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Revision as of 08:14, 20 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').← Previous edit		Latest revision as of 06:57, 5 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers30,619 edits Add: s2cid.
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	{{chembox		{{chembox
			|Verifiedfields = changed
⚫	| verifiedrevid = 399892399
			|Watchedfields = changed
⚫	|ImageFile=Desmethoxyyangonin.svg
		⚫	|verifiedrevid = 456483554
⚫	|IUPACName=4-methoxy-6--2''H''-pyran-2-one
		⚫	|ImageFile1=Desmethoxyyangonin.svg
⚫	|OtherNames=5,6-Dehydrokawain<br/>4-methoxy-6--2-pyranone
			|ImageFile2=Desmethoxyyangonin02.png
		⚫	|PIN = 4-Methoxy-6--2''H''-pyran-2-one
		⚫	|OtherNames = (''E'')-4-Methoxy-6-styryl-2''H''-pyran-2-one<br />5,6-Dehydrokavain<br />4-Methoxy-6--2-pyranone
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4438012		|ChemSpiderID = 4438012
	| InChI = 1/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+		|InChI = 1/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+
	| InChIKey = DKKJNZYHGRUXBS-BQYQJAHWBF		|InChIKey = DKKJNZYHGRUXBS-BQYQJAHWBF
	| SMILES1 = O=C/1O\C(=CC(\OC)=C\1)\C=C\c2ccccc2		|SMILES1 = O=C/1O\C(=CC(\OC)=C\1)\C=C\c2ccccc2
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+		|StdInChI = 1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = DKKJNZYHGRUXBS-BQYQJAHWSA-N		|StdInChIKey = DKKJNZYHGRUXBS-BQYQJAHWSA-N
			|CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = <!-- blanked - oldvalue: 1952-41-6 -->
			|CASNo=15345-89-8
⚫	| ChEMBL = 254218
			|UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem=5273621
			|UNII = F2MBQ8QRUN
⚫	| SMILES=COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫	}}
		⚫	|ChEMBL = 254218
		⚫	|PubChem=5273621
		⚫	|SMILES=COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2
		⚫	}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| C=14 |H=12 |O=3		|C=14 | H=12 | O=3
	| Appearance=		|Appearance= white to faint yellow powder
	| Density=		|Density= 1.18 g/mL
			|MeltingPtC= 148
	| MeltingPt=
			|BoilingPtC= 440
	| BoilingPt=
		⚫	}}
	| Solubility=
⚫	}}
	|Section3={{Chembox Hazards
	| MainHazards=
	| FlashPt=
	| Autoignition=
	}}
	}}		}}
	'''Desmethoxyyangonin''' or '''5,6-dehydrokawain''' is one of the six major ]s found in the '']'' (kava) plant.		'''Desmethoxyyangonin''' or '''5,6-dehydrokavain''' is one of the six main ]s found in the '']'' (kava) plant.
	==Pharmacology==		==Pharmacology==
			Desmethoxyyangonin is a reversible ] of ] (MAO-B).<ref>{{cite journal|last=Uebelhack|first=R|author2=Franke L |author3=Schewe HL |title=Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava)|journal=Pharmacopsychiatry|date=September 1998|volume=31|issue=5|pages=187–192|doi=10.1055/s-2007-979325|pmid=9832350|s2cid=25270815}}</ref> Kava is able to increase ] levels in the ]<ref>{{cite journal|last=Baum|first=SS|author2=Hill R |author3=Rommelspacher H |title=Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats|journal=Progress in Neuro-Psychopharmacology and Biological Psychiatry|date=October 1998|volume=22|issue=7|pages=1105–1120|doi=10.1016/S0278-5846(98)00062-1|pmid=9829291|s2cid=24377397}}</ref> and desmethoxyyangonin likely contributes to this effect. This, along with several other catecholamines, may be responsible for the purported attention-promoting effects of kava.
			Unlike the other major kavalactones, desmethoxyyangonin does not appear to act as a ].<ref>{{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 }}</ref>
	Desmethoxyyangonin is a reversible ] of ] (MAO-B). It is able to increase ] levels in the ]. This may be the reason for the ] from Kava consumption.
	Desmethoxyyangonin 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|pmid=15282211|doi=10.1124/dmd.104.000786}}</ref>		Desmethoxyyangonin 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=November 2004|first=Yuzhong|last=Ma|author2=Karuna Sachdeva |author3=Jirong Liu1 |author4=Michael Ford |author5=Dongfang Yang |author6=Ikhlas Khan |author7=Clinton Chichester |author8=Bingfang Yan |volume=32|issue=11|pages=1317–1324|pmid=15282211|doi=10.1124/dmd.104.000786|s2cid=43840844}}</ref>
		⚫	==See also==
		⚫	*]
	==References==		==References==
	{{reflist}}		{{Reflist|2}}
⚫	==See also==
⚫	*]
	{{Kava}}		{{Kava}}
			{{Dopaminergics}}
	]		]
	]		]
	]		]
	]		]
			]
	{{nervous-system-drug-stub}}