Product Name

  • Name

    Cyclic AMP

  • EINECS 200-492-9
  • CAS No. 60-92-4
  • Article Data37
  • CAS DataBase
  • Density 2.47 g/cm3
  • Solubility 50 mg/mL in water
  • Melting Point 260 °C (dec.)(lit.)
  • Formula C10H12N5O6P
  • Boiling Point 701.5 °C at 760 mmHg
  • Molecular Weight 329.209
  • Flash Point 378 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety 22-24/25-45-36/37/39-26-36
  • Risk Codes 34-36/37/38
  • Molecular Structure Molecular Structure of 60-92-4 (Cyclic AMP)
  • Hazard Symbols CorrosiveC, IrritantXi
  • 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;
  • PSA 164.65000
  • LogP -0.23620

Synthetic route

C22H38N6O6P(1+)

C22H38N6O6P(1+)

methyl iodide
74-88-4

methyl iodide

A

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

O3',O5'-methoxyphosphoryl-adenosine

B

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

O3',O5'-hydroxyphosphoryl-1-methyl-6,N6-didehydro-1,6-dihydro-adenosine

C

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
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
100-39-0

benzyl bromide

C22H38N6O6P(1+)

C22H38N6O6P(1+)

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
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

(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
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

cAMP
60-92-4

cAMP

D

cAMP benzyl ester
62742-71-6

cAMP benzyl ester

Conditions
ConditionsYield
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
34051-17-7

C10H12Cl2N5O5P

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
With potassium hydroxide In water; acetonitrile at 0℃; Yield given;
2-carboxy-1,N6-etheno adenosine 3',5'-cyclic phosphate
73706-11-3

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

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In dimethyl sulfoxide Heating; role of the 1,N6-etheno bridge in decarboxylation (without that decarboxylation did not take place at all);
desyl adenosine cyclic 3',5'-phosphate
143546-26-3

desyl adenosine cyclic 3',5'-phosphate

A

2-phenylbenzofuran
1839-72-1

2-phenylbenzofuran

B

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
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

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

A

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

6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran

B

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
With water In 1,4-dioxane Irradiation;
equatorial-(7-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

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

A

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

6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran

B

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
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

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

A

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

6-methoxy-1-hydroxymethyl-3-oxo-3H-benzopyran

B

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
With HEPES buffer In methanol; water Quantum yield; photolytic cleavage; UV-irradiation;
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
adenosine 5'-diphosphate
58-64-0

adenosine 5'-diphosphate

adenylate-cyclase

adenylate-cyclase

cAMP
60-92-4

cAMP

AMP

AMP

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
With pyridine; tributyl-amine; dicyclohexyl-carbodiimide
ATP( disodium-salt)

ATP( disodium-salt)

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
With barium dihydroxide
adenylate-cyclase

adenylate-cyclase

A

cAMP
60-92-4

cAMP

B

pyrophosphate

pyrophosphate

equatorial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate
339291-47-3

equatorial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In water Quantum yield; Irradiation;
axial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate
339291-37-1

axial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In water Quantum yield; Irradiation;
[7-(carboxymethoxy)coumarin-4-yl]methyl ester of cAMP
339291-49-5

[7-(carboxymethoxy)coumarin-4-yl]methyl ester of cAMP

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In water Quantum yield; Irradiation;
[7-(carboxymethoxy)coumarin-4-yl]methyl ester of cAMP
339291-40-6

[7-(carboxymethoxy)coumarin-4-yl]methyl ester of cAMP

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In water Quantum yield; Irradiation;
cyclic adenosine-3',5'-monophosphate [6,7-bis(carboxymethoxy)coumarin-4-yl]methyl ester
339291-51-9

cyclic adenosine-3',5'-monophosphate [6,7-bis(carboxymethoxy)coumarin-4-yl]methyl ester

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In water Quantum yield; Irradiation;
cyclic adenosine-3',5'-monophosphate [6,7-bis(carboxymethoxy)coumarin-4-yl]methyl ester
339291-41-7

cyclic adenosine-3',5'-monophosphate [6,7-bis(carboxymethoxy)coumarin-4-yl]methyl ester

