Dihydrokavain

Dihydrokavain
Names
	IUPAC name 4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
	Other names Dihydrokawain; Marindinin
Identifiers
CAS Number	587-63-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	88817 ;
PubChem CID	98356;
UNII	NW8ZGW9XRZ ;
CompTox Dashboard (EPA)	DTXSID101018162 DTXSID8033433, DTXSID101018162 ;
	InChI InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3 Key: VOOYTQRREPYRIW-UHFFFAOYSA-N ; InChI=1/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3 Key: VOOYTQRREPYRIW-UHFFFAOYAX;
	SMILES COC1=CC(=O)OC(C1)CCC2=CC=CC=C2;
Properties
Chemical formula	C14H16O3
Molar mass	232.27 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dihydrokavain is one of the six major kavalactones found in the kava plant.^[1] It appears to contribute significantly to the anxiolytic effects of kava, based on a study in chicks.^[2]

Dihydrokavain bears some structural similarity to the strobilurins and has some fungicidal activity.^[3]

An analogue of the molecule was also shown to improve glycemic control by modulating AMPK target genes expression in fruit flies.^[4]

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.
^ Feltenstein, MW; LC Lambdin; M Ganzera; H Ranjith; W Dharmaratne; NP Nanayakkara; IA Khan; KJ Sufka (March 2003). "Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure". Phytotherapy Research. 17 (3): 210–216. doi:10.1002/ptr.1107. PMID 12672148. S2CID 10548965.
^ Zakharychev, Vladimir V; Kovalenko, Leonid V (1998-06-30). "Natural compounds of the strobilurin series and their synthetic analogues as cell respiration inhibitors". Russian Chemical Reviews. 67 (6): 535–544. Bibcode:1998RuCRv..67..535Z. doi:10.1070/rc1998v067n06abeh000426. ISSN 0036-021X. S2CID 95676421.
^ Hadiza Muhammad Maiturare; Mudassir Aliyu Magaji; Muhammad Kabiru Dallatu; Kabir Magaji Hamid; Mustapha Umar Imam; Ibrahim Malami (2022). "5,6-dehydrokawain improves glycaemic control by modulating AMPK target genes in Drosophila with a high-sucrose diet-induced hyperglycaemia". Phytomedicine Plus. 2 (2): 100261–. doi:10.1016/j.phyplu.2022.100261. ISSN 2667-0313. S2CID 247649601.

This article about an anxiolytic is a stub. You can help Wikipedia by expanding it.

[Malani-1] 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.

[2] Feltenstein, MW; LC Lambdin; M Ganzera; H Ranjith; W Dharmaratne; NP Nanayakkara; IA Khan; KJ Sufka (March 2003). "Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure". Phytotherapy Research. 17 (3): 210–216. doi:10.1002/ptr.1107. PMID 12672148. S2CID 10548965.

[Zakharychev-Kovalenko-1998-3] Zakharychev, Vladimir V; Kovalenko, Leonid V (1998-06-30). "Natural compounds of the strobilurin series and their synthetic analogues as cell respiration inhibitors". Russian Chemical Reviews. 67 (6): 535–544. Bibcode:1998RuCRv..67..535Z. doi:10.1070/rc1998v067n06abeh000426. ISSN 0036-021X. S2CID 95676421.

[4] Hadiza Muhammad Maiturare; Mudassir Aliyu Magaji; Muhammad Kabiru Dallatu; Kabir Magaji Hamid; Mustapha Umar Imam; Ibrahim Malami (2022). "5,6-dehydrokawain improves glycaemic control by modulating AMPK target genes in Drosophila with a high-sucrose diet-induced hyperglycaemia". Phytomedicine Plus. 2 (2): 100261–. doi:10.1016/j.phyplu.2022.100261. ISSN 2667-0313. S2CID 247649601.

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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 Niacin Niacinamide 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

Names


IUPAC name 4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
Other names Dihydrokawain Marindinin
Identifiers
CAS Number	587-63-3^Y
3D model (JSmol)	Interactive image
ChemSpider	88817^N
PubChem CID	98356
UNII	NW8ZGW9XRZ^Y
CompTox Dashboard (EPA)	DTXSID101018162 DTXSID8033433, DTXSID101018162
InChI InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3^N Key: VOOYTQRREPYRIW-UHFFFAOYSA-N^N InChI=1/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3 Key: VOOYTQRREPYRIW-UHFFFAOYAX
SMILES COC1=CC(=O)OC(C1)CCC2=CC=CC=C2
Properties
Chemical formula	C₁₄H₁₆O₃
Molar mass	232.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references