CAS 362-74-3

Dibutyryl cAMP

Description:

Dibutyryl cAMP (CAS 362-74-3) is a synthetic derivative of cyclic adenosine monophosphate (cAMP), a crucial second messenger in cellular signaling. It is characterized by the presence of two butyryl groups attached to the nitrogen atom of the adenine moiety, which enhances its membrane permeability compared to cAMP. This modification allows dibutyryl cAMP to effectively penetrate cell membranes and activate intracellular signaling pathways. It is commonly used in biochemical research to study the role of cAMP in various physiological processes, including cell growth, differentiation, and metabolism. The compound is typically a white to off-white powder and is soluble in water and organic solvents. Its stability under physiological conditions makes it a valuable tool in pharmacological studies. Dibutyryl cAMP can activate protein kinase A (PKA) and influence various downstream effects, making it significant in the investigation of signal transduction mechanisms. However, like all chemical substances, it should be handled with care, following appropriate safety protocols in laboratory settings.

Formula: C₁₈H₂₄N₅O₈P

InChI: InChI=1S/C18H24N5O8P/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24)/t10-,14-,15-,18-/m1/s1

InChI key: InChIKey=CJGYSWNGNKCJSB-YVLZZHOMSA-N

SMILES: O(C(CCC)=O)[C@H]1[C@@H](O[C@]2([C@]1(OP(=O)(O)OC2)[H])[H])N3C=4C(N=C3)=C(NC(CCC)=O)N=CN4

Synonyms:

• (4aR,7R,7aR)-6-[6-(butanoylamino)-9H-purin-9-yl]-2-hydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl butanoate
• 3',5'-Cyclic AMP dibutyrate
• 3′,5′-Cyclic AMP dibutyrate
• 4H-Furo[3,2-d]-1,3,2-dioxaphosphorin, adenosine deriv.
• 6-[6-(butanoylamino)-9H-purin-9-yl]-2-hydroxy-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl butanoate
• Actosin
• Adenosine, N-(1-oxobutyl)-, cyclic 3',5'-(hydrogen phosphate) 2'-butanoate
• Adenosine, N-(1-oxobutyl)-, cyclic 3′,5′-(hydrogen phosphate) 2′-butanoate
• Bucladesin
• Bucladesina
• Butyramide, N-(9-β-<span class="text-smallcaps">D</span>-ribofuranosyl-9H-purin-6-yl)-, 2′-butyrate, cyclic 3′,5′-phosphate
• Butyramide, N-(9-β-<span class="text-smallcaps">D</span>-ribofuranosyl-9H-purin-6-yl)-, cyclic 3′,5′-(hydrogen phosphate) 2′-butyrate
• Butyramide, N-(9-β-D-ribofuranosyl-9H-purin-6-yl)-, 2'-butyrate, cyclic 3',5'-phosphate
• Butyramide, N-(9-β-D-ribofuranosyl-9H-purin-6-yl)-, cyclic 3',5'-(hydrogen phosphate) 2'-butyrate
• Cyclic AMP N6,2'-O-dibutyrate
• Cyclic AMP N⁶,2′-O-dibutyrate
• Cyclic AMP dibutyrate
• Cyclic dibutyryl-AMP
• Dibutyryl 3',5'-cyclic AMP
• Dibutyryl 3',5'-cyclic adenosine monophosphate
• Dibutyryl 3′,5′-cyclic AMP
• Dibutyryl 3′,5′-cyclic adenosine monophosphate
• Dibutyryl adenosine 3',5'-cyclic monophosphate
• Dibutyryl cAMP
• Dibutyryl cyclic 3',5'-AMP
• Dibutyryl cyclic 3',5'-adenylic acid
• Dibutyryl cyclic 3′,5′-AMP
• Dibutyryl cyclic 3′,5′-adenylic acid
• Dibutyryl cyclic AMP
• Dibutyryl cyclic adenosine 3',5'-monophosphate
• Dibutyryl cyclic adenosine 3′,5′-monophosphate
• Dibutyryl cyclic adenosine monophosphate
• Dibutyryl-3',5'-AMP
• Dibutyryl-3',5'-adenosine monophosphate
• Dibutyryl-3′,5′-AMP
• Dibutyryl-3′,5′-adenosine monophosphate
• Dibutyryladenosine 3',5'-cyclic monophosphate
• Dibutyryladenosine 3',5'-cyclic phosphate
• Dibutyryladenosine 3',5'-cyclophosphate
• Dibutyryladenosine 3',5'-monophosphate
• Dibutyryladenosine 3′,5′-cyclic monophosphate
• Dibutyryladenosine 3′,5′-cyclic phosphate
• Dibutyryladenosine 3′,5′-cyclophosphate
• Dibutyryladenosine 3′,5′-monophosphate
• Dibutyryladenosine cyclic 3',5'-monophosphate
• Dibutyryladenosine cyclic 3′,5′-monophosphate
• Dibutyryladenosine cyclic monophosphate
• Dt 5621
• N-(9-beta-D-Ribofuranosyl-9H-furin-6-yl)-butyramide cyclic 3',5'-(hydrogen phosphate) 2'-butyrate
• N-6,O-2'-Dibutyryl adenosine cyclic 3':5'-monophosphate
• N-6-2-O-Dibutyryl adenosine-3',5'-monophosphate
• N6,2'-Dibutyryladenosine cyclic 3',5'-(hydrogen phosphate)
• N6,2'-O-Dibutyryl 3',5'-cyclic adenosine monophosphate
• N6,2'-O-Dibutyryl cAMP
• N6,2'-O-Dibutyryl cyclic 3',5'-AMP
• N6,2'-O-Dibutyryl cyclic 3',5'-adenosine monophosphate
• N6,2'-O-Dibutyryl cyclic AMP
• N6,2'-O-Dibutyryladenosine 3',5'-monophosphate
• N6,2'-O-Dibutyryladenosine cyclic 3',5'-monophosphate
• N6,2'-O-Dibutyryladenosine cyclic 3',5'-phosphate
• N6,O2'-Dibutyryl 3',5'-AMP
• N6,O2'-Dibutyryl adenosine 3',5'-cyclic monophosphate
• N6,O2'-Dibutyryl adenosine-3',5'-phosphate
• N6,O2'-Dibutyryl cyclic 3',5'-AMP
• N6,O2'-Dibutyryl cyclic AMP
• N6,O2'-Dibutyryl cyclic adenosine 3',5'-monophosphate
• N6,O2'-Dibutyryl cyclic adenosine 3',5'-monophosphoric acid
• N6,O2'-Dibutyryl cyclic adenosine monophosphate
• N6,O2'-Dibutyryl-3',5'-cyclic AMP
• N6,O2'-Dibutyryl-cAMP
• N6,O2'-Dibutyryladenosine 3',5'-monophosphate
• N6,O2'-Dibutyryladenosine cyclic 3',5'-phosphate
• N6,O2'-Dibutyrylcyclic adenosine 3',5'-phosphate
• N6-2'-O-Dibutyryl-3',5'-AMP
• N₆-2′-O-Dibutyryl-3′,5′-AMP
• N⁶,2′-Dibutyryladenosine cyclic 3′,5′-(hydrogen phosphate)
• N⁶,2′-O-Dibutyryl 3′,5′-cyclic adenosine monophosphate
• N⁶,2′-O-Dibutyryl cAMP
• N⁶,2′-O-Dibutyryl cyclic 3′,5′-AMP
• N⁶,2′-O-Dibutyryl cyclic 3′,5′-adenosine monophosphate
• N⁶,2′-O-Dibutyryl cyclic AMP
• N⁶,2′-O-Dibutyryladenosine 3′,5′-monophosphate
• N⁶,2′-O-Dibutyryladenosine cyclic 3′,5′-monophosphate
• N⁶,2′-O-Dibutyryladenosine cyclic 3′,5′-phosphate
• N⁶,O²′-Dibutyryl 3′,5′-AMP
• N⁶,O²′-Dibutyryl adenosine 3′,5′-cyclic monophosphate
• N⁶,O²′-Dibutyryl adenosine-3′,5′-phosphate
• N⁶,O²′-Dibutyryl cyclic 3′,5′-AMP
• N⁶,O²′-Dibutyryl cyclic adenosine monophosphate
• N⁶,O²′-Dibutyryl-3′,5′-cyclic AMP
• N⁶,O²′-Dibutyrylcyclic adenosine 3′,5′-phosphate
• N⁶,O^2′-Dibutyryl cyclic AMP
• N⁶,O^2′-Dibutyryl cyclic adenosine 3′,5′-monophosphate
• N⁶,O^2′-Dibutyryl cyclic adenosine 3′,5′-monophosphoric acid
• N⁶,O^2′-Dibutyryl-cAMP
• N⁶,O^2′-Dibutyryladenosine 3′,5′-monophosphate
• N⁶,O^2′-Dibutyryladenosine cyclic 3′,5′-phosphate
• Nsc 143108
• dbcAMP
• Butyramide, N-(9-β-D-ribofuranosyl-9H-purin-6-yl)-, cyclic 3′,5′-(hydrogen phosphate) 2′-butyrate

