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Merck

01890

Adenosine

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
58-61-7
Molecular Weight:
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

Key Documents

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SMILES string

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 key

OIRDTQYFTABQOQ-KQYNXXCUSA-N

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

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

Quality Level

200

Gene Information

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

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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).

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.

Other Notes

Substrate for the assay of adenosine deaminase

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB5275
BCBW9915
BCBV4960
BCBR8018V
BCBQ9790V

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Adenosine deaminase from human erythrocytes.
R P Agarwal et al.
Methods in enzymology, 51, 502-507 (1978-01-01)
P. Nygaard
Methods in Enzymology, 508-508 null
R W Jansen et al.
Hepatology (Baltimore, Md.), 18(1), 146-152 (1993-07-01)
We covalently coupled 9-beta-D-arabinofuranosyladenine 5'-monophosphate (ara-AMP) to the carrier molecule lactosaminated human serum albumin using a water-soluble carbodiimide with a two-step conjugation method (pH 4.5 and pH 7.5) instead of the commonly used single-step conjugation at pH 7.5. This resulted
Deepak Mittal et al.
Cancer research, 74(14), 3652-3658 (2014-07-06)
Adenosine targeting is an attractive new approach to cancer treatment, but no clinical study has yet examined adenosine inhibition in oncology despite the safe clinical profile of adenosine A2A receptor inhibitors (A2ARi) in Parkinson disease. Metastasis is the main cause
S W Jansen et al.
Scientific reports, 5, 11525-11525 (2015-06-20)
Few studies have included subjects with the propensity to reach old age in good health, with the aim to disentangle mechanisms contributing to staying healthier for longer. The hypothalamic-pituitary-thyroid (HPT) axis maintains circulating levels of thyroid stimulating hormone (TSH) and
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