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6-Methylapigenin

GABAA PAM, flavonoid From Wikipedia, the free encyclopedia

6-Methylapigenin is a naturally occurring flavonoid and a derivative of apigenin. It has activity at GABAA receptors as a positive modulator.

Quick facts Names, Identifiers ...
6-Methylapigenin
Names
IUPAC name
5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-methylchromen-4-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • Key: ZLGRXDWWYMFIGI-UHFFFAOYSA-N
  • InChI=1S/C16H12O5/c1-8-11(18)6-14-15(16(8)20)12(19)7-13(21-14)9-2-4-10(17)5-3-9/h2-7,17-18,20H,1H3
  • CC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC=C(C=C3)O)O
Properties
C16H12O5
Molar mass 284.267 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Natural occurrence

6-Methylapigenin can be found in multiple plants, such as Valeriana officinalis, Valeriana jatamansi, and Picea neoveitchii.[1]

Biological activity

6-Methylapigenin binds to the GABAA receptor on the benzodiazepine binding site. This compound possesses anxiolytic effects. In a mouse model, it is also able to potentiate sleep induced by hesperidin, another flavonoid.[2][3] However, since it does not have the chemical structure of benzodiazepines, it can therefore be classed as a nonbenzodiazepine.

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