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20-September-2008 09:55:55 - Arecoline Arecoline Systematic IUPAC name methyl1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate Identifiers CAS number 63-75-2 ATC code ? PubChem 2230 DrugBank EXPT03296 Chemical data Formula C8H13NO2 Mol. mass 155.194 g/mol SMILES eMolecules PubChem Physical data Density 1.0495 g/cm³ Boiling point 209 °C 408 °F Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Routes ? Arecoline is an alkaloid-type natural product found in the areca nut, the fruit of the areca palm Areca catechu.1 It is an oily liquid that is soluble in water, alcohols, and ether. Mechanism In many Asian cultures, the areca nut is chewed along with betel leaf to obtain a stimulating effect. Arecoline is the primary active ingredient responsible for the central nervous system effects which are roughly comparable to those of nicotine, which has a similar chemical structure. Arecoline is known to be an agonist of muscarinic acetylcholine M1, M2 and M3 receptors,123 which is believed to be the primary cause of its parasympathetic effects such as pupillary constriction, bronchial constriction, etc.. Uses 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, 4 it is not the first drug of choice for this degenerative disease. 5 Arecoline has also been used medicinally as an antihelmintic a drug against parasitic worms.6 Tablets This pharmacology-related article is a stub. References ^ a b Ghelardini C, Galeotti N, Lelli C, Bartolini A. 2001. Arecoline M1 receptor activation is a requirement for arecoline analgesia.. Farmaco. 56 5-7: 383-5. doi:10.1016/S0014-827X0101091-6. PMID 11482763. ^ Yang YR, Chang KC, Chen CL, Chiu TH. 2000. Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor.. Chin J Physiol. 43 1: 23-8. PMID 10857465. ^ Xie DP, Chen LB, Liu CY, Zhang CL, Liu KJ, Wang PS. 2004. Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits.. Chin J Physiol. 47 2: 89-94. PMID 15481791. ^ Saikia JR, Schneeweiss FH, Sharan RN. 1999. Arecoline-induced changes of poly-ADP-ribosylation of cellular proteins and its influence on chromatin organization.. Cancer Letters. 139 1: 59-65. doi:10.1016/S0304-38359900008-7. PMID 10408909. ^ Christie JE, Shering A, Ferguson J 1981. Physostigmine and arecoline: effects of intravenous infusions in Alzheimer's presenile dementia. British Journal of Psychiatry 138: 46-50. PMID 7023592. ^ Yusuf H, Yong SL 2002. Oral submucous fibrosis in a 12-year-old Bangladeshi boy: a case report and review of literature. International journal of paediatric dentistry / the British Paedodontic Society and the International Association of Dentistry for Children 12 4: 271-6. PMID 12121538. v d e Parasympathomimetics / cholinergic agonists / acetylcholinesterase inhibitors N06DA, N07AA Direct at receptor muscarinic: Muscarine - Oxotremorine - M1 Xanomeline - M3 Bethanechol, Pilocarpine, Arecoline, Cevimeline, Aceclidine nicotinic: Nicotine - Lobeline - Varenicline - Epibatidine M N: Acetylcholine/Choline alfoscerate - Methacholine - Carbachol Indirect/AIs in synapse Reversible carbamates: Ambenonium - Stigmine Neostigmine, Physostigmine, Pyridostigmine, Rivastigmine, Distigmine Edrophonium anti-dementia Galantamine, Donepezil, Tacrine Irreversible/ organophosphate ophthalmological Echothiophate, Isoflurophate antiparasitic Malathion, Metrifonate chemical warfare see Nerve agent Retrieved from http://en..org/wiki/Arecoline Categories: Pharmacology stubs | Muscarinic agonists | Nitrogen heterocycles | Carboxylate esters | Nicotinic agonists Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Italiano Polski Svenska This page was last modified on 31 July 2008, at 19:52
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