Arecoline

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



width = 149



CAS_number = 63-75-2
ATC_prefix =
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PubChem = 2230
DrugBank = EXPT03296
C=8 | H=13 | N=1 | O=2
molecular_weight = 155.194 g/mol
bioavailability =
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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


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Look at other dictionaries:

  • Arecoline — A*re co*line, n. Also lin lin . [From NL. Areca, a genus of palms bearing betel nut.] An oily liquid substance, {C8H13O2N}, the chief alkaloid of the betel nut, to which the latter owes its anthelmintic action. Syn: arecholine; arecaline;… …   The Collaborative International Dictionary of English

  • arecoline — noun Etymology: International Scientific Vocabulary areca + 1 ol + 2 ine Date: 1894 a toxic parasympathomimetic alkaloid C8H13NO2 that is used as a veterinary anthelmintic and occurs naturally in betel nuts …   New Collegiate Dictionary

  • arecoline — /euh ree keuh leen , lin, euh rek euh , ar i keuh /, n. a toxic alkaloid obtained from the seeds of the areca, used chiefly in veterinary medicine as an agent for killing and expelling intestinal worms. [AREC(A) + OL1 + INE2] * * * …   Universalium

  • arecoline — A colorless oily alkaloid from the betel nut. * * * arec·o·line ə rek ə .lēn n a toxic parasympathomimetic alkaloid C8H13NO2 that is used as a veterinary anthelmintic and occurs naturally in betel nuts * * * arec·o·line (ə rekґo lēn) a… …   Medical dictionary

  • arecoline — are·co·line …   English syllables

  • arecoline — əˈrēkəˌlēn, lə̇n noun ( s) Etymology: International Scientific Vocabulary arec (from New Latin Areca) + ol + ine : a colorless oily toxic alkaloid C8H13NO2 that is a derivative of nicotinic acid and constitutes the active principle of betel nuts… …   Useful english dictionary

  • C8H13O2N — Arecoline A*re co*line, n. Also lin lin . [From NL. Areca, a genus of palms bearing betel nut.] An oily liquid substance, {C8H13O2N}, the chief alkaloid of the betel nut, to which the latter owes its anthelmintic action. Syn: arecholine;… …   The Collaborative International Dictionary of English

  • -lin — Arecoline A*re co*line, n. Also lin lin . [From NL. Areca, a genus of palms bearing betel nut.] An oily liquid substance, {C8H13O2N}, the chief alkaloid of the betel nut, to which the latter owes its anthelmintic action. Syn: arecholine;… …   The Collaborative International Dictionary of English

  • arec — [ arɛk ] n. m. • 1610 arecque; 1525 arcea; mot port., par l it. 1 ♦ Vx Fruit de l aréquier. 2 ♦ (1653) Mod. Aréquier. Noix d arec : fruit de cet arbre, dont l amande contient du cachou et entre dans la composition du bétel. ● arec nom masculin… …   Encyclopédie Universelle

  • aréquier — [ arekje ] n. m. • 1687; port. arequero; cf. arec ♦ Grand palmier d Asie équatoriale dont le fruit est la noix d arec et dont le bourgeon terminal (cœur de palmier ou chou palmiste) est comestible. ● aréquier nom masculin (portugais areca, du… …   Encyclopédie Universelle


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