Methysticin

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 424844893

| ImageFile1 = Methysticin.svg

| ImageSize1 = 200px

| ImageFile2 = Methysticin02.png

| ImageSize2 = 200px

| PIN = (6R)-6-[(E)-2-(2H-1,3-Benzodioxol-5-yl)ethen-1-yl]-4-methoxy-5,6-dihydro-2H-pyran-2-one

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|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 495-85-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = M832AIJ6HX

| PubChem = 5281567

| SMILES = COC1=CC(=O)O[C@H](C1)/C=C/C2=CC3=C(C=C2)OCO3

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4444889

| InChI = 1/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1

| InChIKey = GTEXBOVBADJOQH-FWEMWIAWBD

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2+/t11-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GTEXBOVBADJOQH-FWEMWIAWSA-N

| RTECS =

| MeSHName =

| ChEBI =

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C09952

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|Section2={{Chembox Properties

| C=15 | H=14 | O=5

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|Section3={{Chembox Hazards

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Methysticin 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|url-status=dead|archive-url=https://web.archive.org/web/20090320001735/http://www.spc.int/cis/documents/Kava%20article%20DrMalani.pdf|archive-date=2009-03-20}} Research suggests that methysticin and the related compound dihydromethysticin have CYP1A1 inducing effects which may be responsible for their toxicity.{{cite journal|title=Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.|vauthors=Li Y, Mei H, Wu Q, Zhang S, Fang JL, Shi L, Guo L |journal=Toxicological Sciences|pmid=21908763|doi=10.1093/toxsci/kfr235|volume=124|issue=2|date=Dec 2011|pages=388–99|pmc=5736320}} Additionally, methysticin has been shown to potentiate GABA_A receptor activity, contributing to the overall anxiolytic profile of the kava plant.{{cite journal | url=https://pubmed.ncbi.nlm.nih.gov/9776662/ | pmid=9776662 | year=1998 | last1=Boonen | first1=G. | last2=Häberlein | first2=H. | title=Influence of genuine kavapyrone enantiomers on the GABA-A binding site | journal=Planta Medica | volume=64 | issue=6 | pages=504–506 | doi=10.1055/s-2006-957502 | s2cid=45511040 }}