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In water Quantum yield; Irradiation;
equatorial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate
339291-47-3

equatorial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate

A

7-(diethylamino)-4-(hydroxymethyl)-2H-chromen-2-one
54711-38-5

7-(diethylamino)-4-(hydroxymethyl)-2H-chromen-2-one

B

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
axial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate
339291-37-1

axial-[7-(diethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate

A

7-(diethylamino)-4-(hydroxymethyl)-2H-chromen-2-one
54711-38-5

7-(diethylamino)-4-(hydroxymethyl)-2H-chromen-2-one

B

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
equatorial-(coumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
402755-29-7

equatorial-(coumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

A

4-(hydroxymethyl)coumarin
35893-97-1

4-(hydroxymethyl)coumarin

B

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
axial-(coumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
402755-28-6

axial-(coumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

A

4-(hydroxymethyl)coumarin
35893-97-1

4-(hydroxymethyl)coumarin

B

cAMP
60-92-4

cAMP

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
equatorial-(6-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
402755-32-2

equatorial-(6-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

A

cAMP
60-92-4

cAMP

B

4-(hydroxymethyl)-6-methoxycoumarin

4-(hydroxymethyl)-6-methoxycoumarin

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
axial-(6-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
402755-30-0

axial-(6-methoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

A

cAMP
60-92-4

cAMP

B

4-(hydroxymethyl)-6-methoxycoumarin

4-(hydroxymethyl)-6-methoxycoumarin

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
equatorial-[7-(dimethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate

equatorial-[7-(dimethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate

A

cAMP
60-92-4

cAMP

B

7-(dimethylamino)-4-(hydroxymethyl)-2H-chromen-2-one
105567-75-7

7-(dimethylamino)-4-(hydroxymethyl)-2H-chromen-2-one

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
axial-[7-(dimethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate

axial-[7-(dimethylamino)coumarin-4-yl]methyl adenosine cyclic 3',5'-monophosphate

A

cAMP
60-92-4

cAMP

B

7-(dimethylamino)-4-(hydroxymethyl)-2H-chromen-2-one
105567-75-7

7-(dimethylamino)-4-(hydroxymethyl)-2H-chromen-2-one

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
equatorial-(6,7-dimethoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

equatorial-(6,7-dimethoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

A

cAMP
60-92-4

cAMP

B

6,7-dimethoxy-4-(hydroxymethyl)coumarin
402755-39-9

6,7-dimethoxy-4-(hydroxymethyl)coumarin

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
axial-(6,7-dimethoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate
402755-34-4

axial-(6,7-dimethoxycoumarin-4-yl)methyl adenosine cyclic 3',5'-monophosphate

A

cAMP
60-92-4

cAMP

B

6,7-dimethoxy-4-(hydroxymethyl)coumarin
402755-39-9

6,7-dimethoxy-4-(hydroxymethyl)coumarin

Conditions
ConditionsYield
In methanol; water pH=7.2; Quantum yield; UV-irradiation;
Diadenosine triphosphate
5959-90-0

Diadenosine triphosphate

A

cAMP
60-92-4

cAMP

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

C

adenosine 5'-diphosphate
58-64-0

adenosine 5'-diphosphate

D

C20H29N10O17P3

C20H29N10O17P3

Conditions
ConditionsYield
With sodium hydroxide at 90℃; Kinetics; Product distribution; Further Variations:; pH-values;
cAMP
60-92-4

cAMP

calcium dibutyryl cyclic adenosine monophosphate

calcium dibutyryl cyclic adenosine monophosphate

Conditions
ConditionsYield
With calcium chloride In ethanol; water at 20℃; for 0.166667h;96.98%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

cAMP
60-92-4

cAMP

dibutyryl cyclic AMP
362-74-3

dibutyryl cyclic AMP

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 7h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;96.09%
cAMP
60-92-4

cAMP

adenosine 3',5'-(cyclic)phosphate monosodium salt
37839-81-9

adenosine 3',5'-(cyclic)phosphate monosodium salt

Conditions
ConditionsYield
With sodium hydroxide In water at 40℃; for 0.666667h; pH=6.6 - 6.7; Temperature;96%
cAMP
60-92-4

cAMP

C10H11N5O6P(1-)*0.5Ca(2+)

C10H11N5O6P(1-)*0.5Ca(2+)

Conditions
ConditionsYield
With calcium carbonate In water at 60℃; for 0.833333h; pH=6.7 - 6.8; Reagent/catalyst; Temperature;93.8%
cAMP
60-92-4

cAMP

inosine 3′,5′-cyclic monophosphate
3545-76-4

inosine 3′,5′-cyclic monophosphate

Conditions
ConditionsYield
With phosphate buffer at 25℃; for 5h; AMP deaminase from Aspergillus sp.;93%
cAMP
60-92-4

cAMP

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2'-O-Tosyl cAMP
77056-11-2

2'-O-Tosyl cAMP

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane Ambient temperature;80%
cAMP
60-92-4

cAMP

Br-cAMP
23583-48-4

Br-cAMP

Conditions
ConditionsYield
With bromine; sodium acetate In water at 20℃; for 24h;76%
With bromine; sodium acetate In water at 20℃; for 25h;76%
With bromine; sodium acetate In water at 20℃; for 24h;
(E)-di-tert-butyl 2-(3-(7-(diethylamino)-4-(((methylsulfonyl)oxy)methyl)-2-oxo-2H-chromen-3-yl)acrylamido)succinate

