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Adenosine 3′,5′-cyclic monophosphate

SIGMA/A9501 - ≥98.5% (HPLC), powder

Synonym: 3′,5′-Cyclic AMP; Adenosine 3′,5′-cyclophosphate; cAMP

CAS Number: 60-92-4
Empirical Formula (Hill Notation): C10H12N5O6P
Molecular Weight: 329.21
EC Number: 200-492-9
MDL Number: MFCD00005845
Linear Formula: C10H12N5O6P
Product Type: Chemical

Catalog Number PKG Qty. Price Quantity
45-A9501-1G 1 g
$295.00
1/EA
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45-A9501-5G 5 g
$1120.00
1/EA
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45-A9501-25G 25 g
$2760.00
1/EA
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This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A9501-1G

 

assay ≥98.5% (HPLC)
color white
form powder
InChI 1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChI key IVOMOUWHDPKRLL-KQYNXXCUSA-N
mp 260 °C (dec.) (lit.)
Quality Level 200 
SMILES string Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O
solubility H2O: 10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.)
storage temp. −20°C
Application: Adenosine 3′,5′-cyclic monophosphate has been used:
• as cell culture medium supplement in embryonic spinal neurons
• as a component of ringer solution for perfusion studies
• to induce neuroendocrine differentiation in human lung cancer cell lines

Biochem/physiol Actions: Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis.
Features and Benefits: This compound is a featured product for ADME Tox and Cyclic Nucleotide research. Discover more featured ADME Tox  and Cyclic Nucleotide  products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm .
Packaging: 1, 5, 25 g in poly bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98.5% (HPLC)
mp 260 °C (dec.) (lit.)
Storage Temp. −20°C
UNSPSC 41106305

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