Without altering the expression of p21/Cip1, arecoline causes the generation of reactive oxygen species and cell cycle arrest in the G1/G0 phase in HaCaT cells. Higher arecoline concentrations promote epithelial cell death, however oxidative damage rather than apoptosis is the reason. The stress-responsive genes hemeoxygenase-1, ferritin light chain, glucose-6-phosphate dehydrogenase, glutamate cysteine ligase catalytic subunit, and glutathione reductase are all upregulated in expression when exposed to arecoline [1].

[1]. Regulation of oxidative-stress responsive genes by arecoline in human keratinocytes. J Periodontal Res. 2009 Oct;44(5):673-82.

[2]. The pharmacology, toxicology and potential applications of arecoline: a review. Pharm Biol. 2016 Nov;54(11):2753-2760.

[3]. DARK Classics in Chemical Neuroscience: Arecoline. ACS Chem Neurosci. 2019 May 15;10(5):2176-2185.

[4]. Arecoline induces TNF-alpha production and Zonula Occludens-1 redistribution in mouse Sertoli TM4 cells. J Biomed Sci. 2014 Sep 9;21(1):93.

Arecoline is a tetrahydropyridine compound with the structure 1,2,5,6-tetrahydropyridine, with a methyl group at position 1 and a methoxycarbonyl group at position 3. It is an alkaloid found in areca nut and acts as an agonist of muscarinic acetylcholine receptors. It is both a muscarinic receptor agonist and a metabolite. It is a tetrahydropyridine compound, as well as an acrylate, a pyridine alkaloid, and a methyl ester. Arecoline is an alkaloid extracted from areca nut (Areca catechu, the fruit of a palm tree). It is an agonist of both muscarinic and nicotinic acetylcholine receptors. It is used in various salt forms as a ganglion stimulant, a parasympathomimetic, and an anthelmintic, particularly in veterinary medicine. In the Pacific Islands, arecoline has been used as a stimulant. Arecoline has been reported to be found in areca nut (Areca catechu) and betel leaf (Piper betle), and there is available data. Arecoline is also found in nuts. Arecoline is isolated from the areca nut. Arecoline is a natural alkaloid found in the fruit of the areca nut tree (Areca catechu). It is an oily liquid, soluble in water, alcohols, and ether. Due to its properties as a muscarinic and nicotinic receptor agonist, arecoline has been shown to improve learning abilities in healthy volunteers. Since cognitive decline is a hallmark of Alzheimer's disease, arecoline has been proposed as a treatment to slow this process. Intravenous arecoline can indeed slightly improve verbal and spatial memory in Alzheimer's patients, but because of its potential carcinogenicity, it is not a first-line treatment for this degenerative disease. Arecoline has been shown to have pro-apoptotic, excitatory, and steroid-producing functions (A7876, A7878, A7879). Arecoline belongs to the alkaloid and derivative family. These natural compounds primarily contain basic nitrogen atoms. This family also includes some related compounds with neutral or even weakly acidic properties. Some structurally similar synthetic compounds are also classified as alkaloids. In addition to carbon, hydrogen, and nitrogen, alkaloids may also contain oxygen, sulfur, and less commonly, other elements such as chlorine, bromine, and phosphorus. Arecoline is an alkaloid extracted from the areca nut (Areca catechu, the fruit of a palm tree). It is an agonist of muscarinic and nicotinic acetylcholine receptors. It is used in various salt forms as a ganglion stimulant, parasympathomimetic, and anthelmintic, particularly in veterinary medicine. It was once used as a stimulant on Pacific islands.

155.095

63-75-2

Arecoline hydrobromide;300-08-3;Arecoline hydrochloride;61-94-9

2230

Light yellow to brown liquid

1.059g/cm3

209ºC at 760mmHg

< 25 °C

81.1ºC

1.483

0.359

0

3

2

11

187

0

HJJPJSXJAXAIPN-UHFFFAOYSA-N

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

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

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

H2O : ~250 mg/mL (~1610.93 mM)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

---

Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

View More

Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

---

Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

View More

Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

---

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

---

 (Please use freshly prepared in vivo formulations for optimal results.)