A2224
Adenosine 3′,5′-cyclic monophosphate acetoxymethyl ester
>97% (HPLC)
Synonym(s):
cAMP AM
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About This Item
Empirical Formula (Hill Notation):
C13H16N5O8P
CAS Number:
Molecular Weight:
401.27
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
Assay
>97% (HPLC)
form
solid
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
Storage Class Code
11 - 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
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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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