Arecaidine

Arecaidine
Clinical data
Other names	Methylguvacine; Arecaine; N-Methylguvacine
Identifiers
	IUPAC name 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid;
CAS Number	499-04-7;
PubChem CID	10355;
IUPHAR/BPS	9487;
ChemSpider	9928;
UNII	0S8YEV0D4O;
KEGG	C10128;
ChEBI	CHEBI:2813;
ChEMBL	ChEMBL432561;
CompTox Dashboard (EPA)	DTXSID60198139 ;
Chemical and physical data
Formula	C7H11NO2
Molar mass	141.170 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC=C(C1)C(=O)O;
	InChI InChI=1S/C7H11NO2/c1-8-4-2-3-6(5-8)7(9)10/h3H,2,4-5H2,1H3,(H,9,10); Key:DNJFTXKSFAMXQF-UHFFFAOYSA-N;

Arecaidine is a bio-active alkaloid in areca nuts.^[1] It is a competitive GABA reuptake inhibitor.^[2] Lime is said to hydrolyse arecoline to arecaidine^[2]

References

^ Voigt V, Laug L, Zebisch K, Thondorf I, Markwardt F, Brandsch M (April 2013). "Transport of the areca nut alkaloid arecaidine by the human proton-coupled amino acid transporter 1 (hPAT1)". The Journal of Pharmacy and Pharmacology. 65 (4): 582–590. doi:10.1111/jphp.12006. PMID 23488788. S2CID 27577546.
^ ^a ^b Johnston GA, Krogsgaard-Larsen P, Stephanson A (December 1975). "Betel nut constituents as inhibitors of gamma-aminobutyric acid uptake". Nature. 258 (5536): 627–628. Bibcode:1975Natur.258..627J. doi:10.1038/258627a0. PMID 1207742. S2CID 4147760.