Methysticin facts for kids

Quick facts for kids Methysticin
Preferred IUPAC name (6R)-6-[(E)-2-(2H-1,3-Benzodioxol-5-yl)ethen-1-yl]-4-methoxy-5,6-dihydro-2H-pyran-2-one
Identifiers
CAS number	495-85-2
PubChem	5281567
KEGG	C09952
SMILES	COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3
InChI InChI=1/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1
Properties
Molecular formula	C15H14O5
Molar mass	274.24 g mol-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Methysticin is one of the six major kavalactones found in the kava plant. Research suggests that methysticin and the related compound dihydromethysticin have CYP1A1 inducing effects which may be responsible for their toxicity.

Toxicity

Methysticin induces the function of the hepatic enzyme CYP1A1. This enzyme is involved in the toxification of benzo[a]pyrene into (+)-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide, a highly carcinogenic substance. Another related compound is dihydromethysticin, which also induces the function of CYP1A1. No report so far has described enhancement of CYP1A1 expression in animals or humans in vivo from any constituent of kava.