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 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1510786 N
ChemSpider	200147 N
MeSH	C107882
PubChem CID	88308
UNII	FZ66MQ73GS Y
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). N verify (what is YN ?) Infobox references

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.

External links

• Media related to Dihydromethysticin at Wikimedia Commons