File:Caffeine_structure.svg · Wikimedia Commons · See Wikimedia Commons
caffeine
Sign in to saveAlso known as methyltheobromine, 1,3,7-trimethyl-2,6-dioxopurine, 1,3,7-trimethylxanthine, theine, 7-methyltheophylline, 1-methyltheobromine, guaranine, 1,3,7-trimethylpurine-2,6-dione
Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class and is the most commonly consumed psychoactive substance globally. It is mainly used for its eugeroic (wakefulness promoting), ergogenic (physical performance-enhancing), or nootropic (cognitive-enhancing) properties; it is also used recreationally or in social settings. Caffeine acts by blocking the binding of adenosine at a number of adenosine receptor types, inhibiting the centrally depressant effects of adenosine and enhancing the release of acetylcholine. Caffeine has a three-dimensional structure similar to
OverviewAI-generated
Caffeine is a chemical compound with the formula C₈H₁₀N₄O₂. Its IUPAC name is 1,3,7-trimethylpurine-2,6-dione. The substance has a mass of 194.08037556 and a density of 1.23. It melts at 235 and sublimes at 180. The pKa is 14, and the electric dipole moment is 3.64.
Chemical properties include an xlogp of -0.1 and a topological polar surface area of 58.4. The molecule has zero hydrogen bond donors and three hydrogen bond acceptors, with a charge of 0. The canonical SMILES representation is CN1C=NC2=C1C(=O)N(C(=O)N2C)C.
Caffeine is referenced by 3,330 other encyclopedia articles. A PubMed query for caffeine yields 42,555 results. The MCN code for the compound is 2939.30.10.
Synthesized by Vinony from 25 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.image
- Caffeine structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 187
- Drug.alt
- 2D structure of caffeine
- Drug.image_class2
- bg-transparent
- Drug.alt2
- 3D structure of caffeine
- Drug.imageL
- Caffeine molecule ball from xtal (1).png
- Drug.image_classL
- bg-transparent
- Drug.imageR
- Caffeine molecule spacefill from xtal (1).png
- Drug.image_classR
- bg-transparent
- Drug.DailyMedID
- Caffeine
- Drug.pregnancy_AU
- A
- Drug.dependency_liability
- Physical: Low–moderate (9–30%) Psychological: Low–moderate
- Drug.addiction_liability
- Low (9%)
- Drug.routes_of_administration
- Common: By mouth Medical: Intravenous Uncommon: Insufflation, rectal, transdermal, topical, buccal, sublingual
- Drug.class
- Stimulant;Adenosinergic; Eugeroic;Nootropic;Anxiogenic; Analeptic; PDE inhibitor;Diuretic
- Drug.ATC_prefix
- N06B
- Drug.ATC_suffix
- C01
via Wikipedia infobox
Chemical data
- Formula
- C8H10N4O2
- Molecular weight
- 194.19 g/mol
- IUPAC name
- 1,3,7-trimethylpurine-2,6-dione
- SMILES
- CN1C=NC2=C1C(=O)N(C(=O)N2C)C
- InChIKey
- RYYVLZVUVIJVGH-UHFFFAOYSA-N
- XLogP
- -0.1
- Polar surface area
- 58.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
42,555 papers- Caffeine: cognitive and physical performance enhancer or psychoactive drug?ReviewCurrent neuropharmacology · 2015Cappelletti S, Piacentino D, Sani G et al.DOI: 10.2174/1570159X13666141210215655
- Common questions and misconceptions about caffeine supplementation: what does the scientific evidence really show?ReviewJournal of the International Society of Sports Nutrition · 2024Antonio J, Newmire DE, Stout JR et al.DOI: 10.1080/15502783.2024.2323919
- A review of caffeine's effects on cognitive, physical and occupational performance.ReviewNeuroscience and biobehavioral reviews · 2016McLellan TM, Caldwell JA, Lieberman HRDOI: 10.1016/j.neubiorev.2016.09.001
- Caffeine, coffee, and appetite control: a review.ReviewInternational journal of food sciences and nutrition · 2017Schubert MM, Irwin C, Seay RF et al.DOI: 10.1080/09637486.2017.1320537
- Caffeine's mechanisms of action and its cosmetic use.ReviewSkin pharmacology and physiology · 2013Herman A, Herman APDOI: 10.1159/000343174
- Coffee and mental disorders: How caffeine affects anxiety and depression.ReviewProgress in brain research · 2024Meamar M, Raise-Abdullahi P, Rashidy-Pour A et al.DOI: 10.1016/bs.pbr.2024.06.015
