Cas no 41941-56-4 (8-Chloroadenosine 3',5'-Cyclic Monophosphate)

8-Chloroadenosine 3',5'-Cyclic Monophosphate (8-Cl-cAMP) is a chemically modified derivative of cyclic adenosine monophosphate (cAMP), featuring a chlorine substitution at the 8-position of the adenine ring. This modification enhances its stability and resistance to phosphodiesterase-mediated degradation compared to native cAMP. 8-Cl-cAMP acts as a potent activator of protein kinase A (PKA) and exhibits selective modulation of PKA isozymes, making it a valuable tool for studying cAMP-dependent signaling pathways. Its improved membrane permeability and prolonged biological activity facilitate research in cell physiology, pharmacology, and cancer biology. The compound is widely utilized in mechanistic studies of cellular regulation and apoptosis.
8-Chloroadenosine 3',5'-Cyclic Monophosphate structure
41941-56-4 structure
Product Name:8-Chloroadenosine 3',5'-Cyclic Monophosphate
CAS No:41941-56-4
MF:C10H11ClN5O6P
MW:363.651001214981
CID:330138
PubChem ID:24892338
Update Time:2025-08-02

8-Chloroadenosine 3',5'-Cyclic Monophosphate Chemical and Physical Properties

Names and Identifiers

    • Adenosine, 8-chloro-,cyclic 3',5'-(hydrogen phosphate)
    • 8-CHLOROADENOSINE-CYCLIC -3',5'-MONOPHOSPHATE
    • 8-CHLORO-CAMP
    • 8-chloroadenosine 3',5'-cyclic-monophosphate
    • 8-chloroadenosine 3',5'-monophosphate
    • 8-chloro-cyclicadenosinemonophosphate
    • 8-chlorocyclicamp
    • 8-chloro-O3',O5'-hydroxyphosphoryl-adenosine
    • 8-CL-CAMP
    • Tocladesine
    • 8-Chloroadenosine 3′,5′-monophosphate
    • TOCLADESINE [USAN]
    • BQ94Z7E5OR
    • 8-Chloro-cyclic adenosine monophosphate
    • Adenosine, 8-chloro-, cyclic 3',5'-(hydrogen phosphate)
    • 8-chloro-cyclic AMP
    • CN1256
    • W-202723
    • Tocladesine (USAN/INN)
    • Q27274811
    • ADENAZOLE
    • CHEMBL2107085
    • SCHEMBL125595
    • NSC614491
    • NSC-614491
    • DTXSID101024678
    • CN 1256
    • DB13046
    • (4AR,6R,7R,7AS)-6-(6-AMINO-8-CHLORO-PURIN-9-YL)-2-OXO-TETRAHYDRO-2LAMBDA*5*-FURO(3,2-D)(1,3,2)DIOXAPHOSPHININE-2,7-DIOL
    • 6-(6-amino-8-chloropurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
    • CCRIS 846
    • NSC-284751
    • 41941-56-4
    • UNII-BQ94Z7E5OR
    • NSC 614491
    • HY-123396
    • 8-Chloroadenosine-cyclic-3',5'-monophosphate dihydrate
    • 8-chloroadenosine 3',5'-cyclic monophosphate
    • 8-Chloroadenosine-3',5'-O-monophosphate
    • 8-CHLOROADENOSINE-cyclic-3',5'-MONOPHOSPHATE
    • MFCD00153938
    • TOCLADESINE [INN]
    • NS00069841
    • Tocladesine [USAN:INN:BAN]
    • D06173
    • NCS 614491
    • ICN-1256
    • (4aR,6R,7R,7aS)-6-(6-amino-8-chloropurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
    • 8-CHLORO-CYCLIC ADENOSINE 3',5'-MONOPHOSPHATE
    • (4aR,6R,7R,7aS)-6-(6-amino-8-chloro-purin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
    • AKOS040749661
    • 8-Chloroadenosine 3',5'-cyclic phosphate
    • 4H-Furo[3,2-d]-1,3,2-dioxaphosphorin-7-ol, 6-(6-amino-8-chloro-9H-purin-9-yl)tetrahydro-2-hydroxy-, 2-oxide, (4aR,6R,7R,7aS)-
    • 8-CHLORO CYCLIC AMP
    • DA-70375
    • CLLFEJLEDNXZNR-UUOKFMHZSA-N
    • 8-Chloroadenosine 3',5'-Cyclic Monophosphate
    • MDL: MFCD00153938
    • Inchi: 1S/C10H11ClN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
    • InChI Key: CLLFEJLEDNXZNR-UUOKFMHZSA-N
    • SMILES: ClC1=NC2C(N)=NC=NC=2N1[C@H]1[C@@H]([C@H]2[C@@H](COP(=O)(O)O2)O1)O

