Guvacine

Last updated

Guvacine
1,2,5,6-tetrahydropyridine-3-carboxylic acid.svg
Clinical data
Drug class GABA reuptake inhibitor
ATC code
  • None
Identifiers
  • 1,2,5,6-tetrahydropyridine-3-carboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C6H9NO2
Molar mass 127.143 g·mol−1
3D model (JSmol)
  • C1CNCC(=C1)C(=O)O
  • 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

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. The compound is a potent and selective GABA reuptake inhibitor via GABA transporter 1 (GAT-1) inhibition. [2] [3] [4] It shows poor blood–brain barrier penetration. [5] Lime hydrolyzes guvacoline to guvacine. [6]

See also

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. ↑ Krogsgaard-Larsen P (June 1980). "Inhibitors of the GABA uptake systems". Molecular and Cellular Biochemistry. 31 (2): 105–121. doi:10.1007/BF00240816. PMID   6251361.
  3. ↑ Krogsgaard-Larsen P, Frølund B, Frydenvang K (August 2000). "GABA uptake inhibitors. Design, molecular pharmacology and therapeutic aspects". Current Pharmaceutical Design. 6 (12): 1193–1209. doi:10.2174/1381612003399608. PMID   10903390.
  4. ↑ Soudijn W, van Wijngaarden I (October 2000). "The GABA transporter and its inhibitors". Current Medicinal Chemistry. 7 (10): 1063–1079. doi:10.2174/0929867003374363. PMID   10911018.
  5. ↑ Armer RE (February 2000). "Inhibitors of mammalian central nervous system selective amino acid transporters". Current Medicinal Chemistry. 7 (2): 199–209. doi:10.2174/0929867003375380. PMID   10637362.
  6. ↑ 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.
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