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. 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]

Drug classGABA reuptake inhibitor

ATC code

• None

CAS Number

• 498-96-4

PubChem CID

• 3532

Quick facts Clinical data, Drug class ...

Guvacine

Clinical data
Drug class	GABA reuptake inhibitor
ATC code	None
Identifiers
IUPAC name 1,2,5,6-tetrahydropyridine-3-carboxylic acid
CAS Number	498-96-4
PubChem CID	3532
IUPHAR/BPS	4691
ChemSpider	3412
UNII	41538P325K
KEGG	C10149
ChEMBL	ChEMBL76768
CompTox Dashboard (EPA)	DTXSID50871702
Chemical and physical data
Formula	C6H9NO2
Molar mass	127.143 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CNCC(=C1)C(=O)O
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

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