(E)-di-tert-butyl 2-(3-(7-(diethylamino)-4-(((methylsulfonyl)oxy)methyl)-2-oxo-2H-chromen-3-yl)acrylamido)succinate

cAMP
60-92-4

cAMP

C39H50N7O13P

C39H50N7O13P

Conditions
ConditionsYield
Stage #1: cAMP With tributyl-amine In methanol; ethanol for 1h; Reflux;
Stage #2: (E)-di-tert-butyl 2-(3-(7-(diethylamino)-4-(((methylsulfonyl)oxy)methyl)-2-oxo-2H-chromen-3-yl)acrylamido)succinate In acetonitrile for 2.5h; Reflux;
65%
[Ru2Cl2(N,N′‑diphenylformamidinate)3]

[Ru2Cl2(N,N′‑diphenylformamidinate)3]

cAMP
60-92-4

cAMP

[Ru2Cl(N,N′‑diphenylformamidinate)3(deprotonated adenosine-3′,5′-cyclic monophosphate)]

[Ru2Cl(N,N′‑diphenylformamidinate)3(deprotonated adenosine-3′,5′-cyclic monophosphate)]

Conditions
ConditionsYield
In methanol at 20℃; for 25.5h;57%
benzyl bromide
100-39-0

benzyl bromide

cAMP
60-92-4

cAMP

cAMP benzyl ester
62742-71-6

cAMP benzyl ester

Conditions
ConditionsYield
With silver(l) oxide In dimethyl sulfoxide; acetonitrile at 65℃; for 18h;52%
4-(bromomethyl)-7-methoxycoumarin
35231-44-8

4-(bromomethyl)-7-methoxycoumarin

cAMP
60-92-4

cAMP

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

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

Conditions
ConditionsYield
With silver(l) oxide In dimethyl sulfoxide; acetonitrile at 60℃; for 45h;44%
(2E)-cyclooct-2’-en-1’-yl 4-nitrophenyl carbonate

(2E)-cyclooct-2’-en-1’-yl 4-nitrophenyl carbonate

cAMP
60-92-4

cAMP

C19H24N5O8P

C19H24N5O8P

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 30℃; for 18h;38%
cAMP
60-92-4

cAMP

2-bromomethylnaphthyl bromide
939-26-4

2-bromomethylnaphthyl bromide

A

equatorial-2-Naphthylmethyl adenosine cyclic 3',5'-monophosphate

equatorial-2-Naphthylmethyl adenosine cyclic 3',5'-monophosphate

B

axial-2-Naphthylmethyl adenosine cyclic 3',5'-monophosphate

axial-2-Naphthylmethyl adenosine cyclic 3',5'-monophosphate

Conditions
ConditionsYield
With silver(l) oxide In dimethyl sulfoxide; acetonitrile at 60℃; for 45h;A 31%
B 27%
2-(bromomethyl)anthraquinone
7598-10-9

2-(bromomethyl)anthraquinone

cAMP
60-92-4

cAMP

(2-Anthraquinonyl)methyl adenosine cyclic 3',5'-monophosphate

(2-Anthraquinonyl)methyl adenosine cyclic 3',5'-monophosphate

Conditions
ConditionsYield
With silver(l) oxide In dimethyl sulfoxide; acetonitrile at 60℃; for 45h;14%
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

cAMP
60-92-4

cAMP

7H-purin-6-ylamine
73-24-5

7H-purin-6-ylamine

Conditions
ConditionsYield
at 98℃; zeitlicher Verlauf.Hydrolysis;
at 100℃; zeitlicher Verlauf.Hydrolysis;
cAMP
60-92-4

cAMP

phosphoric acid inosine-3',5'-diyl ester
3545-76-4, 54621-38-4

phosphoric acid inosine-3',5'-diyl ester

Conditions
ConditionsYield
With potassium nitrite; water wss.Loesung vom pH 3;
cAMP
60-92-4

cAMP

A

adenosine monophosphate
84-21-9

adenosine monophosphate

B

5'-adenosine monophosphate
61-19-8

5'-adenosine monophosphate

Conditions
ConditionsYield
With cerium(III) chloride; water at 30℃; Rate constant; Mechanism; pH 8.0; velocity const. - var. pH's dependence;
With buffer pH 7; tris(3-aminopropyl)amine cobalt(III) hydroxo aqua at 25℃; relative rates of hydrolysis to the monoesters 3'-AMP and 5'-AMP; var. cobalt(III)-complexes;
With hydrogenchloride at 90.1℃; Rate constant;
furfural
98-01-1

furfural

cAMP
60-92-4

cAMP

(4aR,6R,7R,7aS)-6-(6-{[1-Furan-2-yl-meth-(Z)-ylidene]-amino}-purin-9-yl)-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

