6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE

Background

Product Name: 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE
CAS No.: 866405-64-3
Chemical Name: 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE
Synonyms: Dorsomorphin;COMPOUND C;BML-275;DORSOMORPHIN 2HCL;BML-275HCL;Dorsomorphin dihydrochloride;CS-1075;AMPK INHIBITOR;Dorsomorphin, 98%+;dorsoMorphin (BML-275)
CBNumber: CB8786803
Molecular Formula: C24H25N5O
Formula Weight: 399.49
MOL File: 866405-64-3.mol

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6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Property

Melting point:: >228°C(dec.)
Density: 1.25±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO: >2mg/mL (warmed)
pka: 8.53±0.10(Predicted)
form: powder
color: white to beige
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI: 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
InChIKey: XHBVYDAKJHETMP-UHFFFAOYSA-N
SMILES: C12=C(C3C=CN=CC=3)C=NN1C=C(C1=CC=C(OCCN3CCCCC3)C=C1)C=N2

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22
Safety Statements: 36/37
WGK Germany: 3
HS Code: 2933599590

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 171260
Product name: AMPK Inhibitor, Compound C
Packaging: 1mg
Price: $141
Updated: 2025/07/31

Sigma-Aldrich

Product number: 171260
Product name: AMPK Inhibitor, Compound C
Packaging: 5mg
Price: $402
Updated: 2025/07/31

TCI Chemical

Product number: D5394
Product name: Dorsomorphin
Purity: >97.0%(HPLC)
Packaging: 10mg
Price: $211
Updated: 2025/07/31

TCI Chemical

Product number: D5394
Product name: Dorsomorphin
Purity: >97.0%(HPLC)
Packaging: 50mg
Price: $634
Updated: 2025/07/31

Cayman Chemical

Product number: 11967
Product name: Dorsomorphin
Purity: ≥98%
Packaging: 5mg
Price: $57
Updated: 2024/03/01

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6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Chemical Properties,Usage,Production

Description

Dorsomorphin (866405-64-3) is a potent, selective and ATP-competitive inhibitor of AMP-activated protein kinase (AMPK) (Ki = 109 nM).1 It displays no significant inhibition of ZAPK, SYK, PKCT, PKA and JAK3. It inhibits bone morphogenetic protein (BMP) type I receptors (ALK2, ALK3 and ALK6).2 Dorsomorphin has been shown to promote cardiomyogenesis in mouse embryonic stem cells (ESCs) in vitro.3 Dorsomorphin also induces autophagy in cancer cell lines via a mechanism independent of AMPK inhibition.4

Uses

Dorsomorphin has been used:

as an inhibitor of adenosine monophosphate-activated protein kinase (AMPK) to find the effects of trans-resveratrol on lipid mobilization in 3T3-L1 (a murine cell line of adipocytes) cells
as an AMPK inhibitor, to indicate the involvement of AMPK/mTOR (mammalian target of rapamycin) pathway in LRG (liraglutide) -induced autophagy
in the induction step, employed in in vitro differentiation of Friedreich′s ataxia (FRDA) and induced pluripotent stem cells (iPSCs) to neurospheres and neurons using ES (embryonic stem cell) media

Uses

A potent inhibitor of AMPK and fatty acid biosynthesis.

Definition

ChEBI: A pyrazolopyrimidine that is pyrazolo[1,5-a]pyrimidine which is substituted at positions 3 and 6 by pyridin-4-yl and p-[2-(piperidin-1-yl)ethoxy]phenyl groups, respectively. It is a potent, selective, reversible, and ATP-competiti e inhibitor of AMPK (AMP-activated protein kinase, EC 2.7.11.31) and a selective inhibitor of bone morphogenetic protein (BMP) signaling.

General Description

A cell-permeable pyrrazolopyrimidine compound that inhibits against KDR/VEGFR2, ALK2/BMPR-I, AMPK kinase activity (IC₅₀ = 25.1, 148, and 234.6 nM, respectively), while exhibiting much reduced or little effect toward ALK5/TGFβR-I, ZAPK, Syk, PKCθ, PKA, or JAK3. Shown to block both BMP pathway-dependent dorsoventral development (EC₁₀₀ = 2.5 μM) and VEGF signaling-dependent intersomitic vessel formation (EC₅₀ = 5 μM) in zebrafish embryo in vivo. Commonly used in combination with AMPK activators AICAR (Cat. No. 123040) and/or Metformin (Cat. No. 317240) for studying AMPK-dependent cellular events in vitro and physiological responses in animals in vivo.

