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Key Documents

A9376

Sigma-Aldrich

Adenosine 2′:3′-cyclic monophosphate sodium salt

≥93%

Synonym(s):

2′,3′-cAMP sodium salt

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About This Item

Linear Formula:
C10H11N5O6PNa
CAS Number:
Molecular Weight:
351.19
EC Number:
MDL number:
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

Assay

≥93%

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@H]4OP([O-])(=O)O[C@@H]34

InChI

1S/C10H12N5O6P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(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

InChI key

VSDSIACSNXHGOV-MCDZGGTQSA-M

Related Categories

Application

Adenosine 2′:3′-cyclic monophosphate sodium salt has been used in lysis buffer for affinity purification and also in microscale thermophoresis measurements. It has also been used in electrophysiological studies of Tenebrio tubules.

Biochem/physiol Actions

Adenosine 2′,3′-cyclic monophosphate (2′,3′-cAMP) is believed to serve as an extracellular source of adenosine. The release of extracellular 2′,3′-cAMP occurs in response to injury. 2′,3′-cAMP may be used to study the distribution and specificity of its degrading enzymes in the context of unique biological activities. 2′,3′-cAMP may also be used to study apoptosis induced at the level of mitochondrial permeability transition pores. 2′,3′-cAMP is converted into 2′-AMP and 3′-AMP which inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors.

Caution

Caution: Do not confuse with the common adenosine 2′(3′)-monophosphate (mixed isomers).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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J Azuma et al.
Journal of molecular and cellular cardiology, 15(1), 43-52 (1983-01-01)
Trapidil, a coronary vasodilator and positive inotropic agent, was tested for its ability to affect the normal "fast" action potentials and the "slow" action potentials and contractions of isolated perfused chick hearts, and to affect the tissue cyclic AMP level.
E I Budowsky et al.
European journal of biochemistry, 220(1), 97-104 (1994-02-15)
The action of the guanylyl-preferring RNase from Bacillus intermedius (binase) on a mixture of oligoadenylates with randomly distributed 2'-5' and 3'-5' internucleotide bonds [(A2'/3'p)n] under conditions sufficient for complete hydrolysis of poly(A) results in a mixture containing a single circular
The effects of endogenous diuretic and antidiuretic peptides and their second messengers in the Malpighian tubules of Tenebrio molitor: an electrophysiological study.
Wiehart UIM, et al.
Journal of Insect Physiology, 49(10), 955-965 (2003)
E Witters et al.
Journal of chromatography. B, Biomedical sciences and applications, 694(1), 55-63 (1997-06-20)
An LC-MS method has been developed combining ion-pair chromatography with an electrospray interface linking microbore and capillary HPLC to mass spectrometry. Separation of cyclic nucleotides on C18 reversed-phase columns, using tetrabutylammonium bromide as an ion pairing agent was evaluated with
Sandrine Evellin et al.
Methods in molecular biology (Clifton, N.J.), 284, 259-270 (2004-06-03)
cAMP is a ubiquitous second messenger that controls numerous cellular events including movement, growth, metabolism, contraction, and synaptic plasticity. With the emerging concept of compartmentalization of cAMP-dependent signaling, a detailed study of the spatio-temporal intracellular dynamics of cAMP is required.

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