Dorsomorphin free base
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MedKoo CAT#: 406557

CAS#: 866405-64-3 (free base)

Description: Dorsomorphin, also known as BML-275 , is a selective small molecule inhibitor of BMP signaling, which promotes cardiomyogenesis in embryonic stem cells. Dorsomorphin reverses the mesenchymal phenotype of breast cancer initiating cells by inhibition of bone morphogenetic protein signaling.


Chemical Structure

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Dorsomorphin free base
CAS# 866405-64-3 (free base)

Theoretical Analysis

MedKoo Cat#: 406557
Name: Dorsomorphin free base
CAS#: 866405-64-3 (free base)
Chemical Formula: C24H25N5O
Exact Mass: 399.2059
Molecular Weight: 399.5
Elemental Analysis: C, 72.16; H, 6.31; N, 17.53; O, 4.00

Price and Availability

Size Price Availability Quantity
100.0mg USD 650.0 2 weeks
200.0mg USD 1150.0 2 weeks
500.0mg USD 1950.0 2 weeks
1.0g USD 2950.0 2 weeks
2.0g USD 4950.0 2 weeks
5.0g USD 9850.0 2 weeks
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Related CAS #: 1219168-18-9 (HCl)   866405-64-3 (free base)  

Synonym: Dorsomorphin; Compound C; BML275; BML-275; BML 275; CpdC

IUPAC/Chemical Name: 6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

InChi Key: XHBVYDAKJHETMP-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H25N5O/c1-2-12-28(13-3-1)14-15-30-22-6-4-19(5-7-22)21-16-26-24-23(17-27-29(24)18-21)20-8-10-25-11-9-20/h4-11,16-18H,1-3,12-15H2

SMILES Code: C12=C(C3=CC=NC=C3)C=NN1C=C(C4=CC=C(OCCN5CCCCC5)C=C4)C=N2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 399.5 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Valizadeh-Arshad Z, Shahbazi E, Hashemizadeh S, Moradmand A, Jangkhah M, Kiani S. In Vitro Differentiation of Neural-Like Cells from Human Embryonic Stem Cells by A Combination of Dorsomorphin, XAV939, and A8301. Cell J. 2018 Jan;19(4):545-551. doi: 10.22074/cellj.2018.4232. Epub 2017 Nov 4. PubMed PMID: 29105388; PubMed Central PMCID: PMC5672092.

2: Łabuzek K, Liber S, Gabryel B, Bułdak Ł, Okopień B. Erratum to: Ambivalent effects of compound C (dorsomorphin) on inflammatory response in LPS-stimulated rat primary microglial cultures. Naunyn Schmiedebergs Arch Pharmacol. 2017 Mar;390(3):327-328. doi: 10.1007/s00210-017-1348-5. PubMed PMID: 28160017.

3: Lin T, Wang XL, Zettervall SL, Cai Y, Guzman RJ. Dorsomorphin homologue 1, a highly selective small-molecule bone morphogenetic protein inhibitor, suppresses medial artery calcification. J Vasc Surg. 2017 Aug;66(2):586-593. doi: 10.1016/j.jvs.2016.03.462. Epub 2016 Jun 30. PubMed PMID: 27374065; PubMed Central PMCID: PMC5201454.

4: Madhu V, Dighe AS, Cui Q, Deal DN. Dual Inhibition of Activin/Nodal/TGF-β and BMP Signaling Pathways by SB431542 and Dorsomorphin Induces Neuronal Differentiation of Human Adipose Derived Stem Cells. Stem Cells Int. 2016;2016:1035374. doi: 10.1155/2016/1035374. Epub 2015 Dec 20. PubMed PMID: 26798350; PubMed Central PMCID: PMC4699250.

5: Horbelt D, Boergermann JH, Chaikuad A, Alfano I, Williams E, Lukonin I, Timmel T, Bullock AN, Knaus P. Small molecules dorsomorphin and LDN-193189 inhibit myostatin/GDF8 signaling and promote functional myoblast differentiation. J Biol Chem. 2015 Feb 6;290(6):3390-404. doi: 10.1074/jbc.M114.604397. Epub 2014 Nov 3. PubMed PMID: 25368322; PubMed Central PMCID: PMC4319009.

6: Ali JL, Lagasse BJ, Minuk AJ, Love AJ, Moraya AI, Lam L, Arthur G, Gibson SB, Morrison LC, Werbowetski-Ogilvie TE, Fu Y, Nachtigal MW. Differential cellular responses induced by dorsomorphin and LDN-193189 in chemotherapy-sensitive and chemotherapy-resistant human epithelial ovarian cancer cells. Int J Cancer. 2015 Mar 1;136(5):E455-69. doi: 10.1002/ijc.29220. Epub 2014 Sep 26. PubMed PMID: 25227893.

