Desmethoxyyangonin

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
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−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). 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).^[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 GABA_A receptor positive allosteric modulator.^[3]

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

References

^ 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.
^ 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.
^ 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.
^ 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)

[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.

[Ma_2004-4] 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)

[1]

[2]

[3]

[4]

Desmethoxyyangonin

Pharmacology

See also

References