Bucladesine Sodium Salt

CAS: 16980-89-5, 362-74-3

Formula: C₁₈H₂₃N₅NaO₈P

Purity: >95.0%(HPLC)(qNMR)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 491.37

Ref: 3B-D4228

Calcium dibutyryladenosine cyclophosphate

CAS: 362-74-3

Formula: C₁₈H₂₃N₅O₈P·Ca

Purity: ≥ 95.0% (anhydrous basis)

Color and Shape: White, off-white, beige or yellow-orange powder

Molecular weight: 508.46

Ref: 7W-GN2961

Bucladesine

CAS: 362-74-3

Bucladesine mimics cAMP, permeates cells, and inhibits phosphodiesterase; used in research.

Formula: C₁₈H₂₄N₅O₈P

Color and Shape: Solid

Molecular weight: 469.39

Ref: TM-T20214

Dibutyryladenosine cyclic 3',5'-monophosphate

CAS: 362-74-3

Dibutyryladenosine cyclic 3',5'-monophosphate (DBACMP) is a mitochondrial function regulator that inhibits the synthesis of ATP by binding to the methyltransferase enzyme. DBACMP also has an inhibitory effect on other enzymes, such as dna binding activity and enzyme activities involved in cellular energy metabolism. DBACMP inhibits infectious diseases by altering signal pathways, which leads to the production of cytokines and chemokines that have pro-inflammatory effects and stimulate axonal growth. The drug may also bind to the atp-binding cassette transporter and inhibit mitochondrial calcium uptake. DBACMP binds to polymorphonuclear leucocytes and alters cytosolic calcium levels, which may lead to an increased production of protein genes for cell growth.

Formula: C₁₈H₂₄N₅O₈P

Purity: Min. 95%

Molecular weight: 469.39 g/mol

Ref: 3D-NR145431