Chemicals and Drugs

Caffeine

A methylxanthine naturally occurring in some beverages and also used as a pharmacological agent. Caffeine's most notable pharmacological effect is as a central nervous system stimulant, increasing alertness and producing agitation. It also relaxes SMOOTH MUSCLE, stimulates CARDIAC MUSCLE, stimulates DIURESIS, and appears to be useful in the treatment of some types of headache. Several cellular actions of caffeine have been observed, but it is not entirely clear how each contributes to its pharmacological profile. Among the most important are inhibition of cyclic nucleotide PHOSPHODIESTERASES, antagonism of ADENOSINE RECEPTORS, and modulation of intracellular calcium handling.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A methylxanthine naturally occurring in some beverages and also used as a pharmacological agent. Caffeine's most notable pharmacological effect is as a central nervous system stimulant, increasing alertness and producing agitation. It also relaxes SMOOTH MUSCLE, stimulates CARDIAC MUSCLE, stimulates DIURESIS, and appears to be useful in the treatment of some types of headache. Several cellular actions of caffeine have been observed, but it is not entirely clear how each contributes to its pharmacological profile. Among the most important are inhibition of cyclic nucleotide PHOSPHODIESTERASES, antagonism of ADENOSINE RECEPTORS, and modulation of intracellular calcium handling.

Chemical Identity

Chemical Information

Molecular Formula
C8H10N4O2
Molecular Weight
194.19 g/mol
CAS Registry No.
58-08-2
IUPAC Name
1,3,7-trimethylpurine-2,6-dione
InChIKey
RYYVLZVUVIJVGH-UHFFFAOYSA-N
SMILES
CN1C=NC2=C1C(=O)N(C(=O)N2C)C
MeSH Unique ID
D002110
Source
PubChem CID 2519

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

See Also

MeSH Record

Synonyms

13 entry terms
  • 1,3,7-Trimethylxanthine
  • Caffedrine
  • Coffeinum N
  • Coffeinum Purrum
  • Dexitac
  • Durvitan
  • No Doz
  • Percoffedrinol N
  • Percutaféine
  • Quick-Pep
  • Vivarin
  • Quick Pep
  • QuickPep

MeSH Record

Aspects Covered

27 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Hierarchy

Tree Numbers

  1. D03w.132w.960.175w
  2. D03w.633.100.759.758w.824.175w

MeSH Record

NLM Classification

QV 107

AMA Style

References

  1. National Library of Medicine. Caffeine. Medical Subject Headings (MeSH). 2026. Unique ID D002110. http://id.nlm.nih.gov/mesh/2026/D002110
  2. Caffeine. In: Wikipedia. https://en.wikipedia.org/wiki/Caffeine
  3. Caffeine. In: Wikidata. https://www.wikidata.org/wiki/Q60235
  4. Caffeine. In: PubChem Compound. CID 2519. https://pubchem.ncbi.nlm.nih.gov/compound/2519