A166

Sp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt hydrate

≥98% (HPLC), solid

• Synonym(s): Sp-Cyclic 3′,5′-hydrogen phosphorothioate adenosine hydrate, Sp-cAMPS triethylammonium salt
• Empirical Formula (Hill Notation): C₁₀H₁₁N₅O₅PS · C₆H₁₆N · xH₂O
• CAS Number: 93602-66-5
• Molecular Weight: 446.46 (anhydrous basis)
• MDL number: MFCD01459901
• UNSPSC Code: 41106305
• PubChem Substance ID: 24890576
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: solid
• optical activity: [α]22/D −25.43°, c = 0.99 in H₂O(lit.)
• color: white
• solubility: H₂O: soluble
• storage temp.: −20°C
• SMILES string: CCN(CC)CC.Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4CO[P@@](S)(=O)O[C@H]4[C@H]3O
• InChI: 1S/C10H12N5O5PS.C6H15N/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7;1-4-7(5-2)6-3/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13);4-6H2,1-3H3/t4-,6-,7-,10-,21+;/m1./s1
• InChI key: OXIPZMKSNMRTIV-BIQAKYJPSA-N

Description

Biochem/physiol Actions

Sp-Diastereomer of adenosine 3′,5′-cyclic monophosphorothioate is a potent, membrane-permeable activator of cAMP dependent protein kinase I and II that mimics the effects of cAMP as a second messenger in numerous systems while being resistant to cyclic nucleotide phosphodiesterases; exhibits greater specificity and affinity than forskolin and cAMP analogs such as dibutyryl-cAMP.

Safety Information

• 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