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Desmethoxyyangonin

Names
Preferred IUPAC name 4-Methoxy-6--2H-pyran-2-one
Other names (E)-4-Methoxy-6-styryl-2H-pyran-2-one 5,6-Dehydrokavain 4-Methoxy-6--2-pyranone
Identifiers
CAS Number	15345-89-8
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL254218
ChemSpider	4438012
PubChem CID	5273621
UNII	F2MBQ8QRUN
CompTox Dashboard (EPA)	DTXSID4033390
InChI 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+Key: DKKJNZYHGRUXBS-BQYQJAHWSA-N 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
SMILES COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2 O=C/1O\C(=CC(\OC)=C\1)\C=C\c2ccccc2
Properties
Chemical formula	C14H12O3
Molar mass	228.247 g·mol
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 , 100 kPa). N verify (what is  ?) Infobox references

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

Pharmacology

Desmethoxyyangonin is a reversible inhibitor of monoamine oxidase B (MAO-B). Kava is able to increase dopamine levels in the nucleus accumbens 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 GABA_A receptor positive allosteric modulator.

Desmethoxyyangonin has marked activity on the induction of CYP3A23.

See also

• Kavain

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. S2CID 25270815.
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. S2CID 45511040.
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.{{cite journal}}: CS1 maint: numeric names: authors list (link)

• Monoamine oxidase inhibitors
• Kavalactones
• Alkene derivatives
• Ethers
• Nootropics