kavain

Also known as kawain

Kavain is the principal kavalactone found in the roots of the kava plant (Piper methysticum), where it contributes significantly to the plant's psychoactive and anxiolytic effects.

Chemical data

Formula: C14H14O3
Molecular weight: 230.26 g/mol
IUPAC name: (2R)-4-methoxy-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

152 papers

Kavain Alleviates Choroidal Neovascularization Via Decreasing the Activity of the HIF-1α/VEGF-A/VEGFR2 Signaling Pathway and Inhibiting Inflammation.Advanced pharmaceutical bulletin · 2024
Kavain for health promotion and disease mitigation: Pharmacological promise and therapeutic perspectives.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2026
Enzymes and Pathways of Kavain Bioactivation and Biotransformation.Chemical research in toxicology · 2019
Kavain Interference with Amphetamine Immunoassay.Journal of analytical toxicology · 2020
Kavain suppresses human Aβ-induced paralysis in C. elegans.microPublication biology · 2020

via PubMed

Wikidata facts

Mass: 230.094294

Show 4 more facts

chemical formula: C₁₄H₁₄O₃
Commons category: Kavain
isomeric SMILES: COC1=CC(=O)O[C@H](C1)/C=C/C2=CC=CC=C2
canonical SMILES: COC1=CC(=O)OC(C1)C=CC2=CC=CC=C2

Sources (2)

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~3 min read

Article

3 sections

Contents

Pharmacology
See also
References

Kavain is the principal kavalactone found in the roots of the kava plant (Piper methysticum), where it contributes significantly to the plant's psychoactive and anxiolytic effects.

Kavain exhibits anticonvulsant properties by modulating voltage-dependent sodium and calcium channels, and it may influence mood and anxiety through reversible inhibition of monoamine oxidase A and monoamine oxidase B, potentially affecting serotonin, dopamine, and norepinephrine signaling. Although it does not bind to the benzodiazepine site of GABAA receptors, kavain potentiates GABA activity at extrasynaptic α4β2δ GABAA receptors and overlaps with the modulatory pathways of certain general anesthetics. It also shows weak sodium antagonism, strong L-type calcium channel blockade, and enhances early potassium currents, suggesting mood-stabilizing effects akin to lamotrigine.