Adenosine
[CAS# 58-61-7]

Identification

• Classification: Biochemical >> Nucleic acid drug
• Name: Adenosine
• Synonyms: 9-beta-D-Ribofuranosyladenine; Adenine riboside; Adenine-9-beta-D-ribofuranoside
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.24
• CAS Registry Number: 58-61-7
• EC Number: 200-389-9
• SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N

Properties

• Solubility: 10 mM (DMSO)
• Melting point: 234-236 °C
• alpha: -70

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Adenosine is a key nucleoside in biochemistry and medicine, essential for many physiological processes and biochemical reactions. Adenosine is composed of adenine and ribose, and plays a key role in energy transfer and signaling within cells.

Adenosine was first discovered in the early 20th century during the study of nucleic acids and cellular respiration as scientists explored the biochemical composition of cells and their role in energy transfer, revealing its fundamental role in the metabolism of all organisms. Its name is derived from "adenine" and "sugar" (ribose), reflecting its structure as a combination of these two components.

Adenosine is an important component of adenosine triphosphate (ATP), the main energy carrier in cells. ATP is composed of adenine, ribose, and three phosphate groups, and is essential for cellular processes, including muscle contraction, protein synthesis, and cell division. Adenosine itself, released during the breakdown of ATP, can act as a signaling molecule to regulate energy metabolism and maintain cellular function.

In medicine, adenosine has therapeutic applications due to its effects on the cardiovascular system. It is used as an antiarrhythmic agent to treat certain types of abnormal heart rhythms, such as paroxysmal supraventricular tachycardia (PSVT). Adenosine works by temporarily slowing electrical conduction in the heart's atrioventricular (AV) node, helping to restore normal heart rhythm.

Adenosine plays an important role in the central nervous system as a neuromodulator. It is involved in a variety of physiological processes, including sleep regulation, pain modulation, and neuroprotection. Adenosine receptors, particularly the A1 and A2A subtypes, are targets for drugs that treat sleep disorders, chronic pain, and neurodegenerative diseases. For example, caffeine acts as an adenosine receptor antagonist, promoting wakefulness by blocking the inhibitory effects of adenosine.

Adenosine's role in regulating immune responses and cell proliferation makes it a target for cancer research. Tumor cells often exploit adenosine signaling to evade immune detection and promote tumor growth. Researchers are exploring adenosine receptor antagonists and inhibitors of adenosine production as potential therapeutic strategies to enhance antitumor immunity and improve cancer treatment.

References

2025. Adenosine regulates depressive behavior in mice with chronic social defeat stress through gut microbiota. Neuropharmacology.
DOI: 10.1016/j.neuropharm.2024.110209

2025. Purinergic signaling in the battlefield of viral infections. Purinergic Signalling.
DOI: 10.1007/s11302-023-09981-8

2025. Direct and quantitative analysis of tRNA acylation using intact tRNA liquid chromatography-mass spectrometry. Nature Protocols.
DOI: 10.1038/s41596-024-01086-9