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Structural formula
Structure of adenine
Surname Adenine
other names
  • 9 H -purine-6-amine ( IUPAC name)
  • 6-aminopurine
Molecular formula C 5 H 5 N 5
Brief description

light yellow solid

External identifiers / databases
CAS number 73-24-5
EC number 200-796-1
ECHA InfoCard 100,000,724
PubChem 190
ChemSpider 185
DrugBank DB00173
Wikidata Q15277
Drug information
ATC code

A11 HA

Molar mass 135.13 g mol −1
Physical state


boiling point

Decomposition from 360 ° C

Sublimation point

220 ° C


poor in water (0.5 g l −1 at 20 ° C)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic


H and P phrases H: 301
P: 301 + 310 + 330
Toxicological data

227 mg kg −1 ( LD 50ratoral )

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

Adenine is one of the four nucleobases in DNA and in RNA , alongside cytosine , guanine and thymine or uracil (in RNA).

It is a heterocyclic organic compound with a purine backbone and an amino group in the 6-position. The deoxyadenosine in DNA and the adenosine in RNA are nucleosides that contain adenine. With thymine or uracil it forms two hydrogen bonds in the Watson-Crick base pairing .


History and biological meaning

On January 12, 1885, the later Nobel Prize winner Albrecht Kossel reported to the Berlin Chemical Society about an important discovery. He was able to isolate a nitrogen-rich base with the empirical formula C 5 H 5 N 5 , for which he derived from the Greek , from a large amount of bovine pancreas, which had been processed by Adolph Bannow (1844-1919) in the Berlin chemical plant Kahlbaum Word "aden" for gland, the name adenine suggested. Kossel also proved it to be a cleavage product of the yeast nuclein. He was later able to detect adenine as a cleavage product of the nucleic acid.

Adenine can be part of DNA, RNA or various nucleosides and nucleotides .


Via the N 9 atom of the five-membered ring, adenine can be bound N -glycosidically to the C 1 atom of the ribose ; one then speaks of a nucleoside , the adenosine . When binding to deoxyribose , the nucleoside deoxyadenosine is formed . In contrast to most nucleosides, the synthetic vidarabine contains arabinose instead of ribose .

Adenosine.svg Deoxyadenosine.svg Vidarabine.svg
Adenosine, A. Deoxyadenosine, dA Vidarabin, araA


Phosphoric acid can be bound to adenosine as a phosphate residue, which is how it is formed

Corresponding molecules are formed when the phosphate residues are bound to deoxyadenosine (dAMP; dADP; dATP).

Adenosine triphosphate (ATP) plays a special role in the cell's energy metabolism . The reaction ATP → ADP + P releases energy ; the reaction ADP + P → ATP stores energy chemically.

Cyclic adenosine monophosphate (cAMP) is a very common second messenger for cellular signal transduction .

Adenine is also part of the nicotinamide adenine dinucleotide NAD + , which serves as a coenzyme for hydrogen transfer and thus participates in redox reactions in the cell . Adenine is used for the biosynthesis of the coenzyme S-adenosyl-methionine , which is used in biological methylations , e.g. B. by a Dam methylase .

Part of DNA and RNA

Adenine forms two hydrogen bonds with thymidine in the DNA double helix . During transcription, however, the adenine of the codogenic strand of DNA pairs with the uridine of the mRNA that has just been formed . There are also pairings with dihydrouridine or pseudouridine in the tRNA .

Base pair AT.svg Base pair AU.svg Base pair AD.svg Base pair APsi.svg
AT base pair (DNA) AU base pair (RNA) AD base pair (RNA) A Ψ base pair (RNA)

Related links

1-Methyladenine.svg 2-methyladenine.svg 6-methyladenine.svg 6-Dimethylaminopurine.svg N6-Isopentenyladenine.svg 2-aminopurine.svg
1-methyladenine 2-methyladenine N 6 -methyladenine N 6 , N 6 -dimethyladenine N 6 isopentenyladenine 2-aminopurine (isoadenine)

Web links

Commons : Adenine  - Collection of images, videos and audio files
Commons : Adenine derivatives  - collection of images, videos and audio files
Wiktionary: Adenine  - explanations of meanings, word origins, synonyms, translations
  • Entry for adenines in the Human Metabolome Database (HMDB) , accessed November 19, 2013.

Individual evidence

  1. entry to ADENINE in CosIng database of the European Commission, accessed on 27 March 2020th
  2. Adenine data sheet (PDF) from Carl Roth , accessed on December 14, 2010.
  3. a b entry on adenine. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.
  4. a b c Entry on adenine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  5. Adenine data sheet from Sigma-Aldrich , accessed on October 16, 2016 ( PDF ).
  6. ^ Albert Gossauer, Structure and Reactivity of Biomolecules: An Introduction to Organic Chemistry, Verlag Helvetica Chimica Acta, 2006 .
  7. Kossel, A .: About a new base from the animal body. Lecture in: Reports of the German Chemical Society , Issue 18, 1885, p. 79.
  8. ^ Kossel, A .: Further contributions to the chemistry of the cell nucleus. In: Zeitschrift für Physiologische Chemie , Volume 10, 1886, p. 248.
  9. Kossel, A .: About the chemical composition of the cell. Lecture in: Archives for Anatomy and Physiology. Physiological Department , 1891, p. 178.