Guvacine

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 checkY
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
  • 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
Chemical compound

Guvacine is an hydrogenated pyridine 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 is said to hydrolyse guvacoline to guvacine.[2]

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.
  • v
  • t
  • e
GABATooltip γ-Aminobutyric acid metabolism and transport modulators
Transporter
GATTooltip GABA transporter
VIAATTooltip Vesicular inhibitory amino acid transporter
Enzyme
GADTooltip Glutamate decarboxylase
GABA-TTooltip γ-Aminobutyrate aminotransferase
Other
Antivitamin B6
See also
Receptor/signaling modulators
GABA receptor modulators
GABAA receptor positive modulators
Glutamate metabolism/transport modulators