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01890

Adenosine

Sinónimos:

9-β-D-Ribofuranosyladenine, Adenine riboside, Adenine-9-β-D-ribofuranoside

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Fórmula empírica (notación de Hill):
C10H13N5O4
Número CAS:
58-61-7
Peso molecular:
267.24
PubChem Substance ID:
329747369
eCl@ss:
32160413
UNSPSC Code:
12352200
NACRES:
NA.77
EC Number:
200-389-9
MDL number:
MFCD00005752
Beilstein/REAXYS Number:
93029
Form:
powder
Servicio técnico
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form

powder

Quality Level

200

optical activity

[α]20/D −70±3°, c = 2% in 5% NaOH

ign. residue

≤0.1% (as SO4)

mp

234-236 °C (lit.)

cation traces

Ca: ≤10 mg/kg, Cd: ≤5 mg/kg, Co: ≤5 mg/kg, Cr: ≤5 mg/kg, Cu: ≤5 mg/kg, Fe: ≤5 mg/kg, Mg: ≤20 mg/kg, Mn: ≤5 mg/kg, Ni: ≤5 mg/kg, Pb: ≤5 mg/kg, Zn: ≤5 mg/kg

storage temp.

2-8°C

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChI key

OIRDTQYFTABQOQ-KQYNXXCUSA-N

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)

General description

Adenosine is a purine nucleoside base. It consists of adenine bound to a ribose sugar molecule via a glycosidic bond. Adenosine is found intracellularly and extracellularly in living cells. It acts as a precursor and as a metabolite of adenine nucleotides. In all living organisms, adenosine acts as an essential structural factor for adenosinetriphosphate (ATP), adenosine diphosphate (ADP), and cyclic adenosine monophosphate (cAMP), thereby playing an important role in energy transfer. Adenosine plays a crucial role in the central nervous system, endocrine system, inflammatory and immune response, and cardiovascular system. It is an important endogenous modulator of kidney function, lung function, pain, and sleep via the activation of adenosine receptors.

Application

Adenosine has been used as a standard to determine the adenosine content in whole heart samples from mice.

Biochem/physiol Actions

Endogenous neurotransmitter at adenosine receptors. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti−inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).
Endogenous neurotransmitter. Cardioprotective effects may relate to activation of A1 adenosine receptors. The antiplatelet and anti−inflammatory actions of adenosine appear to be mediated via the A2 adenosine receptor. In contrast, adenosine appears to be a pro-inflammatory mediator in asthma and chronic obstructive pulmonary disease (COPD).

Other Notes

Substrate for the assay of adenosine deaminase

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Clase de almacenamiento

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
WXBF7474V
BCCJ2756
BCCB5275
BCBW9915
BCBV4960

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Elizabeth A Vecchio et al.
Pharmacology & therapeutics, 198, 20-33 (2019-01-25)
The adenosine A2B receptor (A2BAR) is one of four adenosine receptor subtypes belonging to the Class A family of G protein-coupled receptors (GPCRs). Until recently, the A2BAR remained poorly characterised, in part due to its relatively low affinity for the
P. Nygaard
Methods in Enzymology, 508-508 null
Ming Cai et al.
Journal of molecular and cellular cardiology, 51(6), 927-935 (2011-09-24)
Modulation of purinergic signaling is critical to myocardial homeostasis. Ectonucleoside triphosphate diphosphohydrolase 1 (ENTPD-1; CD39) which converts the proinflammatory molecules ATP or ADP to AMP is a key regulator of purinergic modulation. However, the salutary effects of transgenic over expression
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