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Arecoline

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Arecoline chemical structure
Arecoline

methyl1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
IUPAC name
CAS number
63-75-2
ATC code

[[ATC_code_|]][1]

PubChem
2230
DrugBank
EXPT03296
Chemical formula {{{chemical_formula}}}
Molecular weight 155.194 g/mol
Bioavailability
Metabolism
Elimination half-life
Excretion
Pregnancy category
Legal status
Routes of administration

Arecoline is an alkaloid-type natural product found in betel nuts from the betel palm (Areca catechu).[1] It is an oily liquid that is soluble in water, alcohols, and ether.

MechanismEdit

In many Asian cultures, the betel nut is chewed to obtain a stimulating effect. Arecoline is the primary active ingredient responsible for the central nervous system affects 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,[1][2][3] which is believed to be the primary cause of its parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.).

UsesEdit

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]


See alsoEdit

ReferencesEdit

  1. 1.0 1.1 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. PMID 11482763.
  2. 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.
  3. 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.
  4. 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. PMID 10408909.
  5. 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.
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