Arecoline

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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	C₈H₁₃N O₂
Mol. mass	155.194 g/mol
SMILES	search in 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 a natural organic compound which is an alkaloid found in betel nuts from the betel palm (Areca catechu).^[1] It is an oily liquid that is soluble in water, alcohols, and ether.

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 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.).

Arecoline has also been used medicinally as an antihelmintic (a drug against parasitic worms).

[edit] 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. 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.