Cyclic AMP

Base Information

• Chemical Name: Cyclic AMP
• CAS No.: 60-92-4
• Deprecated CAS: 11002-78-1
• Molecular Formula: C10H12N5O6P
• Molecular Weight: 329.209
• Hs Code.: 29349990
• European Community (EC) Number: 200-492-9
• UNII: E0399OZS9N
• DSSTox Substance ID: DTXSID8040436
• Nikkaji Number: J4.811I
• Wikipedia: Cyclic_adenosine_monophosphate
• Wikidata: Q210041
• NCI Thesaurus Code: C208
• RXCUI: 1314330
• Pharos Ligand ID: W51RSGLY9KFV
• Metabolomics Workbench ID: 37050
• ChEMBL ID: CHEMBL316966
• Mol file: 60-92-4.mol

Synonyms:3',5'-Monophosphate, Adenosine Cyclic;Adenosine Cyclic 3',5' Monophosphate;Adenosine Cyclic 3',5'-Monophosphate;Adenosine Cyclic 3,5 Monophosphate;Adenosine Cyclic Monophosphate;Adenosine Cyclic-3',5'-Monophosphate;AMP, Cyclic;Cyclic 3',5'-Monophosphate, Adenosine;Cyclic AMP;Cyclic AMP, (R)-Isomer;Cyclic AMP, Disodium Salt;Cyclic AMP, Monoammonium Salt;Cyclic AMP, Monopotassium Salt;Cyclic AMP, Monosodium Salt;Cyclic AMP, Sodium Salt;Cyclic Monophosphate, Adenosine;Cyclic-3',5'-Monophosphate, Adenosine;Monophosphate, Adenosine Cyclic

Chemical Property of Cyclic AMP

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.18E-20mmHg at 25°C
• Melting Point: 260 °C (dec.)(lit.)
• Boiling Point: 701.5 °C at 760 mmHg
• PKA: 1.00±0.60(Predicted)
• Flash Point: 378 °C
• PSA: 164.65000
• Density: 2.47 g/cm³
• LogP: -0.23620
• Storage Temp.: 2-8°C
• Solubility.: H2O: 10 mg/mL pH of aqueous solution is approx. 3.0. The so
• Water Solubility.: 50 mg/mL
• XLogP3: -2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 1
• Exact Mass: 329.05252012
• Heavy Atom Count: 22
• Complexity: 498

Purity/Quality:

99.5% ^*data from raw suppliers

Cyclic AMP ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 22-24/25-45-36/37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)O
• Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)O
• 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.

Technology Process of Cyclic AMP

There total 40 articles about Cyclic AMP which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.5%

C22H38N6O6P(1+) + methyl iodide (74-88-4) → O3',O5'-methoxyphosphoryl-adenosine (58937-08-9,62742-70-5,62989-52-0) + O3',O5'-hydroxyphosphoryl-1-methyl-6,N6-didehydro-1,6-dihydro-adenosine (50884-82-7) + cAMP (60-92-4)

Guidance literature:

With sodium carbonate; In N,N-dimethyl acetamide; at 80 ℃; for 0.0833333h; Yields of byproduct given;

DOI:10.3987/COM-91-5750

Reference yield:

Diadenosine triphosphate (5959-90-0,158700-26-6) → cAMP (60-92-4) + 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) + adenosine 5'-diphosphate (58-64-0,905904-58-7) + C20H29N10O17P3

Guidance literature:

With sodium hydroxide; at 90 ℃; Further Variations:; pH-values; Kinetics; Product distribution;

DOI:10.1039/b313200e

Reference yield:

C14H16N5O8P → cAMP (60-92-4)

Guidance literature:

With sodium hydroxide; In water; at 20 - 25 ℃; for 5h; Reagent/catalyst; Industrial scale;

upstream raw materials:

benzyl bromide

C₁₀H₁₂Cl₂N₅O₅P

2-carboxy-1,N⁶-etheno adenosine 3',5'-cyclic phosphate

desyl adenosine cyclic 3',5'-phosphate

Downstream raw materials:

adenosine monophosphate

5'-adenosine monophosphate

adenosine

N⁶-Benzyl-N⁶-ethyl cAMP

Refernces

• 1、 Hirata,Hayaishi. "Adenyl cyclase of Brevibacterium liquefaciens.". . p. 1 - 11. Retrieved 1967.
• 2、 -. "Method for synthesizing cyclic adenosine monophosphate". Page/Page column 4-8. . Retrieved 2019/01/24.
• 3、 Olson, Jeremy P.,Banghart, Matthew R.,Sabatini, Bernardo L.,Ellis-Davies, Graham C. R.. "Spectral evolution of a photochemical protecting group for orthogonal two-color uncaging with visible light". supporting information. p. 15948 - 15954. Retrieved 2013/11/06.