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HomeProduct name listCyclic AMP

Cyclic AMP

  • CAS NO.:60-92-4
  • Empirical Formula: C10H12N5O6P
  • Molecular Weight: 329.21
  • MDL number: MFCD00005845
  • EINECS: 200-492-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
Cyclic AMP Structural

What is Cyclic AMP?

Chemical properties

White crystalline or Pale yellow powder; odorless. Slightly soluble in water, almost insoluble in ethanol or ether.

The Uses of Cyclic AMP

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.

What are the applications of Application

Adenosine 3′,5′-cyclic monophosphate is a second messenger and key intracellular regulator

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-).

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.

Properties of Cyclic AMP

Melting point: 260 °C (dec.)(lit.)
Boiling point: 56.12°C
alpha  -53.7 º (c=0.7,water)
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× more soluble., clear, colorless
pka 1.00±0.60(Predicted)
form  powder
color  white
Water Solubility  50 mg/mL
Merck  14,2708
BRN  52645
Stability: Hygroscopic
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 for Cyclic AMP

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H314:Skin corrosion/irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P310:Immediately call a POISON CENTER or doctor/physician.
P363:Wash contaminated clothing before reuse.
P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P403+P233:Store in a well-ventilated place. Keep container tightly closed.

Computed Descriptors for Cyclic AMP

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