Adenosine

Catalog	BBC58617
CAS	58-61-7
Structure
Synonyms	Adenine-9-1'-β-ribofuranoside
IUPAC Name	(2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Molecular Weight	267.24
Molecular Formula	C10H13N5O4
Canonical SMILES	C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
InChI	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
Boiling Point	410.43 °C
Melting Point	234-236 °C(lit.)
Purity	99%
Density	1.3382 g/cm³
Solubility	Soluble in water, ammonium hydroxide, dimethyl sulfoxide, insoluble in ethanol
Appearance	White crystalline powder
Storage	2-8 °C
Active Content	95%
pKa	pK1:3.6, pK2:12.4 (25°C)
Refractive Index	1.7610

Case Study

Role Of Adenosine In The Central Nervous System

Dunwiddie, Thomas V., and Susan A. Masino. Annual review of neuroscience 24.1 (2001): 31-55.

Adenosine is a modulator with a general and ubiquitous inhibitory effect on neuronal activity. Tonic activation of adenosine receptors by adenosine, which is normally present in the extracellular space of brain tissue, results in an inhibitory effect that appears to be mediated by adenosine A and A receptors. Relief of this tonic inhibition by receptor antagonists is responsible for the excitatory effects of these drugs. Characterization of the actions of adenosine receptor agonists and antagonists has led to many hypotheses regarding the actions of this nucleoside.
Adenosine participates in a variety of functions in the central nervous system. Although in a general sense many of its actions are inhibitory, consistent with its role as an endogenous anticonvulsant, neuroprotectant, and sleep-inducing factor, this depends on the brain system and complement of adenosine receptors present. There is little evidence that adenosine is a neurotransmitter; rather, it appears to be a neuromodulator that is released in some unconventional manner to modulate and regulate neuronal activity. A current challenge in the field is to better define the mechanisms of adenosine release in response to both pathological and nonpathological stimuli.