(4aR,6R,7R,7aS)-6-(6-{[1-Furan-2-yl-meth-(Z)-ylidene]-amino}-purin-9-yl)-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Conditions
ConditionsYield
With tributyl-amine In acetic acid at 50℃; for 0.5h;
Iodoethanol
624-76-0

Iodoethanol

cAMP
60-92-4

cAMP

6-Amino-9-((4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1-(2-hydroxy-ethyl)-9H-purin-1-ium

6-Amino-9-((4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1-(2-hydroxy-ethyl)-9H-purin-1-ium

Conditions
ConditionsYield
With sodium hydroxide; silver nitrate 1.) water; 2.) DMF, rt, 3 days; Yield given. Multistep reaction;
butanoic acid anhydride
106-31-0

butanoic acid anhydride

cAMP
60-92-4

cAMP

sodium bucladesine

sodium bucladesine

Conditions
ConditionsYield
With barium(II) iodide; sodium perchlorate; triethylamine 1.) pyridine, heating 3-4 min, then Rt, 6 d; 2.) water, methanol, ether; 3.) methanol, acetone; Multistep reaction;
nonan-1-al
124-19-6

nonan-1-al

cAMP
60-92-4

cAMP

(4aR,6R,7R,7aS)-6-[6-Non-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

(4aR,6R,7R,7aS)-6-[6-Non-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Conditions
ConditionsYield
With tributyl-amine In acetic acid at 50℃; for 0.5h;
cAMP
60-92-4

cAMP

(4aR,6R,7R,7aS)-6-[1-((E)-But-2-enyl)-6-imino-1,6-dihydro-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

(4aR,6R,7R,7aS)-6-[1-((E)-But-2-enyl)-6-imino-1,6-dihydro-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Conditions
ConditionsYield
With 2,6-dimethylpyridine; 1,5-Diazabicyclo[5.4.0]undec-5-ene In N,N-dimethyl-formamide at 60℃; for 5h;146 g
caprinaldehyde
112-31-2

caprinaldehyde

cAMP
60-92-4

cAMP

(4aR,6R,7R,7aS)-6-[6-Dec-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

(4aR,6R,7R,7aS)-6-[6-Dec-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Conditions
ConditionsYield
With tributyl-amine In acetic acid at 50℃; for 0.5h;
heptanal
111-71-7

heptanal

cAMP
60-92-4

cAMP

(4aR,6R,7R,7aS)-6-[6-Hept-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

(4aR,6R,7R,7aS)-6-[6-Hept-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Conditions
ConditionsYield
With tributyl-amine In acetic acid at 50℃; for 0.5h;
pentanal
110-62-3

pentanal

cAMP
60-92-4

cAMP

(4aR,6R,7R,7aS)-2-Oxo-6-[6-pent-(Z)-ylideneamino-purin-9-yl]-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

(4aR,6R,7R,7aS)-2-Oxo-6-[6-pent-(Z)-ylideneamino-purin-9-yl]-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Conditions
ConditionsYield
With tributyl-amine In acetic acid at 50℃; for 0.5h;
Octanal
124-13-0

Octanal

cAMP
60-92-4

cAMP

(4aR,6R,7R,7aS)-6-[6-Oct-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

(4aR,6R,7R,7aS)-6-[6-Oct-(Z)-ylideneamino-purin-9-yl]-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Conditions
ConditionsYield
With tributyl-amine In acetic acid at 50℃; for 0.5h;
myristylaldehyde
124-25-4

myristylaldehyde

cAMP
60-92-4

cAMP

(4aR,6R,7R,7aS)-2-Oxo-6-[6-tetradec-(Z)-ylideneamino-purin-9-yl]-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

(4aR,6R,7R,7aS)-2-Oxo-6-[6-tetradec-(Z)-ylideneamino-purin-9-yl]-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinine-2,7-diol

Conditions
ConditionsYield
With tributyl-amine In chloroform; acetic acid at 50℃; for 0.5h;

Cyclic AMP Chemical Properties

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 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. 

Cyclic AMP Production

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

Cyclic AMP 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.

Cyclic AMP Consensus Reports

Reported in EPA TSCA Inventory.

Cyclic AMP Safety Profile

Hazard Codes: CorrosiveC, IrritantXi
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 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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