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Purmorphamine is a 2,6,9-trisubstituted purine that promotes osteoblast differentiation and activates the Hedgehog signaling pathway by targeting the 7-transmembrane Smo receptor. It is a light tan solid and has potential therapeutic applications for bone diseases such as osteoporosis.

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  • 9-cyclohexyl-N-(4-morpholin-4-ylphenyl)-2-naphthalen-1-yloxypurin-6-amine

    Cas No: 483367-10-8

  • USD $ 1.9-2.9 / Gram

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  • 483367-10-8 Structure
  • Basic information

    1. Product Name: Purmorphamine
    2. Synonyms: 2-(1-NAPHTHOXY)-6-(4-MORPHOLINOANILINO)-9-CYCLOHEXYLPURINE;PURMORPHAMINE;9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine;9-Cyclohexyl-N-[(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine;9-Cyclohexyl-N-[4-(Morpholin-4-yl)phenyl]-2-(naphthalen-1-yloxy)-9H-purin-6-aMine;9-Cyclohexyl-N-[4-(4-Morpholinyl)phenyl]-2-(1-naphthalenyloxy)-;9H-Purin-6-amine, 9-cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-;9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine Purmorphamine
    3. CAS NO:483367-10-8
    4. Molecular Formula: C31H32N6O2
    5. Molecular Weight: 520.62478
    6. EINECS: 200-256-5
    7. Product Categories: Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Lipid signaling;Inhibitors
    8. Mol File: 483367-10-8.mol
  • Chemical Properties

    1. Melting Point: 210-212°C
    2. Boiling Point: 790.313 °C at 760 mmHg
    3. Flash Point: 431.766 °C
    4. Appearance: white to beige/
    5. Density: 1.353 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: -20°C Freezer
    8. Solubility: DMSO: soluble5mg/mL, clear (warmed)
    9. PKA: 5.44±0.40(Predicted)
    10. 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.
    11. CAS DataBase Reference: Purmorphamine(CAS DataBase Reference)
    12. NIST Chemistry Reference: Purmorphamine(483367-10-8)
    13. EPA Substance Registry System: Purmorphamine(483367-10-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 483367-10-8(Hazardous Substances Data)

483367-10-8 Usage

Uses

Used in Pharmaceutical Industry:
Purmorphamine is used as an activator of the hedgehog (Hh) signaling pathway for promoting osteoblast differentiation, which might be useful as a therapeutic agent for bone diseases such as osteoporosis.
Used in Research Applications:
Purmorphamine is used as a research tool for studying the consequences of upregulation of the Hedgehog signaling pathway, particularly in Tupfel long fin strain Zebrafish.
Used in Drug Development:
Purmorphamine is used as a chemical compound to activate the Hedgehog pathway by targeting Smoothened, which can be beneficial in the development of drugs targeting this pathway for various therapeutic applications.

Biochem/physiol Actions

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.

in vitro

purmorphamine activated the hedgehog pathway by directly bound and activated smoothened with the ic50value of ~ 1.5 μm in competing with cyclopamine, a smo antagonist [1]. in multi-potent c3h10t1/2 cells, purmorphamine was a potent inducer of osteogenesis. in c3h10t1/2 cells, the ec50 values assessed based on alp expression for purmorphamine was 1 μm. purmorphamine (1 μm) in combination with bmp-4 (100 ng/ml) increased alp activity more than 90-fold in 3t3-l1 cells [3].administration of purmorphamine at 3 and 5 μm up-regulated the level of osteocalcin on day 14 (p ≤ 0.05)[4].

in vivo

in rats transplanted with stem cell-based constructs subcutaneously, treatment with purmorphamine tended to up-regulate alp transcripts when compared with those injected by either dexamethasone or injection water (p ≤ 0.05) [4].

References

1) Wu et al. (2002), A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells; J. Am. Chem. Soc., 124 14520 2) Wu et al. (2004), Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway; Chem. Biol. 11 1229 3) Sinha and Chen (2006), Purmorphamine activates the Hedgehog pathway by targeting Smoothened; Nat. Chem. Biol., 2 29 4) Kang et al. (2015), Reprogramming of mouse somatic cells into pluripotent stem-like cells using a combination of small molecules; Biomaterials, 35 7336 5) Zhang et al. (2015), Small Molecules Efficiently Reprogram Human Astroglial Cells into Functional Neurons; Cell Stem Cell 17 735

Check Digit Verification of cas no

The CAS Registry Mumber 483367-10-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,8,3,3,6 and 7 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 483367-10:
(8*4)+(7*8)+(6*3)+(5*3)+(4*6)+(3*7)+(2*1)+(1*0)=168
168 % 10 = 8
So 483367-10-8 is a valid CAS Registry Number.

483367-10-8 Well-known Company Product Price

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  • Sigma

  • (SML0868)  Purmorphamine  ≥98% (HPLC)

  • 483367-10-8

  • SML0868-5MG

  • 1,232.01CNY

  • Detail
  • Sigma

  • (SML0868)  Purmorphamine  ≥98% (HPLC)

  • 483367-10-8

  • SML0868-25MG

  • 4,966.65CNY

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483367-10-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Purmorphamine

1.2 Other means of identification

Product number -
Other names 2-(1-Naphthoxy)-6-(4-morpholinoanilino)-9-cyclohexylpurine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:483367-10-8 SDS

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