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  • B5386 - 8-Bromoadenosine 3′,5′-cyclic monophosphate

B5386 Sigma-Aldrich

8-Bromoadenosine 3′,5′-cyclic monophosphate

≥97% (HPLC)

Synonym: 8-Br-A-3:5-MP, 8-Br-cAMP, 8-Bromo-cAMP

  • CAS Number 23583-48-4

  • Empirical Formula (Hill Notation) C10H11BrN5O6P

  • Molecular Weight 408.10

  •  Beilstein/REAXYS Number 591930

  •  EC Number 245-760-6

  •  MDL number MFCD00075580

  •  PubChem Substance ID 24891835

  •  NACRES NA.77



Related Categories B, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   200
assay   ≥97% (HPLC)
form   powder
mp   254 °C (dec.) (lit.)
solubility   aqueous base: soluble, clear
storage temp.   −20°C
SMILES string   Nc1ncnc2n([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)c(Br)nc12
InChI   1S/C10H11BrN5O6P/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



8-Bromoadenosine 3′,5′-cyclic monophosphate has been used:
• to treat H295R cells as positive controls for CYP19 induction
• as a membrane permeable cAMP analog to study its effect on short-circuit current (Isc)
• to investigate its potential as an inducer of differentiation in Wharton′s jelly-derived mesenchymal stem cells (WJ-MSCs)


25, 100 mg in poly bottle

5 mg in glass bottle

Biochem/physiol Actions

8-Bromoadenosine 3′,5′-cyclic monophosphate is a cell-permeable cAMP analog having greater resistance to hydrolysis by phosphodiesterases than cAMP. 8-Bromoadenosine 3′,5′-cyclic monophosphate activates protein kinase A, inhibits growth, decreases proliferation, increases differentiation, and induces apoptosis of cultured cells.

8-bromo-adenosine 3′,5′-cyclic monophosphate (8-bromo-cAMP), added to hepatocytes during plating helps to increase the acquisition of beta-adrenoceptors.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

8-Bromoadenosine 3′,5′-cyclic monophosphate is a membrane-permeable cAMP analog.

Sensitive to light and moisture


Sensitive to light and moisture.

Safety & Documentation

Safety Information

Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

How does the storage temperature relate to shipping conditions?
The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.
Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
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The lot specific COA document can be found by entering the lot number above under the "Documents" section.
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What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
How can I solubilize 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?
This product is soluble in alkaline conditions. Sigma routinely tests solubility at 50 mg/ml in 1 N ammonium hydroxide.
How can I store solutions of 8-Bromoadenosine 3',5'-cyclic monophosphate (Product No. B5386)?
The solution should be stored at -20°C, protected from light and will be stable for up to 6 months.
What is the difference between Product No. B5386 and Product No. B7880?
Product No. B5386 is the free acid form of the material, while Product No. B7880 is the sodium salt. The sodium salt aids in the water solubility of the compund.The biological function of the compounds, once dissolved, is identical.
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