitone, electrophoretic Arecaidine enhanced the inhibitory actions of GABA and beta-alanine, but not those of glycine or taurine, on the firing of spinal neurones. Similarly, electrophoretic guvacine enhanced the inhibition of spinal neurones by GABA but not that by glycine. The uptake of GABA by slices of cat cerebellum was inhibited by Arecaidine, and the effect of electrophoretic GABA on the firing of cerebellar Purkinje cells was enhanced by electrophoretic Arecaidine. When administered intravenously Arecaidine failed to affect synaptic inhibitions considered to be mediated by GABA. Intravenous Arecaidine had no effect on either spinal prolonged (presynaptic) inhibition (20mg/kg), dorsal root potentials (20mg/kg) or basket cell inhibition of Purkinje cells (250 mg/kg), although topical Arecaidine (6.6-10 x 10(-3) M) blocked this latter inhibition.
CONCLUSIONS:
Large doses of Arecaidine (1 g/kg subcutaneous) marginally reduced the lethal effects of bicuculline in mice but appeared to have little or no anticonvulsant activity.

Transport of the areca nut alkaloid arecaidine by the human proton-coupled amino acid transporter 1 (hPAT1).[Pubmed: 23488788 ]

J Pharm Pharmacol. 2013 Apr;65(4):582-90.

The pyridine alkaloid Arecaidine is an ingredient of areca nut preparations. It is responsible for many physiological effects observed during areca nut chewing. However, the mechanism underlying its oral bioavailability has not yet been studied. We investigated whether the H⁺-coupled amino acid transporter 1 (PAT1, SLC36A1), which is expressed in the intestinal epithelium, accepts Arecaidine, arecoline, isoguvacine and other derivatives as substrates.
METHODS AND RESULTS:
Inhibition of L-[³H]proline uptake by Arecaidine and derivatives was determined in Caco-2 cells expressing hPAT1 constitutively and in HeLa cells transiently transfected with hPAT1-cDNA. Transmembrane transport of Arecaidine and derivatives was measured electrophysiologically in Xenopus laevis oocytes. Arecaidine, guvacine and isoguvacine but not arecoline strongly inhibited the uptake of L-[³H]proline into Caco-2 cells. Kinetic analyses revealed the competitive manner of L-proline uptake inhibition by Arecaidine. In HeLa cells transfected with hPAT1-cDNA an affinity constant of 3.8 mm was obtained for Arecaidine. Electrophysiological measurements at hPAT1-expressing X. laevis oocytes demonstrated that Arecaidine, guvacine and isoguvacine are transported by hPAT1 in an electrogenic manner.
CONCLUSIONS:
We conclude that hPAT1 transports Arecaidine, guvacine and isoguvacine across the apical membrane of enterocytes and that hPAT1 might be responsible for the intestinal absorption of these drug candidates.

Protocol of Arecaidine

Animal Research

Diffusion of reduced arecoline and arecaidine through human vaginal and buccal mucosa.[Pubmed: 8667258 ]

J Oral Pathol Med. 1996 Feb;25(2):65-8.

The purpose of the present study was to determine the minimal Arecaidine concentrations showing a synergistic effect on DMBA-induced hamster cheek pouch carcinogenesis.
METHODS AND RESULTS:
One hundred and twelve male adult Syrian golden hamsters were divided into 16 groups, each containing seven animals. After eight weeks of DMBA initiation and then four weeks of Arecaidine promotion, 100% tumor incidence was found with Arecaidine concentrations of 400 micrograms/ml and 500 micrograms/ml; average tumor numbers were 1.86 +/- 0.63 and 1.86 +/- 0.93 respectively (P < 0.05). After four weeks of DMBA and a subsequent eight weeks of Arecaidine painting, all hamsters developed visible tumors with Arecaidine concentrations of 900 micrograms/ml and 1000 micrograms/ml; average tumor numbers were 1.86 +/- 0.82 and 2.14 +/- 1.09 respectively (P < 0.05). The tumor dimensions varied little and differences were not statistically significant. Without DMBA pretreatment, regardless of the high Arecaidine concentrations (1000 micrograms/ml, 2000 micrograms/ml and 3000 micrograms/ml) applied, no visible tumor growth was observed; only hyperkeratosis and inflammation could be discerned histologically.
CONCLUSIONS:
Thus, the minimal concentrations of Arecaidine displaying a synergistic effect in the DMBA-induced hamster cheek pouch of carcinogenesis were found to be 400 micrograms/ ml applied for four weeks after eight weeks of DMBA application, and 900 micrograms/ml applied for eight weeks after four weeks of DMBA painting. These findings may be useful for other studies concerning the tumorgenicity of Arecaidine.

