01890

Adenosine

• Sinónimos: 9-β-D-Ribofuranosyladenine, Adenine riboside, Adenine-9-β-D-ribofuranoside
• Fórmula empírica (notación de Hill): C₁₀H₁₃N₅O₄
• Número de CAS: 58-61-7
• Peso molecular: 267.24
• Beilstein: 93029
• Número CE: 200-389-9
• Número MDL: MFCD00005752
• Código UNSPSC: 12352200
• eCl@ss: 32160413
• ID de la sustancia en PubChem: 329747369
• NACRES: NA.77

Propiedades

• Formulario: powder
• Nivel de calidad: 200
• actividad óptica: [α]20/D −70±3°, c = 2% in 5% NaOH
• residuo de ign.: ≤0.1% (as SO₄)
• mp: 234-236 °C (lit.)
• trazas de catión: 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
• temp. de almacenamiento: 2-8°C
• cadena SMILES: Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O; 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
• Clave InChI: OIRDTQYFTABQOQ-KQYNXXCUSA-N
• Información sobre el gen: human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)

Descripción

Descripción general

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.

Aplicación

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

Acciones bioquímicas o fisiológicas

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).

Otras notas

Substrate for the assay of adenosine deaminase

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 2
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Gloves, type N95 (US)