Dihydromethysticin is one of the six major kavalactones found in the kava plant.[1]
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IUPAC name
(2S)-2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-methoxy-2,3-dihydropyran-6-one
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3D model (JSmol)
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MeSH | C107882 |
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Properties | |
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).
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Infobox references
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Dihydromethysticin has marked activity on the induction of CYP3A23, as does the related chemical desmethoxyyangonin.[2]
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.[citation needed]
In vitro, dihydromethysticin possesses analgesic, anticonvulsant, and anxiolytic effects.[3] It has been found to act as a GABAA receptor positive allosteric modulator and as an reversible inhibitor of monoamine oxidase B.[4][5]
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