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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
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. It is a competitive GABA reuptake inhibitor. Lime is said to hydrolyse arecoline to arecaidine

References

1. 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.
2. ^ 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.

• Piperidine alkaloids
• Beta-Amino acids
• GABA reuptake inhibitors