Dihydromethysticin facts for kids

Quick facts for kids Dihydromethysticin
IUPAC name	(2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
Identifiers
CAS number	19902-91-1
PubChem	88308
MeSH	C107882
SMILES	COC1=CC(=O)OC(C1)CCC2=CC3=C(C=C2)OCO3
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
Properties
Molecular formula	C15H16O5
Molar mass	276.28 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Dihydromethysticin is one of the six major kavalactones found in the kava plant.

Pharmacology

Dihydromethysticin has marked activity on the induction of CYP3A23, as does the related chemical desmethoxyyangonin.

Both dihydromethysticin and methysticin induce the hepatic enzyme CYP1A1, which increases the amount of the very highly carcinogenic benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide in the body (via the metabolism of benzo[a]pyrene) and may be responsible for some of the toxic effects associated with kava consumption.

Metabolism of benzo[a]pyrene yielding the carcinogenic benzo[a]pyren-7,8-dihydrodiol-9,10-epoxide.

In vitro, dihydromethysticin possesses analgesic, anticonvulsant, and anxiolytic effects. It has been found to act as a GABA_A receptor positive allosteric modulator and as an reversible inhibitor of monoamine oxidase B.