- Caffeine and Exercise: What Next?ReviewSports medicine (Auckland, N.Z.) · 2019Pickering C, Grgic JDOI: 10.1007/s40279-019-01101-0
- Impacts of Caffeine during Pregnancy.ReviewTrends in endocrinology and metabolism: TEM · 2020Qian J, Chen Q, Ward SM et al.DOI: 10.1016/j.tem.2019.11.004
via PubMed
~62 min read
Encyclopedic overview
69 sectionsContents
- Uses
- Medical
- Enhancing performance
- Cognitive performance
- Physical performance
- Specific populations
- Adults
- Children
- Adolescents
- Pregnancy and breastfeeding
- Adverse effects{{anchor|Side_effects}}
- Physiological
- Psychological
- Reinforcement disorders
- Addiction
- Dependence and withdrawal
- Risk of other diseases
- Energy crash
- Overdose
- Energy drinks
- Severe intoxication
- Lethal dose
- Interactions
- Alcohol
- Smoking
- Birth control
- Medications
- Pharmacology
- Pharmacodynamics
- Receptor and ion channel targets
- Effects on striatal dopamine
- Enzyme targets
- Pharmacokinetics
- Chemistry
- See also
- Synthesis
- Decaffeination
- Detection in body fluids
- Analogs
- Precipitation of tannins
- Commercial sources
- Natural occurrence
- Products
- Beverages
- Coffee
- Tea
- Soft drinks and energy drinks
- Other beverages
- Cacao solids
- Chocolate
- Tablets
- Other oral products
- Inhalants
- Combinations with other drugs
- History
- Discovery and spread of use
- Chemical identification, isolation, and synthesis
- Historic regulations
- Society and culture
- Regulations
- United States
- Consumption
- Religions
- Other organisms
- Research
- See also
- References
- Bibliography
- External links
Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class and is the most commonly consumed psychoactive substance globally. It is mainly used for its eugeroic (wakefulness promoting), ergogenic (physical performance-enhancing), or nootropic (cognitive-enhancing) properties; it is also used recreationally or in social settings. Caffeine acts by blocking the binding of adenosine at a number of adenosine receptor types, inhibiting the centrally depressant effects of adenosine and enhancing the release of acetylcholine. Caffeine has a three-dimensional structure similar to that of adenosine, which allows it to bind and block its receptors. Caffeine also increases cyclic AMP levels through nonselective inhibition of phosphodiesterase, increases calcium release from intracellular stores, and antagonizes GABA receptors, although these mechanisms typically occur at concentrations beyond usual human consumption.
Caffeine is a bitter, white crystalline purine, a methylxanthine alkaloid, and is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, fruits, nuts, or leaves of a number of plants native to Africa, East Asia, and South America and helps to protect them against herbivores and from competition by preventing the germination of nearby seeds, as well as encouraging consumption by select animals such as honey bees. The most common sources of caffeine for human consumption are the tea leaves of the Camellia sinensis plant and the coffee bean, the seed of the Coffea plant. Some people drink beverages containing caffeine to relieve or prevent drowsiness and to improve cognitive performance. To make these drinks, caffeine is extracted by steeping the plant product in water, a process called infusion. Caffeine-containing drinks, such as tea, coffee, and cola, are consumed globally in high volumes. In 2020, almost 10 million tonnes of coffee beans were consumed globally. Caffeine is the world's most widely consumed psychoactive drug. Unlike most other psychoactive substances, caffeine remains largely unregulated and legal in nearly all parts of the world. Caffeine is seen as socially acceptable in most cultures and is encouraged in some.
Excerpted from Wikipedia’s “caffeine” article, available under the CC BY-SA 4.0 licence.
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