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Yangonin information


Yangonin
Names
Preferred IUPAC name
4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethen-1-yl]-2H-pyran-2-one
Identifiers
CAS Number
  • 500-62-9 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1098658 ☒N
ChemSpider
  • 4444896 ☒N
ECHA InfoCard 100.211.821 Edit this at Wikidata
PubChem CID
  • 5281575
UNII
  • R970U49V3C ☒N
CompTox Dashboard (EPA)
  • DTXSID4034102 Edit this at Wikidata
InChI
  • InChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+ ☒N
    Key: XLHIYUYCSMZCCC-VMPITWQZSA-N ☒N
  • InChI=1/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+
    Key: XLHIYUYCSMZCCC-VMPITWQZBG
SMILES
  • COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=O)O2)OC
Properties
Chemical formula
C15H14O4
Molar mass 258.273 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Yangonin is one of the six major kavalactones found in the kava plant.[1] It has been shown to possess binding affinity for the cannabinoid receptor CB1 (Ki = 0.72 μM), and selectivity vs. the CB2 receptor (Ki >10 μM) where it behaves as an agonist. The CB1 receptor affinity of yangonin suggests that the endocannabinoid system might contribute to the complex human psychopharmacology of the traditional kava drink and the anxiolytic preparations obtained from the kava plant.[2]

Like other kavalactones, yangonin has been found to potentiate GABAA receptors.[3] This may contribute to the anxiolytic properties of yangonin and kava as a whole.

Further in vitro studies have also demonstrated yangonin to be an inhibitor of monoamine oxidase,[citation needed] with a moderate preference for isozyme B, which could open the door to a wide range of interactions.

  1. ^ Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF). Fiji School of Medicine. Retrieved 2009-09-04.
  2. ^ Ligresti, A.; Villano, R.; Allarà, M.; Ujváry, I. N.; Di Marzo, V. (2012). "Kavalactones and the endocannabinoid system: The plant-derived yangonin is a novel CB1 receptor ligand". Pharmacological Research. 66 (2): 163–169. doi:10.1016/j.phrs.2012.04.003. PMID 22525682.
  3. ^ "Yangonin".

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Yangonin

Last Update:

Yangonin is one of the six major kavalactones found in the kava plant. It has been shown to possess binding affinity for the cannabinoid receptor CB1 (Ki...

Word Count : 295

Kavalactone

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glucose induced cell damage. Several kavalactones (e.g., methysticin and yangonin) affect a group of enzymes involved in metabolism, called the CYP450 system...

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Kava

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of harvest. The kavalactones present are kavain, demethoxyyangonin, and yangonin, which are higher in the roots than in the stems and leaves, with dihydrokavain...

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Methaqualone

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 2382

Pentobarbital

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 1924

Nicotinamide

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 2425

Cannabinoid

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the plant structure, but are most concentrated in the roots and flowers. Yangonin found in the kava plant has significant affinity to the CB1 receptor. Tea...

Word Count : 7813

Paracetamol

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Oleamide Pravadoline Serinolamide A THC (dronabinol) UR-144 WIN 55,212-2 Yangonin Inverse agonists AM-251 INV-202 Rimonabant Surinabant Taranabant TM-38837...

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Alprazolam

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 8228

Chloroform

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 5618

Isopropyl alcohol

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

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Toluene

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

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Barbiturate

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

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Lorazepam

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 8518

Fluoxetine

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 11667

Clonazepam

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 7418

Cannabinoid receptor

Last Update:

2012). "Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB₁ receptor ligand". Pharmacological Research. 66 (2): 163–9...

Word Count : 3086

Chloral hydrate

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 4003

Carbamazepine

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 3052

Synthetic cannabinoids

Last Update:

Gallocatechol Hexahydrocannabinol (HHC) Perrottetinene Serinolamide A Yangonin Active metabolites 3'-OH-THC 7-OH-CBD 8,11-DiOH-THC 11-COOH-THC 11-OH-CBN...

Word Count : 12043

Phenobarbital

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 4935

Propane

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 5343

Midazolam

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 6727

Diethyl ether

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 2743

Menthol

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 2865

Dichloromethane

Last Update:

8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 2877

Topiramate

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8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride...

Word Count : 3780

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