Dihydromethysticin
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424812230
| Name = Dihydromethysticin
| ImageFile = Dihydromethysticin.svg
| ImageName = Chemical structure of dihydromethysticin
| ImageAlt = Chemical structure of dihydromethysticin
| ImageFile2 = File:Dihydromethysticim 3D BS.png
| ImageName2 = 3D Chemical structure of dihydromethysticin
| ImageAlt2 = 3D Chemical structure of dihydromethysticin
| IUPACName =
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 19902-91-1
| CASNoOther =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1510786
| PubChem = 88308
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FZ66MQ73GS
| SMILES = COC1=CC(=O)OC(C1)CCC2=CC3=C(C=C2)OCO3
| 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
| InChIKey = RSIWXFIBHXYNFM-UHFFFAOYSA-N
| MeSHName = C107882
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 200147
}}
|Section2={{Chembox Properties
| Formula = C15H16O5
| MolarMass = 276.28 g/mol
| Appearance =
| Density =
| MeltingPt =
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Dihydromethysticin is one of the six major kavalactones found in the kava plant.{{cite journal|title=Evaluation of the effects of Kava on the Liver|journal=Fiji School of Medicine|date=2002-12-03|first=Joji|last=Malani|url=http://www.spc.int/cis/documents/Kava%20article%20DrMalani.pdf|access-date=2009-09-04|archive-url=https://web.archive.org/web/20090320001735/http://www.spc.int/cis/documents/Kava%20article%20DrMalani.pdf|archive-date=2009-03-20|url-status=dead}}
Pharmacology
Dihydromethysticin has marked activity on the induction of CYP3A23, as does the related chemical desmethoxyyangonin.{{cite journal|last=Ma|first=Yuzhong|date=November 2004|title=Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23.|journal=Drug Metabolism and Disposition|volume=32|issue=11|pages=1317–1324|doi=10.1124/dmd.104.000786|pmid=15282211|author2=Karuna Sachdeva|author3=Jirong Liu1|author4=Michael Ford|author5=Dongfang Yang|author6=Ikhlas Khan|author7=Clinton Chichester|author8=Bingfang Yan|s2cid=43840844}}
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|date=June 2017}}
File:Benzo(a)pyrene metabolism.svg benzo[a]pyren-7,8-dihydrodiol-9,10-epoxide.]]{{clear left}}
In vitro, dihydromethysticin possesses analgesic, anticonvulsant, and anxiolytic effects.{{cite journal|title=Effects of kawain and dihydromethysticin on field potential changes in the hippocampus.|vauthors=Walden J, von Wegerer J, Winter U, Berger M, Grunze H |journal=Progress in Neuro-Psychopharmacology and Biological Psychiatry|pmid=9194150|volume=21|issue=4|date=May 1997|pages=697–706|doi=10.1016/s0278-5846(97)00042-0|s2cid=34014477 }} It has been found to act as a GABAA receptor positive allosteric modulator and as an reversible inhibitor of monoamine oxidase B.{{cite journal |doi=10.3109/00048674.2010.522554 |pmid=21073405 |title=Kava: A Comprehensive Review of Efficacy, Safety, and Psychopharmacology |journal=Australian & New Zealand Journal of Psychiatry |volume=45 |issue=1 |pages=27–35 |year=2011 |last1=Sarris |first1=Jerome |last2=Laporte |first2=Emma |last3=Schweitzer |first3=Isaac |s2cid=42935399 }}{{cite journal | vauthors = Singh YN, Singh NN | title = Therapeutic potential of kava in the treatment of anxiety disorders | journal = CNS Drugs | volume = 16 | issue = 11 | pages = 731–43 | year = 2002 | pmid = 12383029 | doi = 10.2165/00023210-200216110-00002| s2cid = 34322458 }}
References
{{Reflist|2}}
External links
- {{Commonscatinline|Dihydromethysticin}}
{{Kava}}
{{GABAAR PAMs}}
{{Dopaminergics}}
Category:Cytochrome P450 inhibitors