Name: Cyclic AMP
SKU: 60-92-4

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Basic Information

Molecular Structure:
CAS No.:	60-92-4
Name:	Cyclic AMP

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

Synthetic route

: C22H38N6O6P(1+)

: 74-88-4
methyl iodide

A: 58937-08-9, 62742-70-5, 62989-52-0
O3',O5'-methoxyphosphoryl-adenosine

B: 50884-82-7
O3',O5'-hydroxyphosphoryl-1-methyl-6,N6-didehydro-1,6-dihydro-adenosine

C: 60-92-4
cAMP

Conditions

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

...Expand

: 100-39-0
benzyl bromide

: C22H38N6O6P(1+)

A: 55053-32-2
(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: 137157-07-4
(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: 60-92-4
cAMP

D: 62742-71-6
cAMP benzyl ester

Conditions

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.

...Expand

: 34051-17-7
C10H12Cl2N5O5P

: 60-92-4
cAMP

Conditions

Conditions	Yield
With potassium hydroxide In water; acetonitrile at 0℃; Yield given;

: 73706-11-3
2-carboxy-1,N6-etheno adenosine 3',5'-cyclic phosphate

: 60-92-4
cAMP

Conditions

Conditions	Yield
In dimethyl sulfoxide Heating; role of the 1,N6-etheno bridge in decarboxylation (without that decarboxylation did not take place at all);

: 143546-26-3
desyl adenosine cyclic 3',5'-phosphate

A: 1839-72-1
2-phenylbenzofuran

B: 60-92-4
cAMP

Conditions

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;

: <4-(7-Methoxycoumarinyl)>methyl adenosine cyclic 3',5'-monophosphate

A: 72433-26-2
6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran

B: 60-92-4
cAMP

Conditions

Conditions	Yield
With water In 1,4-dioxane Irradiation;

: equatorial-(7-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

A: 72433-26-2
6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran

B: 60-92-4
cAMP

Conditions

Conditions	Yield
With HEPES buffer In methanol; water Quantum yield; photolytic cleavage; UV-irradiation;
In methanol; water pH=7.2; Quantum yield; UV-irradiation;

: axial-(7-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

A: 72433-26-2
6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran

B: 60-92-4
cAMP

Conditions

Conditions	Yield
With HEPES buffer In methanol; water Quantum yield; photolytic cleavage; UV-irradiation;
In methanol; water pH=7.2; Quantum yield; UV-irradiation;

: 58-64-0
adenosine 5'-diphosphate

adenylate-cyclase: adenylate-cyclase

: 60-92-4
cAMP

AMP: AMP

: 60-92-4
cAMP

Conditions

Conditions	Yield
With pyridine; tributyl-amine; dicyclohexyl-carbodiimide

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Chemistry

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

Uses

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.

Production

Cyclic AMP is synthesised from ATP by adenylyl cyclase located on the inner side of the plasma membrane.

Toxicity Data With Reference

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.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: Corrosive C, Irritant 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 PO_x and NO_x.

Specification

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.

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Chemistry

Uses

Production

Toxicity Data With Reference

Consensus Reports

Safety Profile

Specification