Arecaidine Dilution Calculator

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Arecaidine Molarity Calculator

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Preparing Stock Solutions of Arecaidine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 7.0837 mL 35.4183 mL 70.8366 mL 141.6732 mL 177.0915 mL
5 mM 1.4167 mL 7.0837 mL 14.1673 mL 28.3346 mL 35.4183 mL
10 mM 0.7084 mL 3.5418 mL 7.0837 mL 14.1673 mL 17.7091 mL
50 mM 0.1417 mL 0.7084 mL 1.4167 mL 2.8335 mL 3.5418 mL
100 mM 0.0708 mL 0.3542 mL 0.7084 mL 1.4167 mL 1.7709 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Arecaidine

Development and validation of a rapid LC-MS/MS method for simultaneous quantification of arecoline and its two active metabolites in rat plasma and its application to a pharmacokinetic study.[Pubmed:29573735]

J Pharm Biomed Anal. 2018 May 30;154:397-403.

Arecoline is the primary active and toxic constituent of areca nut. Arecaidine and arecoline N-oxide are two major active metabolites of arecoline. In this work, an accurate and simple high performance liquid chromatography tandem mass spectrometry method for simultaneous quantification of arecoline, Arecaidine and arecoline N-oxide in rat plasma was developed and fully validated to study their pharmacokinetic behaviors in rats. After extracted from rat plasma by protein precipitation with methanol and then concentrated, the analytes were chromatographic separated on a Sepax Sapphire C18 analytical column. The mobile phase consisted of methanol and 2mM ammonium acetate buffer solution containing 0.2% (v/v) formic acid (8:92, v/v) under isocratic elution. The analytes were detected by multiple reaction monitoring (MRM) with an electrospray ionization source in the positive ion mode. The transitions of m/z 156.2-->53.2,m/z 142.2-->44.2 and m/z 172.2-->60.2 were selected for arecoline, Arecaidine and arecoline N-oxide, respectively. The method was linear over the concentration range of 0.5-100ng/mL for arecoline, 5-5000ng/mL for Arecaidine and arecoline N-oxide with no carry-over effect. The accuracies and intra- and inter-batch precisions were all within the acceptance limits. No matrix effect and potential interconversion between the analytes and other metabolites were observed in this method. The validated method was further employed to a preclinical pharmacokinetic study of arecoline, Arecaidine and arecoline N-oxide after oral treatment with 20mg/kg arecoline to rats.

M2 muscarinic receptor activation inhibits cell proliferation and migration of rat adipose-mesenchymal stem cells.[Pubmed:29227527]

J Cell Physiol. 2018 Jul;233(7):5348-5360.

Mesenchymal stem cells (MSCs), also known as stromal mesenchymal stem cells, are multipotent cells, which can be found in many tissues and organs as bone marrow, adipose tissue and other tissues. In particular MSCs derived from Adipose tissue (ADSCs) are the most frequently used in regenerative medicine because they are easy to source, rapidly expandable in culture and excellent differentiation potential into adipocytes, chondrocytes, and other cell types. Acetylcholine (ACh), the most important neurotransmitter in Central nervous system (CNS) and peripheral nervous system (PNS), plays important roles also in non-neural tissue, but its functions in MSCs are still not investigated. Although MSCs express muscarinic receptor subtypes, their role is completely unknown. In the present work muscarinic cholinergic effects were characterized in rat ADSCs. Analysis by RT-PCR demonstrates that ADSCs express M1-M4 muscarinic receptor subtypes, whereas M2 is one of the most expressed subtype. For this reason, our attention was focused on M2 subtype. By using the selective M2 against Arecaidine Propargyl Ester (APE) we performed cell proliferation and migration assays demonstrating that APE causes cell growth and migration inhibition without affecting cell survival. Our results indicate that ACh via M2 receptors, may contribute to the maintaining of the ADSCs quiescent status. These data are the first evidence that ACh, via muscarinic receptors, might contribute to control ADSCs physiology.

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