Desmethoxyyangonin
Appearance
Names | |
---|---|
Preferred IUPAC name
4-Methoxy-6-[(E)-2-phenylethen-1-yl]-2H-pyran-2-one | |
Other names
(E)-4-Methoxy-6-styryl-2H-pyran-2-one
5,6-Dehydrokavain 4-Methoxy-6-[(E)-2-phenylvinyl]-2-pyranone | |
Identifiers | |
3D model (JSmol)
|
|
ChEMBL | |
ChemSpider | |
PubChemCID
|
|
UNII | |
CompTox Dashboard(EPA)
|
|
| |
| |
Properties | |
C14H12O3 | |
Molar mass | 228.247g·mol−1 |
Appearance | white to faint yellow powder |
Density | 1.18 g/mL |
Melting point | 148 °C (298 °F; 421 K) |
Boiling point | 440 °C (824 °F; 713 K) |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
|
Desmethoxyyangoninor5,6-dehydrokavainis one of the six mainkavalactonesfound in thePiper methysticum(kava) plant.
Pharmacology[edit]
Desmethoxyyangonin is a reversibleinhibitorofmonoamine oxidase B(MAO-B).[1]Kava is able to increasedopaminelevels in thenucleus accumbens[2]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 aGABAAreceptor positive allosteric modulator.[3]
Desmethoxyyangonin has marked activity on the induction ofCYP3A23.[4]
See also[edit]
References[edit]
- ^Uebelhack, R; Franke L; Schewe HL (September 1998). "Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava)".Pharmacopsychiatry.31(5): 187–192.doi:10.1055/s-2007-979325.PMID9832350.S2CID25270815.
- ^Baum, SS; Hill R; Rommelspacher H (October 1998). "Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats".Progress in Neuro-Psychopharmacology and Biological Psychiatry.22(7): 1105–1120.doi:10.1016/S0278-5846(98)00062-1.PMID9829291.S2CID24377397.
- ^Boonen, G.; Häberlein, H. (1998)."Influence of genuine kavapyrone enantiomers on the GABA-A binding site".Planta Medica.64(6): 504–506.doi:10.1055/s-2006-957502.PMID9776662.S2CID45511040.
- ^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.PMID15282211.S2CID43840844.
{{cite journal}}
:CS1 maint: numeric names: authors list (link)