Desmethoxyyangonin

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Desmethoxyyangonin
Desmethoxyyangonin.svg
Desmethoxyyangonin02.png
Names
IUPAC name
4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one
Other names
5,6-Dehydrokawain
4-methoxy-6-[(E)-2-phenylvinyl]-2-pyranone
Identifiers
15345-89-8 N
ChEMBL ChEMBL254218 YesY
ChemSpider 4438012 YesY
Jmol-3D images Image
Image
PubChem 5273621
Properties
C14H12O3
Molar mass 228.24 g·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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Desmethoxyyangonin or 5,6-dehydrokawain is one of the six major kavalactones found in the Piper methysticum (kava) plant.

Pharmacology[edit]

Desmethoxyyangonin is a reversible inhibitor of monoamine oxidase B (MAO-B).[1] Kava is able to increase dopamine levels in the nucleus accumbens[2] and desmethoxyyangonin likely contributes to this effect. This, along with the potential increases of serotonin and other catecholamine concentrations, may be responsible for the purported attention-promoting effects of kava.

Desmethoxyyangonin has marked activity on the induction of CYP3A23.[3]

References[edit]

  1. ^ 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. PMID 9832350. 
  2. ^ 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. PMID 9829291. 
  3. ^ 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.