Adenosine-2'-monophosphate

Modify Date: 2024-01-04 10:56:06

Adenosine-2'-monophosphate Structure
Adenosine-2'-monophosphate structure
Common Name Adenosine-2'-monophosphate
CAS Number 130-49-4 Molecular Weight 347.221
Density 2.3±0.1 g/cm3 Boiling Point 815.5±75.0 °C at 760 mmHg
Molecular Formula C10H14N5O7P Melting Point N/A
MSDS USA Flash Point 447.0±37.1 °C

 Use of Adenosine-2'-monophosphate


Adenosine-2'-monophosphate (2'-AMP) is converted by extracellular 2’,3'-CAMP. Adenosine-2'-monophosphate is further metabolized to extracellular adenosine (a mechanism called the extracellular 2’,3’-cAMP-adenosine pathway). Adenosine-2'-monophosphate inhibits LPS-induced TNF-α and CXCL10 production via A2A receptor activation[1][2].

 Names

Name adenosine 2'-phosphate
Synonym More Synonyms

 Adenosine-2'-monophosphate Biological Activity

Description Adenosine-2'-monophosphate (2'-AMP) is converted by extracellular 2’,3'-CAMP. Adenosine-2'-monophosphate is further metabolized to extracellular adenosine (a mechanism called the extracellular 2’,3’-cAMP-adenosine pathway). Adenosine-2'-monophosphate inhibits LPS-induced TNF-α and CXCL10 production via A2A receptor activation[1][2].
Related Catalog
Target

Human Endogenous Metabolite

A2A adenosine receptor

A2B adenosine receptor

In Vitro Adenosine-2'-monophosphate (2'-AMP) (0-100 µM; daily for 4 days) inhibits proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors[1]. Adenosine-2'-monophosphate (30 μM; 24 hours) inhibits LPS induced (100 ng/ml) TNF-α and CXCL10 production in primary murine microglia[1].
References

[1]. Jackson EK, Gillespie DG, Dubey RK. 2'-AMP and 3'-AMP inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. J Pharmacol Exp Ther. 2011;337(2):444‐450.

[2]. Newell EA, Exo JL, Verrier JD, et al. 2',3'-cAMP, 3'-AMP, 2'-AMP and adenosine inhibit TNF-α and CXCL10 production from activated primary murine microglia via A2A receptors. Brain Res. 2015;1594:27‐35.

 Chemical & Physical Properties

Density 2.3±0.1 g/cm3
Boiling Point 815.5±75.0 °C at 760 mmHg
Molecular Formula C10H14N5O7P
Molecular Weight 347.221
Flash Point 447.0±37.1 °C
Exact Mass 347.063080
PSA 195.88000
LogP -1.74
Vapour Pressure 0.0±3.1 mmHg at 25°C
Index of Refraction 1.905
Storage condition −20°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AU7480300
CHEMICAL NAME :
2'-Adenylic acid
CAS REGISTRY NUMBER :
130-49-4
BEILSTEIN REFERENCE NO. :
0058366
LAST UPDATED :
199612
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C10-H14-N5-O7-P

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ANYAA9 Annals of the New York Academy of Sciences. (New York Academy of Sciences, 2 E. 63rd St., New York, NY 10021) V.1- 1877- Volume(issue)/page/year: 60,251,1954

 Safety Information

RIDADR NONH for all modes of transport
WGK Germany 3
RTECS AU7480300

 Synthetic Route

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 Synonyms

Adenosine Monophosphate Hydrate (2'- and 3'- mixture) from Yeast
MFCD00151215
Adenosine 2'-monophosphate
Adenylic Acid Hydrate (2'- and 3'- mixture) from Yeast
Methionyl adenylate
adenosine 2'-monophosphoric acid
Adenosine 2'(3')-monophosphate mixed isomers
Adenosine 2'-phosphate
2'(3')-AMP Hydrate (2'- and 3'- mixture) from Yeast
Methioninyl adenylate
2'-Adenylic acid
EINECS 204-990-7
L-METHIONYL ADENYLATE
2'-adenosine monophosphate