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CAS No.: | 60-92-4 |
---|---|
Name: | Cyclic AMP |
Article Data: | 37 |
Molecular Structure: | |
Formula: | C10H12N5O6P |
Molecular Weight: | 329.209 |
Synonyms: | 3',5'-AMP;AMPc;Adenosine 3',5'-cyclophosphate;Adenosine 3',5'-monophosphate;Adenosine 3',5'-phosphate;Adenosine cyclic 3',5'-monophosphate;Adenosine cyclic monophosphate;Cyclic 3',5'-AMP;Cyclic3',5'-adenylic acid;Cyclic adenosine 3',5'-monophosphate;Cyclicadenosine 3',5'-phosphate;NSC 143670;NSC 94017;cAMP; |
EINECS: | 200-492-9 |
Density: | 2.47 g/cm3 |
Melting Point: | 260 °C (dec.)(lit.) |
Boiling Point: | 701.5 °C at 760 mmHg |
Flash Point: | 378 °C |
Solubility: | 50 mg/mL in water |
Appearance: | white crystalline powder |
Hazard Symbols: | C, Xi |
Risk Codes: | 34-36/37/38 |
Safety: | 22-24/25-45-36/37/39-26-36 |
PSA: | 164.65000 |
LogP: | -0.23620 |
methyl iodide
A
O3',O5'-methoxyphosphoryl-adenosine
B
O3',O5'-hydroxyphosphoryl-1-methyl-6,N6-didehydro-1,6-dihydro-adenosine
C
cAMP
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl acetamide at 80℃; for 0.0833333h; Yields of byproduct given; | A 68.5% B n/a C n/a |
benzyl bromide
A
(4aR,6R,7R,7aS)-6-(1-Benzyl-6-imino-1,6-dihydro-purin-9-yl)-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol
B
(4aR,6R,7R,7aS)-6-(1-Benzyl-6-imino-1,6-dihydro-purin-9-yl)-2-benzyloxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
C
cAMP
D
cAMP benzyl ester
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl acetamide at 80℃; for 0.25h; | A n/a B 0.7% C n/a D 34% |
With sodium carbonate In N,N-dimethyl acetamide at 80℃; for 0.25h; Product distribution; other alkyl halide; var. inorganic carbonates; | A 2 % Chromat. B 5 % Chromat. C 17 % Chromat. D 74 % Chromat. |
C10H12Cl2N5O5P
cAMP
Conditions | Yield |
---|---|
With potassium hydroxide In water; acetonitrile at 0℃; Yield given; |
2-carboxy-1,N6-etheno adenosine 3',5'-cyclic phosphate
cAMP
Conditions | Yield |
---|---|
In dimethyl sulfoxide Heating; role of the 1,N6-etheno bridge in decarboxylation (without that decarboxylation did not take place at all); |
Conditions | Yield |
---|---|
In 1,4-dioxane; water Quantum yield; Rate constant; Mechanism; Irradiation; var. solvents, var. pH; | |
With Tris buffer In water-d2 at 40℃; Quantum yield; Irradiation; |
A
6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran
B
cAMP
Conditions | Yield |
---|---|
With water In 1,4-dioxane Irradiation; |
A
6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran
B
cAMP
Conditions | Yield |
---|---|
With HEPES buffer In methanol; water Quantum yield; photolytic cleavage; UV-irradiation; | |
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
A
6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran
B
cAMP
Conditions | Yield |
---|---|
With HEPES buffer In methanol; water Quantum yield; photolytic cleavage; UV-irradiation; | |
In methanol; water pH=7.2; Quantum yield; UV-irradiation; |
cAMP
Conditions | Yield |
---|---|
With pyridine; tributyl-amine; dicyclohexyl-carbodiimide |
Molecule structure of Cyclic AMP (CAS NO.60-92-4):
IUPAC Name: (1S,6R,8R,9R)-8-(6-Aminopurin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3λ5-phosphabicyclo[4.3.0]nonan-9-ol
Molecular Formula: C10H12N5O6P
Molecular Weight: 329.24 g/mol
EINECS: 200-492-9
Density: 2.47 g/cm3
Melting Point: 260 °C
Boiling Point: 701.5 °C at 760 mmHg
Flash Point: 378 °C
Water Solubility: 50 mg/mL
Index of Refraction: 2.011
Molar Refractivity: 67.04 cm3
Molar Volume: 133 cm3
Surface Tension: 153.8 dyne/cm
XLogP3-AA: -2.6
H-Bond Donor: 3
H-Bond Acceptor: 10
Rotatable Bond Count: 1
Tautomer Count: 3
Exact Mass: 329.05252
MonoIsotopic Mass: 329.05252
Topological Polar Surface Area: 155
Heavy Atom Count: 22
Canonical SMILES: C1C2C(C(C(O2)N3C=NC4=C3N=CN=C4N)O)OP(=O)(O1)O
Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=CN=C4N)O)OP(=O)(O1)O
InChI: 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
Product Categories: Pharmaceutical Intermediates; Nucleotides and Nucleic Acids; Nucleic acids
Cyclic AMP (CAS NO.60-92-4) is used for intracellular signal transduction, such as transferring the effects of hormones like adrenaline and glucagon, which cannot pass through the cell membrane. Cyclic AMP also regulates the passage of Ca2+ through ion channels.
Cyclic AMP is synthesised from ATP by adenylyl cyclase located on the inner side of the plasma membrane.
1. | oms-hmn:oth 100 µmol/L | JIDEAE Journal of Investigative Dermatology. 65 (1975),52. | ||
2. | oms-mus:fbr 1 mmol/L | IJCNAW International Journal of Cancer. 13 (1974),404. | ||
3. | dns-ham:oth 130 mmol/L | CNREA8 Cancer Research. 42 (1982),3669. |
Reported in EPA TSCA Inventory.
Hazard Codes: C, Xi
Risk Statements: 34-36/37/38
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-45-36/37/39-26-36
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: AU7357600
F: 10-21
Human mutation data reported. When heated to decomposition it emits toxic fumes of POx and NOx.
Cyclic AMP (CAS NO.60-92-4) is also named as 3',5'-AMP ; 4-26-00-03618 (Beilstein Handbook Reference) ; Adenosine 3',5'-cyclic monophosphate ; Adenosine 3',5'-cyclophosphate ; Adenosine 3',5'-monophosphate ; Adenosine 3',5'-phosphate ; Adenosine cyclic 3',5'-phosphate ; Adenosine cyclic monophosphate ; cAMP ; cyclic 3',5'-AMP ; cyclic 3',5'-Adenylic acid ; cyclic Adenosine 3',5'-monophosphate ; cyclic Adenosine 3',5'-phosphate . Cyclic AMP (CAS NO.60-92-4) is white crystalline powder. It is slightly soluble in water, almost insoluble in ethanol or ether.