From Wikipedia, the free encyclopedia
Arecoline is an alkaloid natural product found in the areca nut, the fruit of the
areca palm (Areca catechu).[1]
It is an odourless oily liquid volatile in steam, miscible with
most organic solvents and water, but extractable from the latter by
ether in presence of dissolved salts. The
salts are crystalline, but usually deliquescent; the hydrobromide,
B•HBr, forms slender prisms, mp. 177-9 °C from hot alcohol; the aurichloride,
B•HAuCl4, is an oil, but the platinichloride,
B2•H2PtCl6, mp. 176 °C,
crystallises from water in orange-red rhombs. The methiodide forms glancing
prisms, mp. 173-4 °C.
Mechanism
In many Asian cultures, the areca nut is chewed along with betel
leaf to obtain a stimulating effect.[2]
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 a
partial agonist of muscarinic acetylcholine
M1, M2 and M3 receptors,[1][3][4]
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, [5]
it is not the first drug of choice for this degenerative disease.
[6]
Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic
worms).[7]
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/S0014-827X(01)01091-6. PMID 11482763.
- ^
Gupta Prakash Chandra, Ray Cecily S
(July 2004). "Epidemiology of betel quid
usage". Ann. Acad. Med. Singap. 33 (4
Suppl): 31–6. PMID 15389304. http://www.annals.edu.sg/pdf200409/V33N4p31S.pdf.
- ^ 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/S0304-3835(99)00008-7. 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. doi:10.1192/bjp.138.1.46. 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.
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Receptor
Ligands |
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Agonists:
77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B
• AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 •
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WAY-132,983 • Xanomeline • YM-796
Antagonists: 3-Quinuclidinyl Benzilate •
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Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 •
Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 •
CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 •
Cyclobenzaprine • Cyclopentolate •
Darifenacin •
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Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Anatruxonium • Atracurium • Bupropion (Amfebutamone) •
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Reuptake
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Enzyme
Inhibitors |
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1-(-Benzoylethyl)pyridinium •
2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole •
4-(1-Naphthylvinyl)pyridine • Acetylseco Hemicholinium-3 •
Acryloylcholine • AF64A • B115 • BETA • CM-54,903 •
N,N-Dimethylaminoethylacrylate •
N,N-Dimethylaminoethylchloroacetate
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Many of the
acetylcholinesterase inhibitors listed above act as
butyrylcholinesterase inhibitors.
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Others |
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