Dihydromethysticin

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Dihydromethysticin
Chemical structure of dihydromethysticin
Identifiers
CAS number 19902-91-1 YesY
PubChem 88308
Jmol-3D images Image 1
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 (77 °F), 100 kPa)
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Infobox references

Dihydromethysticin is one of the six major kavalactones found in the kava plant.[1]

Pharmacology[edit]

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 BP-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.

Dihydromethysticin possesses analgesic, anticonvulsant, and anxiolytic effects.[3]

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

References[edit]

  1. ^ Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver". Fiji School of Medicine. Retrieved 2009-09-04. 
  2. ^ Ma, Yuzhong; Karuna Sachdeva; Jirong Liu1; Michael Ford; Dongfang Yang; Ikhlas Khan; Clinton Chichester; Bingfang Yan (November 2004). "Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23.". Drug Metabolism and Disposition 32 (11): 1317–1324. doi:10.1124/dmd.104.000786. PMID 15282211. 
  3. ^ Walden J, von Wegerer J, Winter U, Berger M, Grunze H (May 1997). "Effects of kawain and dihydromethysticin on field potential changes in the hippocampus.". Progress in Neuro-psychopharmacology and Biological Psychiatry 21 (4): 697–706. PMID 9194150. 

See also[edit]