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Purity: ≥98%
Arecoline HBr (NSC56321, NSC-56321), the hydrobromide salt of Arecoline which is a naturally occurring alkaloid found in the betel nut of the Areca palm, is a potent agonist of muscarinic acetylcholine receptor with the potential to be used in treating dementia. It activates the M1, M2, M3, M4, and M5 subtype of muscarinic acetylcholine receptors with EC50 values of 7, 95, 11, 410, and 69 nM, respectively.
ln Vitro |
Without altering the expression of p21/Cip1, arecoline hydrobromide causes HaCaT cells to undergo cell cycle arrest in the G1/G0 phase and produce reactive oxygen species. At greater quantities, arecoline hydrobromide induces epithelial cell death that results from oxidative damage rather than apoptosis. 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 hydrobromide [1].
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Toxicity/Toxicokinetics |
Toxicity Summary
Arecoline is the primary active ingredient responsible for the central nervous system effects of the areca nut. Arecoline has been compared to nicotine; however, nicotine acts primarily on the nicotinic acetylcholine receptor. Arecoline is known to be a partial agonist of muscarinic acetylcholine M1, M2, M3 receptors and M4, which is believed to be the primary cause of its parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.). (Wikipedia) Arecoline is cytotoxic to human gingival fibroblasts at a concentration higher than 50 μg/ml by depleting intracellular thiols and inhibiting mitochondrial activity (P<0.05). In addition, the cells displayed a marked arrest at G2/M phase in a dose-dependent manner. (A15351) Toxicity Data LD50: 100 mg/kg, administered subcutaneously in mouse (Wikipedia) |
References |
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Additional Infomation |
Arecoline is a tetrahydropyridine that is 1,2,5,6-tetrahydropyridine with a methyl group at position 1, and a methoxycarbonyl group at position 3. An alkaloid found in the areca nut, it acts as an agonist of muscarinic acetylcholine. It has a role as a muscarinic agonist and a metabolite. It is a tetrahydropyridine, an enoate ester, a pyridine alkaloid and a methyl ester.
An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands. Arecoline has been reported in Areca catechu and Piper betle with data available. Arecoline is found in nuts. Arecoline is isolated from betel nuts Arecoline is an alkaloid natural product found in the areca nut, the fruit of the areca palm (Areca catechu). It is an oily liquid that is soluble in water, alcohols, and ether. Owing to its muscarinic and nicotinic agonist properties, arecoline has shown improvement in the learning ability of healthy volunteers. Since one of the hallmarks of Alzheimer's disease is a cognitive decline, arecoline was suggested as a treatment to slow down this process and arecoline administered via i.v. route did indeed show modest verbal and spatial memory improvement in Alzheimer's patients, though due to arecoline's possible carcinogenic properties, it is not the first drug of choice for this degenerative disease. Arecoline has been shown to exhibit apoptotic, excitant and steroidogenic functions (A7876, A7878, A7879). Arecoline belongs to the family of Alkaloids and Derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. An alkaloid obtained from the betel nut (Areca catechu), fruit of a palm tree. It is an agonist at both muscarinic and nicotinic acetylcholine receptors. It is used in the form of various salts as a ganglionic stimulant, a parasympathomimetic, and a vermifuge, especially in veterinary practice. It has been used as a euphoriant in the Pacific Islands. |
Molecular Formula |
C8H13NO2.HBR
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Molecular Weight |
236.11
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Exact Mass |
235.02
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CAS # |
300-08-3
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Related CAS # |
Arecoline;63-75-2;Arecoline hydrochloride;61-94-9
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PubChem CID |
2230
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Appearance |
White to light yellow solid powder
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Boiling Point |
209ºC at 760mmHg
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Melting Point |
171-175 °C
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Flash Point |
81.1ºC
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LogP |
1.317
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Hydrogen Bond Donor Count |
0
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Hydrogen Bond Acceptor Count |
3
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Rotatable Bond Count |
2
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Heavy Atom Count |
11
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Complexity |
187
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Defined Atom Stereocenter Count |
0
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InChi Key |
AXOJRQLKMVSHHZ-UHFFFAOYSA-N
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InChi Code |
InChI=1S/C8H13NO2.BrH/c1-9-5-3-4-7(6-9)8(10)11-2;/h4H,3,5-6H2,1-2H3;1H
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Chemical Name |
methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrobromide
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Synonyms |
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
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Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (8.81 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (8.81 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (423.53 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 4.2353 mL | 21.1766 mL | 42.3531 mL | |
5 mM | 0.8471 mL | 4.2353 mL | 8.4706 mL | |
10 mM | 0.4235 mL | 2.1177 mL | 4.2353 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.