Cyclic AMP | CAS#60-92-4 | adenine nucleotide

MedKoo Cat#: 591136 | Name: Cyclic AMP

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cyclic AMP is 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.

Chemical Structure

Cyclic AMP

CAS#60-92-4

Theoretical Analysis

MedKoo Cat#: 591136

Name: Cyclic AMP

CAS#: 60-92-4

Chemical Formula: C10H14N5O7P

Exact Mass: 347.0631

Molecular Weight: 347.22

Elemental Analysis: C, 34.59; H, 4.06; N, 20.17; O, 32.25; P, 8.92

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
250mg	USD 450.00	2 Weeks
1g	USD 850.00	2 Weeks

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Related CAS #

No Data

Synonym

Cyclic AMP; 3',5'-Cyclic AMP; 3',5'-cAMP; cAMP; NSC 94017; NSC-94017; NSC94017

IUPAC/Chemical Name

(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine 2-oxide

InChi Key

IVOMOUWHDPKRLL-KQYNXXCUSA-N

InChi Code

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

SMILES Code

NC(N=CN=C12)=C1N=CN2[C@H](O3)[C@H](O)[C@H](O4)[C@H]3COP4(O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 347.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Arumugham VB, Ulivieri C, Onnis A, Finetti F, Tonello F, Ladant D, Baldari CT. Compartmentalized Cyclic AMP Production by the Bordetella pertussis and Bacillus anthracis Adenylate Cyclase Toxins Differentially Affects the Immune Synapse in T Lymphocytes. Front Immunol. 2018 May 1;9:919. doi: 10.3389/fimmu.2018.00919. eCollection 2018. PubMed PMID: 29765373; PubMed Central PMCID: PMC5938339. 2: Freund JR, Mansfield CJ, Doghramji LJ, Adappa ND, Palmer JN, Kennedy DW, Reed DR, Jiang P, Lee RJ. Activation of airway epithelial bitter taste receptors by Pseudomonas aeruginosa quinolones modulates calcium, cyclic-AMP, and nitric oxide signaling. J Biol Chem. 2018 May 10. pii: jbc.RA117.001005. doi: 10.1074/jbc.RA117.001005. [Epub ahead of print] PubMed PMID: 29748385. 3: Jang H. Regulation of Cyclic AMP-Response Element Binding Protein Zhangfei (CREBZF) Expression by Estrogen in Mouse Uterus. Dev Reprod. 2018 Mar;22(1):95-104. doi: 10.12717/DR.2018.22.1.095. Epub 2018 Mar 31. PubMed PMID: 29707688; PubMed Central PMCID: PMC5915772. 4: Jang H. Differential Expression of Cyclic AMP-Response Element Binding Protein Zhangfei (CREBZF) in the Mouse Testis during Postnatal Development. Dev Reprod. 2018 Mar;22(1):65-72. doi: 10.12717/DR.2018.22.1.065. Epub 2018 Mar 31. PubMed PMID: 29707685; PubMed Central PMCID: PMC5915768. 5: Kjellerup L, Winther AL, Wilson D, Fuglsang AT. Cyclic AMP Pathway Activation and Extracellular Zinc Induce Rapid Intracellular Zinc Mobilization in Candida albicans. Front Microbiol. 2018 Mar 21;9:502. doi: 10.3389/fmicb.2018.00502. eCollection 2018. PubMed PMID: 29619016; PubMed Central PMCID: PMC5871664. 6: Dey S, Goswami S, Eisa A, Bhattacharjee R, Brothag C, Kline D, Vijayaraghavan S. Cyclic AMP and glycogen synthase kinase 3 form a regulatory loop in spermatozoa. J Cell Physiol. 2018 Mar 25. doi: 10.1002/jcp.26557. [Epub ahead of print] PubMed PMID: 29574946. 7: Bellomo F, Signorile A, Tamma G, Ranieri M, Emma F, De Rasmo D. Impact of atypical mitochondrial cyclic-AMP level in nephropathic cystinosis. Cell Mol Life Sci. 2018 Mar 16. doi: 10.1007/s00018-018-2800-5. [Epub ahead of print] PubMed PMID: 29549422. 8: Launer-Felty KD, Strobel SA. Enzymatic synthesis of cyclic dinucleotide analogs by a promiscuous cyclic-AMP-GMP synthetase and analysis of cyclic dinucleotide responsive riboswitches. Nucleic Acids Res. 2018 Apr 6;46(6):2765-2776. doi: 10.1093/nar/gky137. PubMed PMID: 29514227; PubMed Central PMCID: PMC5888326. 