Arecoline

drugbox
IUPAC_name = methyl1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

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CAS_number = 63-75-2
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PubChem = 2230
DrugBank = EXPT03296
C=8 | H=13 | N=1 | O=2
molecular_weight = 155.194 g/mol
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smiles = O=C(OC)C1=CCCN(C)C1
density = 1.0495
melting_point =
boiling_point = 209

Arecoline is an alkaloid-type natural product found in the areca nut, the fruit of the areca palm ("Areca catechu").cite journal | author=Ghelardini C, Galeotti N, Lelli C, Bartolini A. | title=Arecoline M1 receptor activation is a requirement for arecoline analgesia. | journal=Farmaco. | year=2001 | pages=383–5 | volume=56 | issue=5–7 | pmid=11482763 | doi=10.1016/S0014-827X(01)01091-6] 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,cite journal | author=Yang YR, Chang KC, Chen CL, Chiu TH. | title=Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor. | journal=Chin J Physiol. | year=2000 | pages=23–8 | volume=43 | issue=1 | pmid=10857465] cite journal | author=Xie DP, Chen LB, Liu CY, Zhang CL, Liu KJ, Wang PS. | title=Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits. | journal=Chin J Physiol. | year=2004 | pages=89–94 | volume=47 | issue=2 | pmid=15481791] 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, cite journal | author=Saikia JR, Schneeweiss FH, Sharan RN. | title=Arecoline-induced changes of poly-ADP-ribosylation of cellular proteins and its influence on chromatin organization. | journal=Cancer Letters. | year=1999 | pages=59–65 | volume=139 | issue=1 | pmid=10408909 | doi=10.1016/S0304-3835(99)00008-7] it is not the first drug of choice for this degenerative disease. cite journal | journal=British Journal of Psychiatry | author=Christie JE, Shering A, Ferguson J | title=Physostigmine and arecoline: effects of intravenous infusions in Alzheimer’s presenile dementia | year=1981 | pages=46–50 | volume=138 | pmid=7023592]

Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms).cite journal |author=Yusuf H, Yong SL |title=Oral submucous fibrosis in a 12-year-old Bangladeshi boy: a case report and review of literature |journal=International journal of paediatric dentistry / the British Paedodontic Society [and] the International Association of Dentistry for Children |volume=12 |issue=4 |pages=271–6 |year=2002 |pmid=12121538 |doi=]

References