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
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL1510786
ChemSpider	200147
MeSH	C107882
PubChem	88308
UNII	G9X3XK922J
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).
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Infobox references

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

Pharmacology

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.

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.^[3] It has been found to act as a GABA_A receptor positive allosteric modulator and as an reversible inhibitor of monoamine oxidase B.^[4][5]

References

1. Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF). 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. doi:10.1016/s0278-5846(97)00042-0. PMID 9194150.
4. Sarris J, LaPorte E, Schweitzer I (2011). "Kava: a comprehensive review of efficacy, safety, and psychopharmacology". Aust N Z J Psychiatry. 45 (1): 27–35. doi:10.3109/00048674.2010.522554. PMID 21073405.
5. Singh YN, Singh NN (2002). "Therapeutic potential of kava in the treatment of anxiety disorders". CNS Drugs. 16 (11): 731–43. doi:10.2165/00023210-200216110-00002. PMID 12383029.