Arecoline

Arecoline
Clinical data
Other names	Arecaline; Arecholine; Arecolin; Arecoline base; Arekolin; Methylarecaidin
ATC code	none;
Legal status
Legal status	AU: S4 (Prescription only) ; UK: Could be illegal to sell for human consumption under the Psychoactive Substances Act or if is synthetized for recreational use[citation needed]; US: Unscheduled;
Identifiers
	IUPAC name Methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate;
CAS Number	63-75-2 ;
PubChem CID	2230;
IUPHAR/BPS	296;
DrugBank	DB04365 ;
ChemSpider	13872064 ;
UNII	4ALN5933BH;
KEGG	C10129 ;
ChEBI	CHEBI:2814 ;
ChEMBL	ChEMBL7303 ;
CompTox Dashboard (EPA)	DTXSID3022617 ;
ECHA InfoCard	100.000.514
Chemical and physical data
Formula	C8H13NO2
Molar mass	155.197 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.0495 g/cm3
Melting point	27 °C (81 °F)
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 ; Key:HJJPJSXJAXAIPN-UHFFFAOYSA-N ;
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Arecoline (/əˈrɛkəliːn/) is a nicotinic acid-based mild parasympathomimetic stimulant alkaloid found in the areca nut, the fruit of the areca palm (Areca catechu).^[2] It is an odourless oily liquid. It can bring a sense of enhanced alertness and energy along with mild feelings of euphoria and relaxation.

^ "Poisons Standard October 2020". Federal Register of Legislation. The Australian Government. 30 September 2020.
^ Ghelardini C, Galeotti N, Lelli C, Bartolini A (2001). "M1 receptor activation is a requirement for arecoline analgesia". Farmaco. 56 (5–7): 383–385. doi:10.1016/S0014-827X(01)01091-6. hdl:2158/327019. PMID 11482763.

[1] "Poisons Standard October 2020". Federal Register of Legislation. The Australian Government. 30 September 2020.

[ArecolineM1-Ghelardini-2] Ghelardini C, Galeotti N, Lelli C, Bartolini A (2001). "M1 receptor activation is a requirement for arecoline analgesia". Farmaco. 56 (5–7): 383–385. doi:10.1016/S0014-827X(01)01091-6. hdl:2158/327019. PMID 11482763.

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