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Merck

SML0868

Purmorphamine

≥98% (HPLC), powder, Hedgehog signaling activator

Synonym(s):

2-(1-Naphthoxy)-6-(4-morpholinoanilino)-9-cyclohexylpurine; 9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-

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About This Item

Empirical Formula (Hill Notation):
C31H32N6O2
CAS Number:
483367-10-8
Molecular Weight:
520.62
UNSPSC Code:
51111800
NACRES:
NA.77

Key Documents

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Product Name

Purmorphamine, ≥98% (HPLC)

SMILES string

N7(CCOCC7)c1ccc(cc1)Nc2nc(nc5[n](cnc52)C6CCCCC6)Oc3c4c(ccc3)cccc4

InChI

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)

InChI key

FYBHCRQFSFYWPY-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

Quality Level

100

Application

Purmorphamine has been used to study the consequences of upregulation of Hedgehog signalling pathway in Tupfel long fin strain Zebrafish.

Biochem/physiol Actions

Purmorphamine activates the Hedgehog (Hh) signaling pathway, directly binding to the Smoothened (Smo) receptor.
Purmorphamine activates the Hedgehog (Hh) signaling pathway, directly binding to the Smoothened (Smo) receptor. In various studies, purmorphamine has been shown to induce osteoblast differentiation, generate cardiomyocytes from human embryonic stem cells, increase the neuronal differentiation of a human striatal neural stem cell line, and to differentiate human umbilical cord mesenchymal stem cells (hUCMSCs) into motoneurons.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H341

Hazard Classifications

Muta. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
126M4767V
016M4755V
065M4721V
014M4707V

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Shabana Amanda Ali et al.
Arthritis & rheumatology (Hoboken, N.J.), 68(1), 127-137 (2015-09-01)
With no effective therapies to attenuate cartilage degeneration in osteoarthritis (OA), the result is pain and disability. Activation of hedgehog (HH) signaling causes changes related to the progression of OA, with higher levels of Gli-mediated transcriptional activation associated with increased
Sara Brilha et al.
Scientific reports, 7(1), 16031-16031 (2017-11-24)
Central nervous system tuberculosis (CNS TB) has a high mortality and morbidity associated with severe inflammation. The blood-brain barrier (BBB) protects the brain from inflammation but the mechanisms causing BBB damage in CNS TB are uncharacterized. We demonstrate that Mycobacterium
Methylation microarray studies highlight PDGFA expression as a factor in biliary atresia.
Cofer Z C, et al.
PLoS ONE, 11(3), e0151521-e0151521 (2016)
Roberto Simone et al.
EMBO molecular medicine, 10(1), 22-31 (2017-11-09)
Intronic GGGGCC repeat expansions in
Anna Drannik et al.
PloS one, 12(2), e0171668-e0171668 (2017-02-09)
Sonic hedgehog (Shh) is a morphogen essential to the developing nervous system that continues to play an important role in adult life by contributing to cell proliferation and differentiation, maintaining blood-brain barrier integrity, and being cytoprotective against oxidative and excitotoxic
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