A second messenger
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Cyclic AMP

Item No. 18820

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclic 3',5'-(hydrogen phosphate) adenosine
CAS Number
60-92-4
Synonyms
  • Adenosine 3',5'-cyclic monophosphate
  • cAMP
  • Cyclic adenosine monophosphate
  • NSC 94017
  • NSC 143670
Molecular Formula
C10H12N5O6P
Formula Weight
329.2
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/mlWater: 10 mg/ml
SMILES
O[C@H]1[C@H](N2C=NC3=C2N=CN=C3N)O[C@@]4([H])[C@@]1([H])OP(OC4)(O)=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

    $59

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    1 g

    $94

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    5 g

    $292

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    Product Description

    Cyclic AMP (cAMP) is a central second messenger in cell signaling, propagating signals from receptors to downstream pathways. It is generated from ATP by several adenylate cyclase enzymes, which are modulated by G protein-coupled receptors.1 cAMP activates protein kinase A and the exchange proteins activated by cAMP (Epac1 and Epac2), which are nucleotide exchange factors for the Rap family of GTPases.2,3 cAMP is degraded to AMP by cyclic nucleotide phosphodiesterases.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dorsam, R.T., and Gutkind, J.S. G-protein-coupled receptors and cancer. Nat. Rev. Cancer 7(2), 79-94 (2007).

    2. Shabb, J.B. Physiological substrates of cAMP-dependent protein kinase. Chem. Rev. 101, 2381-2411 (2001).

    3. Breckler, M., Berthouze, M., Laurent, A.C., et al. Rap-linked cAMP signaling Epac proteins: Compartmentation, functioning and disease implications. Cell. Signal. 23(8), 1257-1266 (2011).

    4. Scott, J.D., Dessauer, C.W., and Tasken, K. Creating order from chaos: Cellular regulation by kinase anchoring. Annu. Rev. Pharmacol. Toxicol. 53, 187-210 (2013).