4730 T3D4675 Arecoline 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. 63-75-2 2230 C8H13NO2 Odourless oily liquid. < 25°C 209°C 1E+006 mg/L (at 25°C) Ingestion 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) LD50: 100 mg/kg, administered subcutaneously in mouse (Wikipedia) Not listed by IARC. 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). 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. Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms). Pupillary constriction, bronchial constriction. 2014-09-11T02:04:24Z 2026-05-14T18:07:50Z http://en.wikipedia.org/wiki/Arecoline C10129 101022 DB04365 true COC(=O)C1=CCCN(C)C1 C8H13NO2 InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3 HJJPJSXJAXAIPN-UHFFFAOYSA-N 155.1943 155.094628665 Exogenous Liquid 0.35 HMDB30353 13872064 <p>K. S. Keshave Murthy, Allan W. Rey, Dan S. Matu, &#8220;Preparation of 1,2,5,6-tetra-hydro-3-carboalkoxypridines such as arecoline and salts of 1,2,5,6-tetrahydro-3-carboalkoxypridines and arecoline hydrobromide.&#8221; U.S. Patent US6132286, issued October 17, 2000.</p> CHEM003633 DTXSID3022617 NS00002617 methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate 29.54 43.861000000000004 17.102589891012038 2 2 0 8.225681392301013 1 1 0.55 0.46 4.46e+02 g/l