Introduction：Basic information about Cyclic AMP CAS 60-92-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Cyclic AMP Basic information
| Product Name: | Cyclic AMP |
| Synonyms: | adenosine 3',5'-phosphate monohydrate;CAMP;CAMP, ADENOSINE-3',5'-CYCLIC MONOPHOSPHATE;CYCLIC AMP;CYCLIC AMP-3',5';5’-cyclicmonophosphate;6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol 2-oxide;Acrasin |
| CAS: | 60-92-4 |
| MF: | C10H12N5O6P |
| MW: | 329.21 |
| EINECS: | 200-492-9 |
| Product Categories: | Pharmaceutical Intermediates;Nucleotides and Nucleic Acids;Nucleic acids;Nucleoside Mono;60-92-4 |
| Mol File: | 60-92-4.mol |
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Cyclic AMP Chemical Properties
| Melting point | 260 °C (dec.)(lit.) |
| alpha | -53.7 º (c=0.7,water) |
| Boiling point | 56.12°C |
| density | 2.47±0.1 g/cm3(Predicted) |
| storage temp. | -20°C |
| solubility | H2O: 10 mg/mL pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× |
| pka | 1.00±0.60(Predicted) |
| form | powder |
| color | white |
| biological source | mouse |
| Water Solubility | 50 mg/mL |
| Merck | 14,2708 |
| BRN | 52645 |
| Stability: | Hygroscopic |
| Cosmetics Ingredients Functions | SKIN CONDITIONING |
| 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 |
| InChIKey | IVOMOUWHDPKRLL-KQYNXXCUSA-N |
| SMILES | Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O |
| NIST Chemistry Reference | Adenosine 3',5'-cyclic monophosphate(60-92-4) |
| EPA Substance Registry System | Adenosine, cyclic 3',5'-(hydrogen phosphate) (60-92-4) |
Safety Information
| Hazard Codes | C,Xi |
| Risk Statements | 34-36/37/38 |
| Safety Statements | 22-24/25-45-36/37/39-26-36 |
| WGK Germany | 3 |
| RTECS | AU7357600 |
| F | 10-21 |
| TSCA | TSCA listed |
| HS Code | 29349990 |
| Storage Class | 11 - Combustible Solids |
| Toxicity | oms-hmn:oth 100 mmol/L JIDEAE 65,52,75 |
Cyclic AMP Usage And Synthesis
| Chemical Properties | White crystalline or Pale yellow powder; odorless. Slightly soluble in water, almost insoluble in ethanol or ether. |
| Uses | cAMP is used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway. Restoration of several morphological characteristics of normal fibroblasts in sarcoma cells when treated with adenosine-3': 5'-cyclic monophosphate. In the presence of adenosine 3':5'-cyclic monophosphate, protein kinase I dissociated into two subunits: a subunit binding adenosine 3':5'-cyclic monophosphate, and a catalytic subunit. Stimulation of calcium uptake in platelet membrane vesicles by adenosine 3',5'-cyclic monophosphate. |
| Definition | ChEBI: Cyclic AMP is a 3',5'-cyclic purine nucleotide having having adenine as the nucleobase. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an adenyl ribonucleotide and a 3',5'-cyclic purine nucleotide. It is a conjugate acid of a 3',5'-cyclic AMP(1-). |
| Application | The chief role of cyclic AMP in several tissues seems to be to facilitate or promote the mobilization of glucose and fatty acid reserves. In the liver, glucagon and the catecholamines cause an increase in the intracellular level of cyclic AMPby stimulating adenyl cyclase. This increase in the level of .cyclic AMP leads to a net increase in hepatic glucose production by at least three mechanisms: stimulation of phosphorylase activation, suppression of glycogen synthetase activity, and stimulation of gluconeogenesis. The catecholamines also stimulate adenyl cyclase in muscle and adipose tissue. Among the principal effects of cyclic AMP in these tissues are glycogenolysis in muscle and lipolysis in adipose tissue. |
| General Description | Cyclic AMP is a second messenger molecule comprised of an adenine ribonucleotide bearing a phosphate group bound to the oxygen molecules at the 3' and 5' positions of the sugar moiety. Cyclic AMP, which is synthesized from ATP by the intracellular enzyme adenylate cyclase, modulates the activity of several hormone-dependent signal transduction pathways. |
| Biochem/physiol Actions | Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis. |
| Safety Profile | Human mutation data reported.When heated to decomposition it emits toxic fumes ofPOx and NOx. |
| Synthesis | Cyclic AMP is synthesized from ATP by adenylate cyclase located on the inner side of the plasma membrane and anchored at various locations in the interior of the cell.[1] Adenylate cyclase is activated by a range of signaling molecules through the activation of adenylate cyclase stimulatory G (Gs)-protein-coupled receptors. Adenylate cyclase is inhibited by agonists of adenylate cyclase inhibitory G (Gi)-protein-coupled receptors. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline.
cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase. |
Cyclic AMP Preparation Products And Raw materials
| Raw materials | Ammonium bicarbonate-->Dicyclohexylcarbodiimide-->Moroxydine-->Dicyclohexylcarbodide or CDCC |
| Preparation Products | 6-Thioguanine-->INOSINE-3',5'-CYCLIC PHOSPHATE |
