Desmethoxyyangonin

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

Desmethoxyyangonin
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
UNII
  • InChI=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+ checkY
    Key: DKKJNZYHGRUXBS-BQYQJAHWSA-N checkY
  • 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+
    Key: DKKJNZYHGRUXBS-BQYQJAHWBF
  • COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2
  • O=C/1O\C(=CC(\OC)=C\1)\C=C\c2ccccc2
Properties
C14H12O3
Molar mass 228.247 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pharmacology

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 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 GABAA receptor positive allosteric modulator.[3]

Desmethoxyyangonin has marked activity on the induction of CYP3A23.[4]

See also

References
  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. S2CID 24377397.
  3. 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. PMID 9776662.
  4. 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.
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