01890

Adenosine

• Synonyme(s) : 9-β-D-Ribofuranosyladenine, Adenine riboside, Adenine-9-β-D-ribofuranoside
• Formule empirique (notation de Hill): C₁₀H₁₃N₅O₄
• Numéro CAS: 58-61-7
• Poids moléculaire : 267.24
• Numéro Beilstein : 93029
• Numéro CE : 200-389-9
• Numéro MDL: MFCD00005752
• Code UNSPSC : 12352200
• eCl@ss : 32160413
• ID de substance PubChem : 329747369
• Nomenclature NACRES : NA.77

Propriétés

• Forme: powder
• Activité optique: [α]20/D −70±3°, c = 2% in 5% NaOH
• Résidus de calcination: ≤0.1% (as SO₄)
• Pf: 234-236 °C (lit.)
• Traces de cations: 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
• Température de stockage: 2-8°C
• Chaîne SMILES: 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
• Clé InChI: OIRDTQYFTABQOQ-KQYNXXCUSA-N
• Informations sur le gène: human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)

Description

Description générale

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.

Actions biochimiques/physiologiques

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).

Autres remarques

Substrate for the assay of adenosine deaminase

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 2
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)