Cyclic AMP (Cyclic adenosine monophosphate) sodium is an analogue of adenosine triphosphate and is an intracellular signaling molecule responsible for directing the cell's response to extracellular signals. Cyclic AMP sodium is an important second messenger in many biological processes.

Physicochemical Properties

Molecular Formula	C10H11N5NAO6P
Molecular Weight	351.19
Exact Mass	351.034
CAS #	37839-81-9
Related CAS #	Cyclic AMP;60-92-4
PubChem CID	23669773
Appearance	White to off-white solid powder
Boiling Point	701.5ºC at 760 mmHg
Melting Point	219 - 220ºC
Flash Point	378ºC
LogP	0.202
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	1
Heavy Atom Count	23
Complexity	504
Defined Atom Stereocenter Count	4
SMILES	C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)[O-].[Na+]
InChi Key	BXJBFCKTIWRKMQ-MCDZGGTQSA-M
InChi Code	InChI=1S/C10H12N5O6P.Na/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);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1
Chemical Name	sodium;(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
Synonyms	Cyclic AMP sodium; 37839-81-9; cAMP-Na; 3',5'-Amp sodium salt; Cyclic 3',5'-amp sodium salt; Cyclic AMP (sodium); MFCD00069736; Cyclic 3',5'-(hydrogen phosphate)adenosine monosodium salt;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Endogenous Metabolite; Microbial Metabolite
ln Vitro	Cyclic adenosine monophosphate, or cyclic AMP, sodium controls the production of mediators. Cyclic AMP sodium increases the synthesis of the anti-inflammatory cytokine IL-10 while suppressing the expression of pro-inflammatory cytokines such as TNF-α and IL-12.
Cell Assay	cAMP was the first second messenger to be identified. Its three main effectors are PKA (which phosphorylates numerous metabolic enzymes), EPAC (a guanine-nucleotide-exchange factor), and cyclic-nucleotide-gated ion channels.[2] Cyclic adenosine monophosphate (cAMP) is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Once believed to signal exclusively through its ability to bind protein kinase A (PKA), recent research has revealed alternative cAMP-binding targets involved in PKA-independent processes. In this study we addressed the hypothesis that the guanine nucleotide exchange protein directly activated by cAMP (Epac-1) and PKA differentially regulate inflammatory mediator production in distinct phagocytic cell types. To accomplish this, we compared the release of cAMP-regulated polypeptide inflammatory mediators in both macrophages (obtained from the lung and peritoneum) and bone marrow-derived dendritic cells (DCs) stimulated with bacterial endotoxin. Using the highly selective Epac-1 and PKA activating cAMP analogs 8-pCPT-2 -O-Me-cAMP and 6-Bnz-cAMP, respectively, we found that macrophages differ from DCs in the involvement of these distinct cAMP pathways in modulating inflammatory mediator release in response to endotoxin. Whereas the regulation of cytokine and chemokine production in macrophages by cAMP was solely dependent on PKA, we found that both Epac-1 and PKA activation could regulate mediator production in DCs. This finding may be important in the pharmacologic regulation of immune responses through manipulation of cAMP signaling cascades and contributes to our understanding of the differences between these cell types. [3]
Toxicity/Toxicokinetics	23669773 mouse LD50 oral 14300 mg/kg BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX); BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY); GASTROINTESTINAL: OTHER CHANGES Journal of Toxicological Sciences., 1(2)(15), 1976 23669773 mouse LD50 intraperitoneal 395 mg/kg BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX); BEHAVIORAL: TREMOR; BEHAVIORAL: ATAXIA Journal of Toxicological Sciences., 1(2)(15), 1976 23669773 mouse LD50 intravenous 645 mg/kg BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX); BEHAVIORAL: TREMOR; BEHAVIORAL: ATAXIA Journal of Toxicological Sciences., 1(2)(15), 1976
References	[1]. Cyclic AMP signaling. J Cell Sci. 2001 Jun;114(Pt 11):1971-2. [2]. The cyclic AMP pathway. Cold Spring Harb Perspect Biol. 2012 Dec 1;4(12):a011148. [3]. Short communication: differences between macrophages and dendritic cells in the cyclic AMP-dependent regulation of lipopolysaccharide-induced cytokine and chemokine synthesis. J Interferon Cytokine Res. 2006 Nov;26(11):827-33.
Additional Infomation	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 metabolite found in or produced by Escherichia coli (strain K12, MG1655). Cyclic AMP has been reported in Ziziphus jujuba, Secale cereale, and other organisms with data available. 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. 3',5'-cyclic AMP is a metabolite found in or produced by Saccharomyces cerevisiae. 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. See also: Jujube fruit (part of).

Solubility Data

Solubility (In Vitro)

DMSO: 50 mg/mL (142.37 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.12 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.8475 mL	14.2373 mL	28.4746 mL
	5 mM	0.5695 mL	2.8475 mL	5.6949 mL
	10 mM	0.2847 mL	1.4237 mL	2.8475 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.