Dihydromethysticin: Difference between revisions

Browse history interactively ← Previous editContent deleted Content addedVisual WikitextInline

Revision as of 05:59, 19 April 2011 editCheMoBot (talk \| contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit		Latest revision as of 01:02, 28 December 2022 edit undoAllforrous (talk \| contribs)Extended confirmed users27,554 edits →References: Commonscatinline template.
(41 intermediate revisions by 25 users not shown)
Line 1:		Line 1:
	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~370104879~~
			\| 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}}

	]		]
			]
			]
			]

Latest revision as of 01:02, 28 December 2022

Dihydromethysticin
Names
Chemical structure of dihydromethysticin
3D Chemical structure of dihydromethysticin
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

Chemical compound

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

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.
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)
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.
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.
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

[REDACTED] Media related to Dihydromethysticin at Wikimedia Commons

Kava

History

Chemical composition

Kavalactones	Desmethoxyyangonin Dihydrokavain Dihydromethysticin Kavain Methysticin Yangonin
Flavokavains	Flavokavain A Flavokavain B Flavokavain C
Other	Pipermethystine

v t e GABA_A receptor positive modulators
Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol
Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital
Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Bromazolam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Dimdazenil Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam
Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Hydroxyphenamate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate
Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin
Imidazoles	Etomidate Metomidate Propoxate
Kava constituents	10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Posovolone Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone
Nonbenzodiazepines	Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684
Phenols	Fospropofol Propofol Thymol
Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione
Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether
Others/unsorted	3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Nicotinic acid Nicotinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol) Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators