Cyclic AMP

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;60-92-4
Mol File:60-92-4.mol
Cyclic AMP Structure
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×
pka1.00±0.60(Predicted)
form powder
color white
Water Solubility 50 mg/mL
Merck 14,2708
BRN 52645
Stability:Hygroscopic
NIST Chemistry ReferenceAdenosine 3',5'-cyclic monophosphate(60-92-4)
EPA Substance Registry SystemAdenosine, 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
10-21
TSCA Yes
HS Code 29349990
Toxicityoms-hmn:oth 100 mmol/L JIDEAE 65,52,75
MSDS Information
ProviderLanguage
3'-5' Cyclic adenosine monophosphate English
SigmaAldrich English
ACROS English
Cyclic AMP Usage And Synthesis
Chemical PropertiesWhite crystalline or Pale yellow powder; odorless. Slightly soluble in water, almost insoluble in ethanol or ether.
UsescAMP 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.
DefinitionChEBI: 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-).
General DescriptionCyclic 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 ActionsNaturally-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 ProfileHuman mutation data reported.When heated to decomposition it emits toxic fumes ofPOx and NOx.
SynthesisCyclic 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 materialsAmmonium bicarbonate-->Dicyclohexylcarbodiimide-->Moroxydine-->Dicyclohexylcarbodide or CDCC
Preparation Products6-Thioguanine-->INOSINE-3',5'-CYCLIC PHOSPHATE
Adenosine 3',5'-cyclic monophosphate sodium salt ADENOSINE N1-OXIDE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT 2'-O-MONOSUCCINYLADENOSINE 3':5'-CYCLIC MONOPHOSPHATE 8-(4-CHLOROPHENYLTHIO)-ADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT phosphate ester starch 8-AZIDOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE Vidarabine monophosphate 8-BROMOADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT CYCLIC AMP TRIS SALT Dibutyryl adenosine cyclophosphate calcium N6,2'-O-DISUCCINYLADENOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT Adenosine 8-AHA-CAMP Clindamycin phosphate Bucladesine sodium ADENOSINE 3',5'-CYCLIC MONOPHOSPHATE, N6,O2'-DIOCTANOYL-, SODIUM SALT 2'-O-MB-CAMP SODIUM SALT SULPHOSUCCINIC ACID ESTER

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