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Dihydromethysticin

Names
IUPAC name (2S)-2--4-methoxy-2,3-dihydropyran-6-one
Identifiers
CAS Number	19902-91-1
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1510786
ChemSpider	200147
MeSH	C107882
PubChem CID	88308
UNII	FZ66MQ73GS
CompTox Dashboard (EPA)	DTXSID601314143
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,2,4,7,9H2,1H3Key: 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 , 100 kPa). N verify (what is  ?) Infobox references

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

Pharmacology

Dihydromethysticin has marked activity on the induction of CYP3A23, as does the related chemical desmethoxyyangonin.

Both dihydromethysticin and methysticin induce the hepatic enzyme CYP1A1, which increases the amount of the very highly carcinogenic benzopyrene-7,8-dihydrodiol-9,10-epoxide in the body (via the metabolism of benzopyrene) and may be responsible for some of the toxic effects associated with kava consumption.

In vitro, dihydromethysticin possesses analgesic, anticonvulsant, and anxiolytic effects. It has been found to act as a GABA_A receptor positive allosteric modulator and as an reversible inhibitor of monoamine oxidase B.

References

1. Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF). Fiji School of Medicine. Archived from the original (PDF) on 2009-03-20. 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. S2CID 43840844.{{cite journal}}: CS1 maint: numeric names: authors list (link)
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. S2CID 34014477.
4. Sarris, Jerome; Laporte, Emma; Schweitzer, Isaac (2011). "Kava: A Comprehensive Review of Efficacy, Safety, and Psychopharmacology". Australian & New Zealand Journal of Psychiatry. 45 (1): 27–35. doi:10.3109/00048674.2010.522554. PMID 21073405. S2CID 42935399.
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. S2CID 34322458.

External links

• Media related to Dihydromethysticin at Wikimedia Commons

• Kavalactones
• Cytochrome P450 inhibitors
• GABAA receptor positive allosteric modulators
• Monoamine oxidase inhibitors