cAMP
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cAMP
structure -
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CAS No:
60-92-4
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Formula:
C10H12N5O6P
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Chemical Name:
cAMP
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Synonyms:
Adenosine,cyclic 3′,5′-(hydrogen phosphate);Adenosine 3′,5′-cyclic phosphate;4H-Furo[3,2-d]-1,3,2-dioxaphosphorin,adenosine deriv.;3′,5′-AMP;Adenosine cyclic 3′,5′-monophosphate;Adenosine 3′,5′-cyclophosphate;Adenosine 3′,5′-monophosphate;Adenosine 3′,5′-phosphate;Cyclic adenosine 3′,5′-phosphate;Cyclic 3′,5′-adenylic acid;Cyclic 3′,5′-monophosphate adenosine;Cyclic-3′,5′-phosphate adenosine;Cyclic AMP;Cyclic adenosine 3′,5′-monophosphate;Cyclic 3′,5′-AMP;cAMP;Adenosine cyclic monophosphate;NSC 143670;NSC 94017;AMPc;NQZ-026;11002-78-1
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CAS No:
Description
cAMP is a mitogenic messenger and promotes the G1 to S phase transition in the cell cycle.
Solid
3',5'-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-).|Cyclic adenosine monophosphate (cAMP, cyclic AMP or 3'-5'-cyclic adenosine monophosphate) is a molecule that is important in many biological processes; it is derived from adenosine triphosphate (ATP).|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.|An adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH.
Characteristics
155
-2.96
white powder
2.5±0.1 g/cm3
219-220 °C
701.5°C at 760 mmHg
378.0±35.7 °C
2.012
H2O: 10 mg/mL pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble ., clear, colorless
2-8°C
oms-hmn:oth 100 mmol/L JIDEAE 65,52,75
Flammable; heat produces toxic nitrogen oxides and phosphorus oxide fumes
-53.7 º (c=0.7,water)
176.8 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|175.07 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|172 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]|172.6 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|176.8 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|181 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|188.6 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|188.8 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|171.8 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|172 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|171.9 Ų [M-H]-
Safety Information
NONH for all modes of transport
3
34-36/37/38
22-24/25-45-36/37/39-26-36
AU7357600
C,Xi
Warehouse ventilated, low temperature and dry
P260, P261, P264, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
H314
|Danger|H314 (25%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P261, P264, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 6 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
cAMP Use and Manufacturing
5'-AMP is used as the raw material for the preparation of 5'-AMP double salt. The feed ratio is N, N'-bicyclohexylmorphine (m): pyridine (V): 5'-AMP(m): water (V) )=1:9.62:1.19:1.7. Add N, N'-dicyclohexylmorpholine guanidine and pyridine into the reactor, heat to 80°C to dissolve, then add 5'-AMP and water, after 5'-AMP is dissolved, distill to dryness under reduced pressure at 80°C, Add a small amount of anhydrous pyridine, evaporate to dryness under reduced pressure, and repeat twice to obtain the product. 5'-AMP[N, N'-Dicyclohexylmorpholine guanidine, pyridine]→[80℃]5'-AMP double salt cAMP crude product preparation feed ratio is 5'-AMP double salt (m): anhydrous pyridine (V): Dicyclohexylcarbodiimide (V)=1:235:1.07. First mix one-half the amount of anhydrous pyridine and bicyclohexylcarbodiimide, reflux at 140-145℃, and mix the 5'-AMP double salt with the other half of the anhydrous under reflux The pyridine mixed solution was added slowly in batches, and the addition was completed within about 3 hours. After the addition, the reflux was continued for 6 hours, cooled, and the pyridine was evaporated under reduced pressure at 70°C to dryness. The residue was dissolved in a mixture of ether and water (1:1.5). The insoluble dicyclohexylurea was removed by filtration, the aqueous layer in the filtrate was separated, and then washed with ether three times, and the remaining ether was pumped out with a water pump. 5'-AMP double salt [anhydrous pyridine, dicyclohexylcarbodiimide]→[9h]cAMP crude cAMP purification The water layer is adjusted to pH 2 with hydrochloric acid, the insoluble matter is removed by filtration, and the filtrate uses 100 mesh strong base The cation exchange resin of styrene series 001×7 (732) is adsorbed, and the amount of resin is 80-100 times of 5'-AMP. Then eluted with 1.01mol/L hydrochloric acid, collected the second absorption peak (E260), neutralized with ammonium bicarbonate to neutrality, concentrated under reduced pressure at 60°C until the cAMP content was 15%-20%, filtered, and added the filtrate. After a volume of ethanol (95%), the pH is adjusted to 2 with 2mol/L hydrochloric acid, filtered, and dried to obtain the cAMP product. Crude cAMP [001×7(732) resin, hydrochloric acid, ethanol]→[pH2] cAMP product.
Natural activator of cyclized adenylate-dependent protein kinase (PKA); cAMP is an important second messenger and is associated with neurotransmitter or hormone-induced receptor activation in many systems; it has been shown that cAMP /PKA signaling pathway can inhibit cell proliferation, induce differentiation and cause apoptosis
Adenosine, cyclic 3',5'-(hydrogen phosphate): ACTIVE
Cosmetics -> Skin conditioning
Computed Properties
Molecular Weight:329.21
XLogP3:-2.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:1
Exact Mass:329.05252012
Monoisotopic Mass:329.05252012
Topological Polar Surface Area:155
Heavy Atom Count:22
Complexity:498
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It is a protein kinase activator and a derivative of nucleotides. It is an important substance with physiological activity that is widely present in the human body. It is produced by adenosine triphosphate under the catalysis of adenylate cyclase and can regulate various functional activities of cells. As the second messenger of hormones, it plays a role in regulating physiological functions and material metabolism in cells, can change the function of cell membranes, promote calcium ions in reticulum to enter muscle fibers, thereby enhancing myocardial contraction, and can promote the activity of respiratory chain oxidases, improve myocardial hypoxia, relieve symptoms of coronary heart disease and improve electrocardiograms. In addition, it plays an important role in regulating sugar, fat metabolism, nucleic acid, and protein synthesis.
Registered Holders
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Chongqing Unger Dragon Pharmaceutical Co., Ltd.
Active
China
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MEYA Haian Pharmaceutical Co., Ltd.
Active
China
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Heilongjiang Jiangshi Pharmaceutical Co., Ltd.
Active
China
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