Guvacine

Guvacine is a tetrahydropyridine alkaloid found in areca nuts.^[1] It is the N-demethylated derivative of arecaidine and the product of ester hydrolysis of guvacoline, both of which are also found in areca nuts as well. It is also an inhibitor of gamma-aminobutyric acid uptake. Lime hydrolyzes guvacoline to guvacine.^[2]

Guvacine

Names
Preferred IUPAC name 1,2,5,6-Tetrahydropyridine-3-carboxylic acid
Identifiers
CAS Number	498-96-4
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL76768
ChemSpider	3412
IUPHAR/BPS	4691
KEGG	C10149
PubChem CID	3532
UNII	41538P325K Y
CompTox Dashboard (EPA)	DTXSID50871702
InChI InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9) Key: QTDZOWFRBNTPQR-UHFFFAOYSA-N InChI=1/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9) Key: QTDZOWFRBNTPQR-UHFFFAOYAX
SMILES C1CNCC(=C1)C(=O)O
Properties
Chemical formula	C6H9NO2
Molar mass	127.143 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

References

1. Voigt, V; Laug, L; Zebisch, K; Thondorf, I; Markwardt, F; Brandsch, M (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): 582–90. doi:10.1111/jphp.12006. PMID 23488788. S2CID 27577546.
2. Johnston, G. A. R.; Krogsgaard-Larsen, P.; Stephanson, A. (1975). "Betel nut constituents as inhibitors of γ-aminobutyric acid uptake". Nature. 258 (5536): 627–628. Bibcode:1975Natur.258..627J. doi:10.1038/258627a0. ISSN 0028-0836. PMID 1207742. S2CID 4147760.