Arecoline

Arecoline
Clinical data


ATC code	none
Legal status
Legal status	Uncontrolled
Identifiers
IUPAC name Methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
CAS Number	63-75-2^Y
PubChem (CID)	2230
IUPHAR/BPS	296
DrugBank	DB04365^Y
ChemSpider	13872064^Y
UNII	4ALN5933BH^Y
KEGG	C10129^Y
ChEBI	CHEBI:2814^N
ChEMBL	CHEMBL7303^Y
ECHA InfoCard	100.000.514
Chemical and physical data
Formula	C₈H₁₃NO₂
Molar mass	155.194 g/mol
3D model (Jmol)	Interactive image
Density	1.0495 g/cm³
Boiling point	209 °C (408 °F)
SMILES O=C(OC)C=1CN(C)CCC=1
InChI InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3^Y Key:HJJPJSXJAXAIPN-UHFFFAOYSA-N^Y
^NY (what is this?)

Arecoline (/əˈrɛkəliːn/) is a nicotinic acid-based alkaloid found in the areca nut, the fruit of the areca palm (Areca catechu). It is an odourless oily liquid.

Arecoline is a base, and its conjugate acid has a pK_a ~ 6.8. Arecoline is volatile in steam, miscible with most organic solvents and water, but extractable from water by ether in presence of dissolved salts. Being basic, arecoline forms salts with acids. The salts are crystalline, but usually deliquescent: the hydrochloride, arecoline•HCl, forms needles, m.p. 158 °C; the hydrobromide, arecoline•HBr, forms slender prisms, mp. 177-179 °C from hot alcohol; the aurichloride, arecoline•HAuCl₄, is an oil, but the platinichloride, arecoline₂•H₂PtCl₆, mp. 176 °C, crystallizes from water in orange-red rhombohedrons. The methiodide forms glancing prisms, mp. 173-174 °C.

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 of the areca nut. Arecoline has been compared to nicotine; however, nicotine acts primarily on the nicotinic acetylcholine receptor. Arecoline is known to be a partial agonist of muscarinic acetylcholine M₁, M₂, M₃ receptors and M₄, which is believed to be the primary cause of its parasympathetic effects (such as pupillary constriction, bronchial constriction, etc.).

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