Biological Activity

Potent and selective inhibitor of AMP-activated protein kinase (AMPK) (K i = 109 nM). Displays no significant activity on several structurally related kinases including ZAPK, SYK, PKC θ , PKA and JAK3. Inhibits AMPK activation induced by AICAR and metformin. Also inhibits bone morphogenic protein (BMP) type I receptors (ALK2, ALK3 and ALK6). Promotes cardiomyogenesis in mouse embryonic stem cells (ESCs) in vitro .

Biochem/physiol Actions

Target IC50: 25.1, 148, and 234.6 nM, against KDR/VEGFR2, ALK2/BMPR-I, AMPK kinase activity, respectively

Background

Dorsomorphin is a potent and reversible AMP-activated protein kinase inhibitor that competes with ATP in the absence of AMP with a Ki value of 109 nM. This small compound is selective, displaying no significant inhibition of other kinases inclusive of ZAPK, SYK, PKCθ, PKA, and JAK3. Research has shown that Dorsomorphin inhibits tumor cell proliferation and induces apoptosis through mechanisms independent of the AMPK pathway. This compound inhibits the effects that AICAR and metformin have on inactivating acetyl-CoA carboxylase and selectively inhibits the BMP type I receptors ALK2, ALK3, and ALK6.

References

[1] ZHOU G, MYERS R W, LI Y, et al. Role of AMP-activated protein kinase in mechanism of metformin action.[J]. The Journal of clinical investigation, 2001, 1 1: 0. DOI:10.1172/jci13505
[2] PAUL B YU. Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism[J]. Nature chemical biology, 2007, 4 1: 33-41. DOI:10.1038/nchembio.2007.54
[3] JIJUN HAO. Dorsomorphin, a selective small molecule inhibitor of BMP signaling, promotes cardiomyogenesis in embryonic stem cells.[J]. PLoS ONE, 2008, 3 8: e2904. DOI:10.1371/journal.pone.0002904
[4] LJUBICA VUCICEVIC. Compound C induces protective autophagy in cancer cells through AMPK inhibition-independent blockade of Akt/mTOR pathway.[J]. Autophagy, 2011, 7 1: 40-50. DOI:10.4161/auto.7.1.13883

6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE Suppliers

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View Lastest Price from 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE manufacturers

Career Henan Chemical Co

Product: 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE 866405-64-3
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 25kg
Release date: 2019-07-11

866405-64-3, 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINERelated Search:

STF-62247 Chloroquine diphosphate Thapsigargin Itraconazole FETAL BOVINE SERUM USA ORIGIN 6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE 4-(4-Pyridinyl)-1H-pyrazol-3-aMine Ampk Inhibitor

AMPK INHIBITOR

6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE

COMPOUND C

AMPK Inhibitor, Compound C, Dorsomorphin

InSolution AMPK Inhibitor, Compound C - CAS 866405-64-3 - Calbiochem

InSolution AMPK Inhibitor, Compound C2HCl - CAS 866405-64-3 - Calbiochem

AMPK Inhibitor, Compound C - CAS 866405-64-3 - Calbiochem

CS-1075

BML-275

Dorsomorphin

6-[4-[2-(1-Piperidinyl)ethoxy]phenyl]-3-(4-pyridinyl)-pyrazolo[1,5-a]pyrimidinedihydrochloride

Dorsomorphin dihydrochloride

DORSOMORPHIN 2HCL

Pyrazolo[1,5-a]pyriMidine, 6-[4-[2-(1-piperidinyl)ethoxy]phenyl]-3-(4-pyridinyl)-

DorsoMorphin, Free Base, >99%

6-(4-(2-(Piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrrazolo[1,5-a]pyrimidine

6-[4-[2-(1-piperidinyl)ethoxy]phenyl]-3-(4-pyridinyl)-pyrazolo[1,5-a]pyrimidine

InSolution? AMPK Inhibitor, Compound C

AMPK Inhibitor, Compound C

InSolution? AMPK Inhibitor, Compound C?2HCl

dorsoMorphin (BML-275)

DorsoMorphin (CoMpound C)

DORSOMORPHIN(COMPOUND C; BML-275)

BML-275HCL

BML-275(Dorsomorphin )

6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(yridine-4-yl)pyrazolo[1,5-a]pyrimidine

Dorsomorphin (Compound C) (DMSO solution)

Dorsomorphin, 98%+

AMP-activated protein kinase,inhibit,ATP-competitive,Dorsomorphin,BML 275,Inhibitor,BMP,Transforming growth factor beta receptors,Autophagy,AMPK,type,receptors,BML275,TGF-β Receptor

Dorsomorphin (Compound C) (DMSO solution), AMP-kinase inhibitor

Dorsomorphin (Compound C), AMP-kinase inhibitor

AMPK Inhibitor, Compound C?2HCl

Dorsomorphin (Synonyms: Compound C

866405-64-3

C24H25N5O2HCl

Inhibitors