Adenosine is a purine nucleoside that occurs naturally in all living cells and is a homeostatic bioenergetic regulator of cardiac, nervous system and skeletal muscle function. Its half-life in human blood is approximately 10 seconds, but it is a powerful vasodilator.

Industrially it appears in the form of a fine white powder. 

What it is used for and where

Medical

Caffeine is an adenosine A and can therefore be considered a co-factor in the treatment of certain neurological disorders. Conversely, adenosine is also known to counteract insomnia and reduce convulsions.

Adenosine can mitigate intoxication, sedation, motor coordination disorders due to the effects of alcohol and help limit many of the different effects of alcohol on the brain and other organ systems in the body (1). Furthermore, in view of the protective properties of adenosine, this nucleoside may play the role of a cardioprotector (2).

Scientific research has gone even further and investigated the possibilities of adenosine and its analogues as anti-cancer drugs (3).

Used in the treatment of angina, coronary dysfunction, cerebrovascular disorders, atherosclerosis, hypertension, progressive muscular atrophy, etc.,

Cosmetics

Adenosine applied in cream or patch form has demonstrated a skin-improving effect and is considered a new, safe and effective cosmetic to improve wrinkles, dermal density, elasticity and skin hydration (4) confirming, in 2018, the results of this 2007 study on the anti-wrinkle effect induced by the application of a soluble film containing adenosine (5).

Other applications

It is an important intermediate component for synthesising adenine, adenosine triphosphate, adenylate and adenosine arabinase.

Adenosina studies

Caratteristiche tipiche ottimali del prodotto commerciale  Adenosine

• Molecular Formula  C₁₀H₁₃N₅O₄
• Molecular Weight     267.24
• Exact Mass   267.096741
• CAS  58-61-7
• UNII    K72T3FS567
• EC Number   200-389-9
• DSSTox Substance ID  DTXSID1022558
• IUPAC  (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• 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  
• InChl Key      OIRDTQYFTABQOQ-KQYNXXCUSA-N
• SMILES   C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
• MDL number   MFCD00005752
• PubChem Substance ID    24277685
• ChEBI  16335
• Beilstein    93029
• NSC   755857
• eCl@ss     32160413
• NACRES  NA.77   
• NCI   C207

Synonyms:

• (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Adenocard
• Adenoscan
• 9-beta-D-Ribofuranosyladenine

References_______________________________________________________________________

(1) Dohrman DP, Diamond I, Gordon AS. The role of the neuromodulator adenosine in alcohol's actions. Alcohol Health Res World. 1997;21(2):136-43.

(2) Riksen NP, Rongen GA, Yellon D, Smits P. Human in vivo research on the vascular effects of adenosine. Eur J Pharmacol. 2008 May 13;585(2-3):220-7. doi: 10.1016/j.ejphar.2008.01.053. 

(3) Man S, Lu Y, Yin L, Cheng X, Ma L. Potential and promising anticancer drugs from adenosine and its analogs. Drug Discov Today. 2021 Jun;26(6):1490-1500. doi: 10.1016/j.drudis.2021.02.020. 

(4) Kang G, Tu TNT, Kim S, Yang H, Jang M, Jo D, Ryu J, Baek J, Jung H. Adenosine-loaded dissolving microneedle patches to improve skin wrinkles, dermal density, elasticity and hydration. Int J Cosmet Sci. 2018 Apr;40(2):199-206. doi: 10.1111/ics.12453.

(5) Legendre JY, Schnitzler I, Li QY, Hausen C, Huart M, Luengo GS, Abella ML, Roreger M. Formulation, characterization, and efficacy of an adenosine-containing dissolvable film for a localized anti-wrinkle effect. J Cosmet Sci. 2007 Mar-Apr;58(2):147-55. 

Compendium of the most significant studies with reference to properties, intake, effects.

Legendre JY, Schnitzler I, Li QY, Hausen C, Huart M, Luengo GS, Abella ML, Roreger M. Formulation, characterization, and efficacy of an adenosine-containing dissolvable film for a localized anti-wrinkle effect. J Cosmet Sci. 2007 Mar-Apr;58(2):147-55.

Abstract. A randomized, placebo-controlled, investigator-blind study was conducted in female volunteers to assess the efficacy of the 1% adenosine-containing dissolvable film.

Simpson RE, Phillis JW. Adenosine in exercise adaptation. Br J Sports Med. 1992 Mar;26(1):54-8. doi: 10.1136/bjsm.26.1.54.

Abstract. By influencing the regulation of the mechanisms of angiogenesis, erythropoietin production, blood flow, myocardial glucose uptake, glycogenolysis, systolic blood pressure, respiration, plasma norepinephrine and epinephrine levels, adenosine may exert a significant effect on the body's adaptation response to exercise.

Masino SA, Kawamura M Jr, Cote JL, Williams RB, Ruskin DN. Adenosine and autism: a spectrum of opportunities. Neuropharmacology. 2013 May;68:116-21. doi: 10.1016/j.neuropharm.2012.08.013.

Abstract. Because adenosine is a broad homeostatic regulator of cell function and nervous system activity, increasing adenosine's influence might be a new therapeutic target for autism with multiple beneficial effects. This article is part of the Special Issue entitled 'Neurodevelopmental Disorders'.

Mou KJ, Shen KF, Li YL, Wu ZF, Duan W. Adenosine A2A Receptor in Bone Marrow-Derived Cells Mediated Macrophages M2 Polarization via PPARγ-P65 Pathway in Chronic Hypoperfusion Situation. Front Aging Neurosci. 2022 Jan 3;13:792733. doi: 10.3389/fnagi.2021.792733.

Abstract. The role of adenosine A2A receptor (A2AR) in the ischemic white matter damage induced by chronic cerebral hypoperfusion remains obscure. Here we investigated the role of A2AR in the process of macrophage polarizations in the white matter damage induced by chronic cerebral hypoperfusion and explored the involved signaling pathways.

Pelleg A, Porter RS. The pharmacology of adenosine. Pharmacotherapy. 1990;10(3):157-74.

Abstract.   Exogenous adenosine has a wide spectrum of effects in experimental animal models as well as humans. The pharmacokinetics, pharmacodynamics, and the interaction of adenosine with other drugs are reviewed.

Kaster MP, Machado DG, Santos AR, Rodrigues AL. Involvement of NMDA receptors in the antidepressant-like action of adenosine. Pharmacol Rep. 2012;64(3):706-13. doi: 10.1016/s1734-1140(12)70865-4.

Abstract. In this work, the contribution of NMDA receptors to the antidepressant-like effect of adenosine in the forced swimming test (FST) was investigated.

Nakav S, Kachko L, Vorobiov M, Rogachev B, Chaimovitz C, Zlotnik M, Douvdevani A. Blocking adenosine A2A receptor reduces peritoneal fibrosis in two independent experimental models. Nephrol Dial Transplant. 2009 Aug;24(8):2392-9. doi: 10.1093/ndt/gfp041.

Abstract. Long-term peritoneal dialysis (PD) is associated with peritoneal fibrosis and loss of function. It has been shown that activation of the adenosine A(2A) receptor (A(2A)R) promotes tissue repair, wound healing and extracellular matrix (ECM) production. We have previously shown that adenosine is a potent regulator of inflammation in the peritoneum. In the current study, we explored the role of adenosine and the A(2A)R in two experimental models.