Dihydromethysticin

Dihydromethysticin
Names
	IUPAC name (2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
Identifiers
CAS Number	19902-91-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1510786 ;
ChemSpider	200147 ;
MeSH	C107882
PubChem CID	88308;
UNII	FZ66MQ73GS ;
CompTox Dashboard (EPA)	DTXSID601314143 ;
	InChI InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3 Key: RSIWXFIBHXYNFM-UHFFFAOYSA-N;
	SMILES COC1=CC(=O)OC(C1)CCC2=CC3=C(C=C2)OCO3;
Properties
Chemical formula	C15H16O5
Molar mass	276.28 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dihydromethysticin is one of the six major kavalactones found in the kava plant. It is known for its anxiolytic, analgesic, and anticonvulsant properties. It induces the liver enzymes CYP1A1 and CYP3A through mechanisms involving the aryl hydrocarbon receptor and potentially pregnane X receptor-independent transcriptional activation. Dihydromethysticin acts synergistically with other kavalactones, modulates NMDA receptors and voltage-dependent calcium channels, and functions as a GABAA receptor positive allosteric modulator and monoamine oxidase B inhibitor. Dihydromethysticin shows high systemic exposure and rapid absorption in humans, suggesting it is a major contributor to kava’s effects.