Computed Properties

  • Exact Mass: 363.01400
  • Monoisotopic Mass: 363.0135478g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 10
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 1
  • Complexity: 532
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 4
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 3
  • XLogP3: -1.6
  • Topological Polar Surface Area: 155

Experimental Properties

  • Color/Form: Not determined
  • Density: 2.6±0.1 g/cm3
  • Boiling Point: 731.7±70.0 °C at 760 mmHg
  • Flash Point: 396.3±35.7 °C
  • Solubility: aqueous base: soluble
  • PSA: 164.65000
  • LogP: 0.41720
  • Solubility: Soluble
  • Vapor Pressure: 0.0±2.5 mmHg at 25°C

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8-Chloroadenosine 3',5'-Cyclic Monophosphate Suppliers

Amadis Chemical Company Limited
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(CAS:41941-56-4)8-Chloroadenosine 3',5'-Cyclic Monophosphate
Order Number:A1242868
Stock Status:in Stock
Quantity:1mg/5mg
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 19:24
Price ($):758/1895
NewCan Biotech Limited
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(CAS:41941-56-4)8-Chloroadenosine-cyclic-3',5'-monophosphatedihydrate
Order Number:NC12618
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Quantity:10g
Purity:97%
Pricing Information Last Updated:Friday, 18 July 2025 16:06
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Additional information on 8-Chloroadenosine 3',5'-Cyclic Monophosphate

8-Chloroadenosine 3',5'-Cyclic Monophosphate: A Comprehensive Overview

8-Chloroadenosine 3',5'-Cyclic Monophosphate, also known by its CAS number 41941-56-4, is a bioactive compound that has garnered significant attention in the fields of pharmacology and molecular biology. This compound is a derivative of adenosine monophosphate (AMP), with a chlorine substituent at the 8-position of the purine ring. Its unique structure endows it with distinct pharmacological properties, making it a valuable tool in research and potential therapeutic applications.

The synthesis of 8-Chloroadenosine 3',5'-Cyclic Monophosphate involves several steps, including the modification of adenosine to incorporate the chlorine atom at the 8-position. This substitution is crucial as it alters the compound's physicochemical properties, enhancing its stability and bioavailability. Recent studies have explored novel synthetic methodologies to improve the yield and purity of this compound, ensuring its reliability for experimental use.

One of the most notable applications of 8-Chloroadenosine 3',5'-Cyclic Monophosphate is in the study of cellular signaling pathways. This compound acts as an analog of cyclic AMP (cAMP), a key second messenger molecule involved in various cellular processes, including gene expression, metabolism, and cell proliferation. By mimicking cAMP, 8-Chloroadenosine 3',5'-Cyclic Monophosphate can modulate protein kinase A (PKA) activity, providing researchers with a powerful tool to investigate signaling cascades in vitro and in vivo.

Recent advancements in research have highlighted the potential therapeutic benefits of 8-Chloroadenosine 3',5'-Cyclic Monophosphate. For instance, studies have demonstrated its ability to inhibit certain enzymes associated with inflammatory responses, suggesting its potential use in anti-inflammatory therapies. Additionally, preclinical trials have shown promising results in models of neurodegenerative diseases, where this compound exhibits neuroprotective effects by modulating cAMP-dependent pathways.

The pharmacokinetics and toxicity profile of 8-Chloroadenosine 3',5'-Cyclic Monophosphate have also been extensively studied. Research indicates that this compound has a favorable safety profile, with minimal adverse effects observed at therapeutic concentrations. However, further studies are required to fully understand its long-term effects and mechanisms of action in complex biological systems.

In conclusion, 8-Chloroadenosine 3',5'-Cyclic Monophosphate, CAS No. 41941-56-4, represents a significant advancement in the field of bioactive compounds. Its unique properties and versatile applications make it an invaluable tool for researchers and clinicians alike. As ongoing studies continue to uncover new insights into its mechanisms and therapeutic potential, this compound is poised to play a pivotal role in the development of innovative treatments for various diseases.

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Amadis Chemical Company Limited
(CAS:41941-56-4)8-Chloroadenosine 3',5'-Cyclic Monophosphate
A1242868
Purity:99%/99%
Quantity:1mg/5mg
Price ($):758/1895
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NewCan Biotech Limited
(CAS:41941-56-4)8-Chloroadenosine-cyclic-3',5'-monophosphatedihydrate
NC12618
Purity:97%
Quantity:10g
Price ($):Inquiry
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