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Eutropoflavin

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(Redirected from4'-Dimethylamino-7,8-dihydroxyflavone)

Chemical compound

Pharmaceutical compound

Eutropoflavin
Clinical data

ATC code	None
Identifiers
IUPAC name 2-[4-(dimethylamino)phenyl]-7,8-dihydroxy-4H-chromen-4-one
CAS Number	1205548-04-4
PubChemCID	44610701
ChemSpider	26630138
UNII	B2M862MR4W
ChEMBL	ChEMBL1800922
CompTox Dashboard(EPA)	DTXSID901045822
Chemical and physical data
Formula	C₁₇H₁₅NO₄
Molar mass	297.310 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN(C)c1ccc(cc1)c2cc(=O)c3ccc(c(c3o2)O)O
InChI InChI=InChI=1S/C17H15NO4/c1-18(2)11-5-3-10(4-6-11)15-9-14(20)12-7-8-13(19)16(21)17(12)22-15/h3-9,19,21H,1-2H3 Key:YPAYCZOHGRSGJS-UHFFFAOYSA-N

Eutropoflavin (4'-dimethylamino-7,8-dihydroxyflavone) is asynthetic flavone-typeselective agonist ofTrkB, the mainreceptor ofbrain-derived neurotrophic factor (BDNF), which was derived fromstructural modification oftropoflavin (7,8-DHF).^[1]^[2]^[3]^[4] Relative to tropoflavin, eutropoflavin possesses higher agonistic activity at TrkB, is significantly more potent than tropoflavin bothin vitro andin vivo, and has a longer duration of action (peaking at 4 hours and "partially decaying" at 8~16 hours in rodents).^[1]^[3] The compound has been found to produceneuroprotective andneurogenic effects in the brain and spinal cord as well asantidepressant-like effects in animals.^[1]^[3]^[4]^[5] It has been sold online as anootropic.^[6]

References

[edit]

^^a ^b ^cLiu X, Chan CB, Jang SW, Pradoldej S, Huang J, He K, et al. (December 2010)."A synthetic 7,8-dihydroxyflavone derivative promotes neurogenesis and exhibits potent antidepressant effect".Journal of Medicinal Chemistry.53 (23):8274–86.doi:10.1021/jm101206p.PMC 3150605.PMID 21073191.
^Liu X, Chan CB, Qi Q, Xiao G, Luo HR, He X, Ye K (October 2012)."Optimization of a small tropomyosin-related kinase B (TrkB) agonist 7,8-dihydroxyflavone active in mouse models of depression".Journal of Medicinal Chemistry.55 (19):8524–37.doi:10.1021/jm301099x.PMC 3491656.PMID 22984948.
^^a ^b ^cLiu C, Chan CB, Ye K (2016)."7,8-dihydroxyflavone, a small molecular TrkB agonist, is useful for treating various BDNF-implicated human disorders".Translational Neurodegeneration.5 (1) 2.doi:10.1186/s40035-015-0048-7.PMC 4702337.PMID 26740873.
^^a ^bZeng Y, Wang X, Wang Q, Liu S, Hu X, McClintock SM (November 2013). "Small molecules activating TrkB receptor for treating a variety of CNS disorders".CNS & Neurological Disorders Drug Targets.12 (7):1066–77.doi:10.2174/18715273113129990089.PMID 23844685.
^Jiang M, Peng Q, Liu X, Jin J, Hou Z, Zhang J, et al. (June 2013)."Small-molecule TrkB receptor agonists improve motor function and extend survival in a mouse model of Huntington's disease".Human Molecular Genetics.22 (12):2462–70.doi:10.1093/hmg/ddt098.PMC 3658168.PMID 23446639.
^"Эутропофлавин (4'-DMA-7,8-DHF)".АИПСИН (in Russian). Retrieved1 January 2026.

