:Purmorphamine
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = 9-cyclohexyl-N-(4-morpholinophenyl)-2-(naphthalen-1-yloxy)-9H-purin-6-amine
| image = Purmorphamine_structure.png
| width = 260
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| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 483367-10-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PB12M2F8KY
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| PubChem = 5284329
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| ChemSpiderID = 4447411
| C=31 | H=32 | N=6 | O=2
| smiles = C1(N(C2CCCCC2)C=N3)=C3C(NC4=CC=C(N5CCOCC5)C=C4)=NC(OC6=CC=CC7=C6C=CC=C7)=N1
| StdInChI = 1S/C31H32N6O2/c1-2-9-25(10-3-1)37-21-32-28-29(33-23-13-15-24(16-14-23)36-17-19-38-20-18-36)34-31(35-30(28)37)39-27-12-6-8-22-7-4-5-11-26(22)27/h4-8,11-16,21,25H,1-3,9-10,17-20H2,(H,33,34,35)
| StdInChIKey = FYBHCRQFSFYWPY-UHFFFAOYSA-N
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Purmorphamine was the first small-molecule agonist developed for the protein Smoothened, a key part of the hedgehog signaling pathway, which is involved in bone growth, cardiovascular regeneration and brain development as well as having a number of other functions in the body. Purmorphamine has been shown to induce osteogenesis in bone tissue as well as influencing growth and differentiation of neurons in the brain.{{cite journal | vauthors = Wu X, Ding S, Ding Q, Gray NS, Schultz PG | title = A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells | journal = Journal of the American Chemical Society | volume = 124 | issue = 49 | pages = 14520–1 | date = December 2002 | pmid = 12465946 | doi = 10.1021/ja0283908 }}{{cite journal | vauthors = Wu X, Walker J, Zhang J, Ding S, Schultz PG | title = Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway | journal = Chemistry & Biology | volume = 11 | issue = 9 | pages = 1229–38 | date = September 2004 | pmid = 15380183 | doi = 10.1016/j.chembiol.2004.06.010 | doi-access = free }}{{cite journal | vauthors = Sinha S, Chen JK | s2cid = 29035911 | title = Purmorphamine activates the Hedgehog pathway by targeting Smoothened | journal = Nature Chemical Biology | volume = 2 | issue = 1 | pages = 29–30 | date = January 2006 | pmid = 16408088 | doi = 10.1038/nchembio753 }}{{cite journal | vauthors = Lee SJ, Lee HK, Cho SY, Choi JK, Shin HK, Kwak EJ, Cho MR, Kim HR, Kim SR, Kim YM, Park KJ, Choi JK | display-authors = 6 | title = Identification of osteogenic purmorphamine derivatives | journal = Molecules and Cells | volume = 26 | issue = 4 | pages = 380–6 | date = October 2008 | pmid = 18695357 }}{{cite journal | vauthors = Stanton BZ, Peng LF | title = Small-molecule modulators of the Sonic Hedgehog signaling pathway | journal = Molecular BioSystems | volume = 6 | issue = 1 | pages = 44–54 | date = January 2010 | pmid = 20024066 | doi = 10.1039/b910196a }}{{cite journal | vauthors = Aravamudhan A, Ramos DM, Nip J, Subramanian A, James R, Harmon MD, Yu X, Kumbar SG | display-authors = 6 | title = Osteoinductive small molecules: growth factor alternatives for bone tissue engineering | journal = Current Pharmaceutical Design | volume = 19 | issue = 19 | pages = 3420–8 | year = 2013 | pmid = 23432678 | doi = 10.2174/1381612811319190008 }}
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