A2224

Sigma-Aldrich

Adenosine 3′,5′-cyclic monophosphate acetoxymethyl ester

>97% (HPLC)

Synonym(s):
cAMP AM
Empirical Formula (Hill Notation):
C13H16N5O8P
CAS Number:
Molecular Weight:
401.27
MDL number:
PubChem Substance ID:

assay

>97% (HPLC)

packaging

pkg of 1 μmol

storage temp.

−20°C

SMILES string

CC(=O)OCOP1(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O1)n3cnc4c(N)ncnc34

InChI

1S/C13H16N5O8P/c1-6(19)22-5-24-27(21)23-2-7-10(26-27)9(20)13(25-7)18-4-17-8-11(14)15-3-16-12(8)18/h3-4,7,9-10,13,20H,2,5H2,1H3,(H2,14,15,16)/t7-,9-,10-,13-,27?/m1/s1

InChI key

USKCKKDBQFHVEK-OQEAWBJFSA-N

Biochem/physiol Actions

Membrane-permeable precursor of the second messenger cyclic AMP

Certificate of Analysis

Certificate of Origin

C Schultz et al.
The Journal of biological chemistry, 268(9), 6316-6322 (1993-03-25)
Acetoxymethyl esters of alkyl or aryl phosphates can be prepared by reacting their trialkylammonium or silver salts with acetoxymethyl bromide. Because acetoxymethyl esters are rapidly cleaved intracellularly, they facilitate the delivery of organophosphates into the cytoplasm without puncturing or disruption...

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