Flavones and their conjugates

Aglycones

Monohydroxyflavone	3-Hydroxyflavone 6-Hydroxyflavone
Dihydroxyflavones	Chrysin 4',7-Dihydroxyflavone 7,8-Dihydroxyflavone
Trihydroxyflavones	Apigenin Baicalein Galangin Norwogonin 7,8,3'-Trihydroxyflavone 6,7,4'-Trihydroxyflavone
Tetrahydroxyflavones	Fisetin Kaempferol Isoscutellarein Luteolin Norartocarpetin Scutellarein
Pentahydroxyflavones	Herbacetin Morin Quercetin Nortangeretin 6-Hydroxyluteolin Norwightin Hypolaetin Tricetin
O-methylated flavones	4',7-Dihydroxy-6-methoxyflavone Acacetin Alnetin Artocarpetin Chrysoeriol Cirsilineol Cirsiliol Cirsimaritin Diosmetin Eupatilin Genkwanin Hispidulin Nepetin Nobiletin Oroxylin A Pratol Salvigenin Sinensetin Tangeretin Techtochrysin Tricin Wogonin Zapotin

Glycosides

of apigenin	Apiin Apigetrin Isovitexin Rhoifolin Saponarin Schaftoside Vicenin-2 Vitexin
of baicalein	Baicalin Tetuin
of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide
of luteolin	Cynaroside Isoorientin Orientin Veronicastroside Luteolin-7-O-glucuronide

Acetylated

Artocarpetin A

Artoindonesianin P

Sulfated glycosides

Theograndin I andII

Polymers

Drugs

Category

Growth factor receptor modulators

Angiopoietin

Agonists:Angiopoietin 1
Angiopoietin 4

Antagonists:Angiopoietin 2
Angiopoietin 3

Kinase inhibitors:Altiratinib
CE-245677
Rebastinib

Antibodies:Evinacumab (against angiopoietin 3)
Nesvacumab (against angiopoietin 2)

CNTF

EGF (ErbB)

EGF (ErbB1/HER1)	Agonists:Amphiregulin Betacellulin EGF (urogastrone) Epigen Epiregulin Heparin-binding EGF-like growth factor (HB-EGF) Murodermin Nepidermin Transforming growth factor alpha (TGFα) Kinase inhibitors:Afatinib Agerafenib Brigatinib Canertinib Dacomitinib Erlotinib Gefitinib Grandinin Icotinib Lapatinib Neratinib Osimertinib Vandetanib WHI-P 154 Antibodies:Cetuximab Depatuxizumab Depatuxizumab mafodotin Futuximab Imgatuzumab Matuzumab Necitumumab Nimotuzumab Panitumumab Zalutumumab
ErbB2/HER2	Agonists:Unknown/none Antibodies:Ertumaxomab Pertuzumab Trastuzumab Trastuzumab deruxtecan Trastuzumab duocarmazine Trastuzumab emtansine Kinase inhibitors:Afatinib Lapatinib Mubritinib Neratinib Tucatinib
ErbB3/HER3	Agonists:Neuregulins (heregulins) (1,2,6 (neuroglycan C)) Antibodies:Duligotumab Patritumab Seribantumab
ErbB4/HER4	Agonists:Betacellulin Epigen Heparin-binding EGF-like growth factor (HB-EGF) Neuregulins (heregulins) (1,2,3,4,5 (tomoregulin, TMEFF))

FGF

FGFR1	Agonists:Ersofermin FGF (1,2 (bFGF),3,4,5,6,8,10 (KGF2),20) Repifermin Selpercatinib Trafermin Velafermin
FGFR2	Agonists:Ersofermin FGF (1,2 (bFGF),3,4,5,6,7 (KGF),8,9,10 (KGF2),17,18,22) Palifermin Repifermin Selpercatinib Sprifermin Trafermin Antibodies:Aprutumab Aprutumab ixadotin Kinase inhibitors:Infigratinib
FGFR3	Agonists:Ersofermin FGF (1,2 (bFGF),4,8,9,18,23) Selpercatinib Sprifermin Trafermin Antibodies:Burosumab (against FGF23)
FGFR4	Agonists:Ersofermin FGF (1,2 (bFGF),4,6,8,9,19) Trafermin
Unsorted	Agonists:FGF15/19

HGF (c-Met)

Agonists:Fosgonimeton
Hepatocyte growth factor

Potentiators:Dihexa (PNB-0408)

