5,7-Dihydroxy-6-methoxy-2-(4-phenoxyphenyl)chromen-4-one

5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one (DMPC) is a derivative of oroxylin A. It has memory improving effects and can reduce ADHD-like behavior.

5,7-Dihydroxy-6-methoxy-2-(4-phenoxyphenyl)chromen-4-one[1]
Names
IUPAC name
5,7-dihydroxy-6-methoxy-2-(4-phenoxyphenyl)chromen-4-one
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C22H16O6/c1-26-22-17(24)12-19-20(21(22)25)16(23)11-18(28-19)13-7-9-15(10-8-13)27-14-5-3-2-4-6-14/h2-12,24-25H,1H3
    Key: FUBRAMOFTBBVFU-UHFFFAOYSA-N
  • COC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC=C(C=C3)OC4=CC=CC=C4)O
Properties
C22H16O6
Molar mass 376.364 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Mechanism of action

As a derivative of oroxylin A, it has similar activity; in rats, DMPC has been shown to block the reuptake of dopamine similarly to methylphenidate, however it does not act at the norepinephrine transporter. This has resulted in attenuated ADHD-like behavior, but unlike methylphenidate and other ADHD medication, it did not display addictive properties. Which could make it useful as a non-addictive ADHD drugs, as most currently used ADHD stimulants have addictive properties.[3]

DMPC also possesses memory improving properties, it is able to attenuate memory impairment induced by scopolamine and MK-801. It also had memory-enhancing effects if administered alone.[4]

DMPC is able to block the chloride influx induced by muscimol at GABAA receptors, suggesting that it is a GABAA antagonist or negative modulator.[4]

References
  1. "5,7-Dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4h-chromene-4-one".
  2. "5,7-Dihydroxy-6-methoxy-4-phenoxyflavone CAS#: 1342207-75-3".
  3. dela Peña, Ike C.; Young Yoon, Seo; Kim, Yeni; Park, Haeil; Man Kim, Kyeong; Hoon Ryu, Jong; Young Shin, Chan; Hoon Cheong, Jae (2013-09-05). "5,7-Dihydroxy-6-methoxy-4'-phenoxyflavone, a derivative of oroxylin A improves attention-deficit/hyperactivity disorder (ADHD)-like behaviors in spontaneously hypertensive rats". European Journal of Pharmacology. 715 (1–3): 337–344. doi:10.1016/j.ejphar.2013.05.002. ISSN 1879-0712. PMID 23707903.
  4. Liu, Xiaotong; Hong, Sung In; Park, Se Jin; Dela Peña, June Bryan; Che, Haiyan; Yoon, Seo Young; Kim, Dong Hyun; Kim, Jong Min; Cai, Mudan; Risbrough, Victoria; Geyer, Mark A.; Shin, Chan Young; Cheong, Jae Hoon; Park, Haeil; Lew, Jae Hwan (July 2013). "The ameliorating effects of 5,7-dihydroxy-6-methoxy-2(4-phenoxyphenyl)-4H-chromene-4-one, an oroxylin A derivative, against memory impairment and sensorimotor gating deficit in mice". Archives of Pharmacal Research. 36 (7): 854–863. doi:10.1007/s12272-013-0106-6. ISSN 1976-3786. PMID 23543630. S2CID 255556700.


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