7: Garulli C, Kalogris C, Pietrella L, Bartolacci C, Andreani C, Falconi M, Marchini C, Amici A. Dorsomorphin reverses the mesenchymal phenotype of breast cancer initiating cells by inhibition of bone morphogenetic protein signaling. Cell Signal. 2014 Feb;26(2):352-62. doi: 10.1016/j.cellsig.2013.11.022. Epub 2013 Nov 23. PubMed PMID: 24280125.

8: Wong TT, Collodi P. Dorsomorphin promotes survival and germline competence of zebrafish spermatogonial stem cells in culture. PLoS One. 2013 Aug 1;8(8):e71332. doi: 10.1371/journal.pone.0071332. Print 2013. PubMed PMID: 23936500; PubMed Central PMCID: PMC3731312.

9: Engers DW, Frist AY, Lindsley CW, Hong CC, Hopkins CR. Synthesis and structure-activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of dorsomorphin: the discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe. Bioorg Med Chem Lett. 2013 Jun 1;23(11):3248-52. doi: 10.1016/j.bmcl.2013.03.113. Epub 2013 Apr 11. PubMed PMID: 23639540; PubMed Central PMCID: PMC3677712.

10: Karthikeyan K, Mahat MY, Chandrasekaran S, Gopal K, Franklin PX, Sivakumar BJ, Singh G, Narayanan S, Gopalan B, Khan AA. Bioanalytical method development, validation and quantification of dorsomorphin in rat plasma by LC-MS/MS. Biomed Chromatogr. 2013 Aug;27(8):1018-26. doi: 10.1002/bmc.2899. Epub 2013 Mar 21. PubMed PMID: 23526253.

11: Kudo TA, Kanetaka H, Mizuno K, Ryu Y, Miyamoto Y, Nunome S, Zhang Y, Kano M, Shimizu Y, Hayashi H. Dorsomorphin stimulates neurite outgrowth in PC12 cells via activation of a protein kinase A-dependent MEK-ERK1/2 signaling pathway. Genes Cells. 2011 Nov;16(11):1121-32. doi: 10.1111/j.1365-2443.2011.01556.x. Epub 2011 Oct 12. PubMed PMID: 21988724.

12: Gonzalez R, Lee JW, Snyder EY, Schultz PG. Dorsomorphin promotes human embryonic stem cell self-renewal. Angew Chem Int Ed Engl. 2011 Apr 4;50(15):3439-41. doi: 10.1002/anie.201005659. Epub 2011 Mar 7. PubMed PMID: 21384475.

13: Boergermann JH, Kopf J, Yu PB, Knaus P. Dorsomorphin and LDN-193189 inhibit BMP-mediated Smad, p38 and Akt signalling in C2C12 cells. Int J Biochem Cell Biol. 2010 Nov;42(11):1802-7. doi: 10.1016/j.biocel.2010.07.018. Epub 2010 Aug 5. PubMed PMID: 20691279.

14: Hao J, Ho JN, Lewis JA, Karim KA, Daniels RN, Gentry PR, Hopkins CR, Lindsley CW, Hong CC. In vivo structure-activity relationship study of dorsomorphin analogues identifies selective VEGF and BMP inhibitors. ACS Chem Biol. 2010 Feb 19;5(2):245-53. doi: 10.1021/cb9002865. PubMed PMID: 20020776; PubMed Central PMCID: PMC2825290.

15: Suenaga M, Matsui T, Funaba M. BMP Inhibition with dorsomorphin limits adipogenic potential of preadipocytes. J Vet Med Sci. 2010 Mar;72(3):373-7. Epub 2009 Dec 8. PubMed PMID: 19996563.

16: Labuzek K, Liber S, Gabryel B, Bułdak L, Okopień B. Ambivalent effects of compound C (dorsomorphin) on inflammatory response in LPS-stimulated rat primary microglial cultures. Naunyn Schmiedebergs Arch Pharmacol. 2010 Jan;381(1):41-57. doi: 10.1007/s00210-009-0472-2. Epub 2009 Nov 26. Erratum in: Naunyn Schmiedebergs Arch Pharmacol. 2017 Feb 4;:. Naunyn Schmiedebergs Arch Pharmacol. 2017 Mar;390(3):327-328. PubMed PMID: 19940979.

17: Hao J, Daleo MA, Murphy CK, Yu PB, Ho JN, Hu J, Peterson RT, Hatzopoulos AK, Hong CC. Dorsomorphin, a selective small molecule inhibitor of BMP signaling, promotes cardiomyogenesis in embryonic stem cells. PLoS One. 2008 Aug 6;3(8):e2904. doi: 10.1371/journal.pone.0002904. PubMed PMID: 18682835; PubMed Central PMCID: PMC2483414.

18: Yu PB, Hong CC, Sachidanandan C, Babitt JL, Deng DY, Hoyng SA, Lin HY, Bloch KD, Peterson RT. Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism. Nat Chem Biol. 2008 Jan;4(1):33-41. Epub 2007 Nov 18. PubMed PMID: 18026094; PubMed Central PMCID: PMC2727650.



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