Adenine
[CAS# 73-24-5]

Identification

• Classification: API >> Vitamins and minerals >> Vitamin B drugs
• Name: Adenine
• Synonyms: 6-Aminopurine ; Vitamin B4; Vitamin B4; 6-Aminopurine
• Molecular Formula: C₅H₅N₅
• Molecular Weight: 135.13
• CAS Registry Number: 73-24-5
• EC Number: 200-796-1
• SMILES: C1=NC2=NC=NC(=C2N1)N

Properties

• Melting point: 360-365 °C
• Sublimation: 220 °C
• Water solubility: 0.5 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H301
• Safety Statements: P264-P270-P301+P316-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Adenine is one of the four primary nucleobases found in the nucleic acids DNA and RNA, playing a fundamental role in the storage and transmission of genetic information. It is a purine derivative, consisting of a fused double-ring structure composed of a six-membered and a five-membered nitrogen-containing ring. Chemically, adenine is classified as 6-aminopurine, reflecting the amino group attached to the purine ring.

The discovery of adenine dates back to the late 19th century when it was first isolated from nucleic acids. Its structure was elucidated in the early 20th century through advances in organic chemistry and crystallography. Adenine is naturally synthesized in living organisms through metabolic pathways involving the purine biosynthesis cycle.

Adenine’s primary biological function is as a fundamental building block of nucleotides. In DNA and RNA, adenine pairs with thymine (in DNA) or uracil (in RNA) via hydrogen bonding, contributing to the stability of the double helix structure and the faithful replication of genetic material. Adenine nucleotides such as adenosine triphosphate (ATP), adenosine diphosphate (ADP), and adenosine monophosphate (AMP) are central to cellular energy transfer, signaling, and metabolism.

Beyond its genetic role, adenine forms part of several coenzymes and signaling molecules. These include nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD), and cyclic adenosine monophosphate (cAMP), which are vital for redox reactions, enzymatic activity, and intracellular signal transduction.

In addition to its biological significance, adenine is utilized in biochemical research and biotechnology. It serves as a fundamental component in the synthesis of oligonucleotides, primers for polymerase chain reactions (PCR), and in studies of nucleic acid structure and function.

The chemical synthesis of adenine has been achieved through various laboratory methods, enabling its production for research and industrial purposes. In prebiotic chemistry, adenine has been studied as a potential compound formed under early Earth conditions, highlighting its importance in theories of the origin of life.

In summary, adenine is a purine nucleobase discovered in the late 19th century, integral to the structure and function of nucleic acids. It participates in genetic information storage, cellular energy metabolism, and enzymatic reactions, making it indispensable to life. Its applications extend to molecular biology research and understanding the biochemical foundations of living systems.

References

2018. Effect of Sevelamer on Serum Levels of Klotho and Soluble Tumor Necrosis Factor-like Weak Inducer of Apoptosis in Rats With Adenine-induced Chronic Kidney Disease. Iranian journal of kidney diseases, 12(5).
URL: https://pubmed.ncbi.nlm.nih.gov/30367019

2019. Single step grown MoS2 on pencil graphite as an electrochemical sensor for guanine and adenine: A novel and low cost electrode for DNA studies. Biosensors and Bioelectronics, 124-125.
DOI: 10.1016/j.bios.2018.08.055

2019. Rapid plant regeneration in industrially important Curcuma zedoaria revealing genetic and biochemical fidelity of the regenerants. 3 Biotech, 9(12).
DOI: 10.1007/s13205-019-2009-9