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Structural formula
Structural formula of adenosine
Non-proprietary name Adenosine
other names
  • A (short code)
  • 9-β- D- ribofuranosyladenine
  • 9 - [(2 R , 3 R , 4 S , 5 R ) -3,4-dihydroxy-5- (hydroxymethyl) oxolan-2-yl] -6-aminopurine
  • Ado
Molecular formula C 10 H 13 N 5 O 4
Brief description

white and odorless solid

External identifiers / databases
CAS number 58-61-7
EC number 200-389-9
ECHA InfoCard 100,000,354
PubChem 60961
ChemSpider 54923
DrugBank DB00640
Wikidata Q190012
Drug information
ATC code

C01 EB10

Drug class


Molar mass 267.24 g mol −1
Physical state



0.31 g cm −3

Melting point

234-237 ° C

  • practically insoluble in ethanol
  • soluble in hot water
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

> 20 g kg −1 ( LD 50mouseoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Adenosine (A, Ado) is a nucleoside and consists of the nucleic base adenine and the sugar β- D- ribose . The analogue with deoxyribose is deoxyadenosine . It is part of the energy-rich compounds ATP , ADP , AMP , ribonucleic acid (RNA), various cofactors (e.g. coenzyme A , NADPH , NADH ) and also in a neuromodulator .


Adenosine is a white and odorless solid that practically does not dissolve in ethanol, but is soluble in hot water.

Biological importance

Adenosine is part of ribonucleic acid (RNA) and forms a base pair there with uridine , dihydrouridine or pseudouridine .

Base pair AU.svg Base pair AD.svg Base pair APsi.svg
AU base pair AD base pair A Ψ base pair

Pharmaceutical importance


Adenosine blocks the release of all invigorating and activating neurotransmitters such as dopamine , acetylcholine or norepinephrine . This causes dilation (widening of the blood vessels), which lowers blood pressure. Adenosine also lowers the heart rate and increases the conduction time in the AV node . This is done by activating a G i -modulated potassium channel via A 1 adenosine receptors.

Adenosine also triggers the nucleus praeopticus ventrolateralis in the hypothalamus , which inhibits the waking and waking centers of the brain through the neurotransmitter GABA , and thus has a sleep-inducing effect . The xanthines caffeine , theobromine and theophylline as well as the artificial drug istradefylline act as antagonists of various adenosine receptors . Partial inhibition of the receptors in the nucleus praeopticus ventrolateralis also contributes to their sleep-suppressing effect.


Adenosine is indicated for the termination of AV nodal reentry tachycardia . It blocks the conduction of excitation from the atrium to the ventricle , causing a cardiac arrest lasting a few seconds. The physiological half-life ( half-life ) of adenosine is in the range of seconds. With theophylline one exists antidote .

Adenosine is predominantly used for the pharmacological exposure of myocardial scintigraphy .

Commercial preparations


Adenoscan (D), Adrekar (D), Krenosin (CH), Generics (D, A)

Combination preparations

ViaSpan organ preservation solution (A), Vita-Gerin "Geistlich" (A)

Related links

Web links

Commons : Adenosine  - Collection of pictures, videos and audio files
Commons : Adenosine derivatives  - collection of pictures, videos and audio files
  • Entry for adenosine in the Human Metabolome Database (HMDB) , accessed October 21, 2013.
  • Modification Summary of Adenosine in the Modomics database, accessed January 13, 2014.

Individual evidence

  1. Entry on ADENOSINE in the CosIng database of the EU Commission, accessed on March 26, 2020.
  2. a b c d e data sheet adenosine (PDF) from Carl Roth , accessed on November 28, 2013.
  3. a b Wissenschaft-Online-Lexika: Entry on adenosine in the Lexikon der Chemie ; Retrieved November 28, 2013.
  4. C. Cajochen: Sleep Regulation . In: Somnologie - Schlafforschung und Schlafmedizin, Volume 13, Number 2, June 2009, pp. 64–71 ( doi : 10.1007 / s11818-009-0423-7 ).
  5. Wolfgang Hauber: Adenosine: a purine nucleoside with neuromodulatory effects. Neuroforum 3/02, pp. 228-234 ( PDF , 212 kB).