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guvacine
Sign in to saveAlso known as 1,2,5,6-tetrahydronicotinic acid, 1,2,5,6-tetrahydro-3-pyridinecarboxylic acid
Guvacine is a tetrahydropyridine alkaloid found in areca nuts. 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. It shows poor blood–brain barrier penetration. Lime hydrolyzes guvacoline to guvacine.
Chemical data
- Formula
- C6H9NO2
- Molecular weight
- 127.14 g/mol
- IUPAC name
- 1,2,3,6-tetrahydropyridine-5-carboxylic acid
- SMILES
- C1CNCC(=C1)C(=O)O
- InChIKey
- QTDZOWFRBNTPQR-UHFFFAOYSA-N
- XLogP
- -2.5
- Polar surface area
- 49.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- alkaloid
- Mass
- 127.063329
Show 4 more facts
- chemical formula
- C₆H₉NO₂
- canonical SMILES
- C1CNCC(=C1)C(=O)O
- found in taxon
- Areca catechu
- Commons category
- Guvacine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Guvacine is a tetrahydropyridine alkaloid found in areca nuts. 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. It shows poor blood–brain barrier penetration. Lime hydrolyzes guvacoline to guvacine.
== See also == Nipecotic acid THPO Isoguvacine Tiagabine
Excerpted from Wikipedia’s “guvacine” article, available under the CC BY-SA 4.0 licence.