9: Hackley CR, Mazzoni EO, Blau J. cAMPr: A single-wavelength fluorescent sensor for cyclic AMP. Sci Signal. 2018 Mar 6;11(520). pii: eaah3738. doi: 10.1126/scisignal.aah3738. PubMed PMID: 29511120; PubMed Central PMCID: PMC5863242. 10: Bouabid S, Zhou FM. Cyclic AMP-producing chemogenetic activation of indirect pathway striatal projection neurons and the downstream effects on the globus pallidus and subthalamic nucleus in freely moving mice. J Neurochem. 2018 Mar 3. doi: 10.1111/jnc.14331. [Epub ahead of print] PubMed PMID: 29500819. 11: Kleppe R, Jonassen I, Døskeland SO, Selheim F. Mathematical Modelling of Nitric Oxide/Cyclic GMP/Cyclic AMP Signalling in Platelets. Int J Mol Sci. 2018 Feb 19;19(2). pii: E612. doi: 10.3390/ijms19020612. PubMed PMID: 29462984; PubMed Central PMCID: PMC5855834. 12: Chung YT, Pasquinelli V, Jurado JO, Wang X, Yi N, Barnes PF, Garcia VE, Samten B. Elevated Cyclic AMP Inhibits Mycobacterium tuberculosis-Stimulated T-cell IFN-γ Secretion Through Type I Protein Kinase A. J Infect Dis. 2018 May 5;217(11):1821-1831. doi: 10.1093/infdis/jiy079. PubMed PMID: 29438524; PubMed Central PMCID: PMC5946837. 13: Veremeyko T, Yung AWY, Dukhinova M, Kuznetsova IS, Pomytkin I, Lyundup A, Strekalova T, Barteneva NS, Ponomarev ED. Cyclic AMP Pathway Suppress Autoimmune Neuroinflammation by Inhibiting Functions of Encephalitogenic CD4 T Cells and Enhancing M2 Macrophage Polarization at the Site of Inflammation. Front Immunol. 2018 Jan 25;9:50. doi: 10.3389/fimmu.2018.00050. eCollection 2018. PubMed PMID: 29422898; PubMed Central PMCID: PMC5788911. 14: Liu B, Billington CK, Henry AP, Bhaker SK, Kheirallah AK, Swan C, Hall IP. Chloride intracellular channel 1 (CLIC1) contributes to modulation of cyclic AMP-activated whole-cell chloride currents in human bronchial epithelial cells. Physiol Rep. 2018 Jan;6(2). doi: 10.14814/phy2.13508. PubMed PMID: 29368798; PubMed Central PMCID: PMC5789713. 15: Zhao P, Wang W, Tian P. Development of cyclic AMP receptor protein-based artificial transcription factor for intensifying gene expression. Appl Microbiol Biotechnol. 2018 Feb;102(4):1673-1685. doi: 10.1007/s00253-018-8750-x. Epub 2018 Jan 16. PubMed PMID: 29335877. 16: Molina-Quiroz RC, Silva-Valenzuela C, Brewster J, Castro-Nallar E, Levy SB, Camilli A. Cyclic AMP Regulates Bacterial Persistence through Repression of the Oxidative Stress Response and SOS-Dependent DNA Repair in Uropathogenic Escherichia coli. MBio. 2018 Jan 9;9(1). pii: e02144-17. doi: 10.1128/mBio.02144-17. PubMed PMID: 29317513; PubMed Central PMCID: PMC5760743. 17: Louis T, Stahl A, Boto T, Tomchik SM. Cyclic AMP-dependent plasticity underlies rapid changes in odor coding associated with reward learning. Proc Natl Acad Sci U S A. 2018 Jan 16;115(3):E448-E457. doi: 10.1073/pnas.1709037115. Epub 2017 Dec 28. PubMed PMID: 29284750; PubMed Central PMCID: PMC5776964. 18: Selvaraj P, Shen Q, Yang F, Naqvi NI. Cpk2, a Catalytic Subunit of Cyclic AMP-PKA, Regulates Growth and Pathogenesis in Rice Blast. Front Microbiol. 2017 Nov 21;8:2289. doi: 10.3389/fmicb.2017.02289. eCollection 2017. PubMed PMID: 29209297; PubMed Central PMCID: PMC5702331. 19: Stratakis CA. Cyclic AMP-dependent protein kinase catalytic subunit A (PRKACA): the expected, the unexpected, and what might be next. J Pathol. 2018 Mar;244(3):257-259. doi: 10.1002/path.5014. Epub 2018 Jan 2. PubMed PMID: 29205368. 20: O'Grady SM. Taking intestinal anion secretion to TASK: a role for K2P channels in cyclic AMP-regulated anion secretion. J Physiol. 2018 Feb 1;596(3):359-360. doi: 10.1113/JP275567. Epub 2017 Dec 27. PubMed PMID: 29205365; PubMed Central PMCID: PMC5792558.