Methysticin

Methysticin
Names
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
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/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 N
    Key: GTEXBOVBADJOQH-FWEMWIAWSA-N N
  • 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
    Key: GTEXBOVBADJOQH-FWEMWIAWBD
  • COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3
Properties
C15H14O5
Molar mass 274.272 g·mol−1
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

Methysticin is one of the six major kavalactones found in the kava plant. It enhances the activity of the GABAA receptor, acting as a positive modulator without affecting the benzodiazepine binding site. This effect is attributed to structural features such as its angular lactone ring and is similar in strength to other kavalactones like kavain and dihydromethysticin. Methysticin also induces the liver enzyme CYP1A1, which plays a role in the toxification of benzo[a]pyrene into a highly carcinogenic metabolite, although such induction has not been observed in vivo in humans or animals. Additionally, methysticin is a mechanism-based inactivator of CYP2C9, irreversibly inhibiting the enzyme through NADPH-dependent reactive intermediates, suggesting potential interactions with medications metabolized by CYP2C9.

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