IGF

IGF-1	Agonists:des(1-3)IGF-1 Insulin-like growth factor-1 (somatomedin C) IGF-1 LR3 Insulin-like growth factor-2 (somatomedin A) Insulin Mecasermin Mecasermin rinfabate Kinase inhibitors:BMS-754807 Linsitinib NVP-ADW742 NVP-AEW541 OSl-906 Antibodies:AVE-1642 Cixutumumab Dalotuzumab Figitumumab Ganitumab Robatumumab R1507 Teprotumumab Xentuzumab (against IGF-1 and IGF-2)
IGF-2	Agonists:Insulin-like growth factor-2 (somatomedin A) Antibodies:Dusigitumab Xentuzumab (against IGF-1 and IGF-2)
Others	Binding proteins:IGFBP (1,2,3,4,5,6,7) Cleavage products/derivatives with unknown target:Glypromate (GPE, (1-3)IGF-1) Trofinetide

LNGF (p75^NTR)

Antibodies:Against NGF:ABT-110 (PG110)
ASP-6294
Fasinumab
Frunevetmab
Fulranumab
MEDI-578
Ranevetmab
Tanezumab

Aptamers:Against NGF:RBM-004

Decoy receptors:LEVI-04 (p75^NTR-Fc)

PDGF

Agonists:Becaplermin
Platelet-derived growth factor (A,B,C,D)

RET (GFL)

GFRα1	Agonists:Glial cell line-derived neurotrophic factor (GDNF) Liatermin Kinase inhibitors:Vandetanib
GFRα2	Agonists:Neurturin (NRTN) Kinase inhibitors:Vandetanib
GFRα3	Agonists:Artemin (ARTN) Kinase inhibitors:Vandetanib
GFRα4	Agonists:Persephin (PSPN) Kinase inhibitors:Vandetanib
Unsorted	Kinase inhibitors:Agerafenib

SCF (c-Kit)

Agonists:Ancestim
Stem cell factor

TGFβ

Seehere instead.

Trk

TrkA	Agonists:Amitriptyline BNN-20 BNN-27 Cenegermin DHEA DHEA-S Gambogic amide NGF Tavilermide Antagonists:ALE-0540 Dexamethasone FX007 Testosterone Positive allosteric modulators:ACD856 ACD857 Ponazuril (ACD855) Toltrazuril Negative allosteric modulators:VM-902A Kinase inhibitors:Altiratinib AZD-6918 CE-245677 CH-7057288 DS-6051 Entrectinib GZ-389988 K252a Larotrectinib Lestaurtinib Milciclib ONO-4474 ONO-5390556 PLX-7486 Rebastinib SNA-120 (pegylated K252a)) Antibodies:Against TrkA:GBR-900;Against NGF:ABT-110 (PG110) ASP-6294 Fasinumab Frunevetmab Fulranumab MEDI-578 Ranevetmab Tanezumab Aptamers:Against NGF:RBM-004 Decoy receptors:ReN-1820 (TrkAd5)
TrkB	Agonists:3,7-DHF 3,7,8,2'-THF 4'-DMA-7,8-DHF 7,3'-DHF 7,8-DHF 7,8,2'-THF 7,8,3'-THF Amitriptyline Braegen-02 BDNF BNN-20 Deoxygedunin Diosmetin DMAQ-B1 HIOC LM22A-4 N-Acetylserotonin NT-3 NT-4 Norwogonin (5,7,8-THF) R7 R13 (BrAD-R13, Braegen-01) TDP6 Antagonists:ANA-12 Cyclotraxin B Gossypetin (3,5,7,8,3',4'-HHF) Ligands:DHEA Positive allosteric modulators:ACD856 ACD857 Ponazuril (ACD855) Toltrazuril Kinase inhibitors:Altiratinib AZD-6918 CE-245677 CH-7057288 DS-6051 Entrectinib GZ-389988 K252a Larotrectinib Lestaurtinib ONO-4474 ONO-5390556 PLX-7486
TrkC	Agonists:BNN-20 DHEA NT-3 Positive allosteric modulators:ACD856 Kinase inhibitors:Altiratinib AZD-6918 CE-245677 CH-7057288 DS-6051 Entrectinib GZ-389988 K252a Larotrectinib Lestaurtinib ONO-4474 ONO-5390556 PLX-7486