A9501

Adenosine 3′,5′-cyclic monophosphate

≥98.5% (HPLC), powder

• Synonym(s): 3′,5′-Cyclic AMP, Adenosine 3′,5′-cyclophosphate, cAMP
• Empirical Formula (Hill Notation): C₁₀H₁₂N₅O₆P
• CAS Number: 60-92-4
• Molecular Weight: 329.21
• Beilstein: 52645
• EC Number: 200-492-9
• MDL number: MFCD00005845
• eCl@ss: 32160414
• PubChem Substance ID: 24278245
• NACRES: NA.77

Properties

• Quality Level: 200
• Assay: ≥98.5% (HPLC)
• form: powder
• color: white
• mp: 260 °C (dec.) (lit.)
• 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
• SMILES string: Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O
• 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
• Gene Information: human ... OPRK1(4986)

Description

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.

Safety Information

• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves