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/REAXYS Number: 93029
• EC Number: 200-389-9
• MDL number: MFCD00005752
• UNSPSC Code: 12352200
• eCl@ss: 32160413
• PubChem Substance ID: 329747369
• NACRES: NA.77

Propiedades

• form: powder
• 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)

Descripción

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).

Other Notes

Substrate for the assay of adenosine deaminase

Información de seguridad

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)