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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424812230
| Name = Dihydromethysticin | Name = Dihydromethysticin
| ImageFile = Dihydromethysticin.PNG | ImageFile = Dihydromethysticin.svg
| ImageSize = 200px
| ImageName = Chemical structure of dihydromethysticin | ImageName = Chemical structure of dihydromethysticin
| ImageAlt = 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 = <nowiki>(2S)-2--4-methoxy-2,3-dihydropyran-6-one</nowiki> | IUPACName = <nowiki>(2S)-2--4-methoxy-2,3-dihydropyran-6-one</nowiki>
| OtherNames = <!-- <br> --> | OtherNames = <!-- <br> -->
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 19902-91-1 | CASNo = 19902-91-1
| CASNo_Ref = | CASNoOther =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| CASOther =
| ChEMBL = 1510786
| PubChem = 88308 | PubChem = 88308
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FZ66MQ73GS
| SMILES = COC1=CC(=O)OC(C1)CCC2=CC3=C(C=C2)OCO3 | 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
| InChI =
| InChIKey = RSIWXFIBHXYNFM-UHFFFAOYSA-N
| MeSHName = | MeSHName = C107882
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 200147
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>15</sub>H<sub>16</sub>O<sub>5</sub> | Formula = ]
| MolarMass = 276.28 g/mol | MolarMass = 276.28 g/mol
| ExactMass = 276.099774 u
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = <!-- °C --> | MeltingPt =
| BoilingPt = <!-- °C --> | BoilingPt =
| Solubility = | Solubility =
}} }}
}} }}

'''Dihydromethysticin''' is one of the six major ]s found in the ] plant.<ref name='Malani'> {{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|coauthors=|volume=|issue=|pages=|id= |url=http://www.spc.int/cis/documents/Kava%20article%20DrMalani.pdf|format=|accessdate=2009-09-04 }}</ref> '''Dihydromethysticin''' is one of the six major ]s found in the ] plant.<ref name='Malani'>{{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}}</ref>


==Pharmacology== ==Pharmacology==
Dihydromethysticin has marked activity on the induction of ].<ref name='Ma 2004'> {{cite journal|title=Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23.|journal=Drug Metabolism and Disposition|date=2004 November|first=Yuzhong|last=Ma|coauthors=Karuna Sachdeva, Jirong Liu1, Michael Ford, Dongfang Yang, Ikhlas Khan, Clinton Chichester, Bingfang Yan|volume=32|issue=11|pages=1317–1324|doi=10.1124/dmd.104.000786|url=|format=|accessdate=2009-09-04|pmid=15282211 }}</ref> Dihydromethysticin has marked activity on the induction of ], as does the related chemical ].<ref name="Ma 2004">{{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}}<!--|accessdate=2009-09-04--></ref>

Both dihydromethysticin and ] induce the hepatic enzyme ], which increases the amount of the very highly ] pyrene-7,8-dihydrodiol-9,10-epoxide]] in the body (via the metabolism of pyrene]]) and may be responsible for some of the toxic effects associated with kava consumption.{{Citation needed|date=June 2017}}

pyrene yielding the ] benzopyren-7,8-dihydrodiol-9,10-epoxide.]]{{clear left}}

'']'', dihydromethysticin possesses ], ], and ] effects.<ref>{{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 }}</ref> It has been found to act as a ] ] and as an reversible ] of ].<ref name="pmid21073405">{{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 }}</ref><ref name="pmid12383029">{{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 }}</ref>


==References== ==References==
{{reflist}} {{Reflist|2}}


==See also== ==External links==
*{{Commonscatinline|Dihydromethysticin}}
*]
*]


{{Kava}} {{Kava}}
{{GABAAR PAMs}}

{{pharma-stub}} {{Dopaminergics}}


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