CHEBI:27732 - caffeine

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ChEBI Name caffeine
ChEBI ID CHEBI:27732
Definition A trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3295, CHEBI:41472, CHEBI:22982
Supplier Information eMolecules:27517656, eMolecules:493944, ZINC000000001084
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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. Caffeine acts by blocking 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 best-known source of caffeine is the coffee bean, the seed of the Coffea plant. People may 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 coffee, tea, 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 also an outlier as its use is seen as socially acceptable in most cultures with it even being encouraged. Caffeine has both positive and negative health effects. It can treat and prevent the premature infant breathing disorders bronchopulmonary dysplasia of prematurity and apnea of prematurity. Caffeine citrate is on the WHO Model List of Essential Medicines. It may confer a modest protective effect against some diseases, including Parkinson's disease. Some people experience sleep disruption or anxiety if they consume caffeine, but others show little disturbance. Evidence of a risk during pregnancy is equivocal; some authorities recommend that pregnant women limit caffeine to the equivalent of two cups of coffee per day or less. Caffeine can produce a mild form of drug dependence – associated with withdrawal symptoms such as sleepiness, headache, and irritability – when an individual stops using caffeine after repeated daily intake. Tolerance to the autonomic effects of increased blood pressure and heart rate, and increased urine output, develops with chronic use (i.e., these symptoms become less pronounced or do not occur following consistent use). Caffeine is classified by the U.S. Food and Drug Administration (FDA) as generally recognized as safe. Toxic doses, over 10 grams per day for an adult, are much higher than the typical dose of under 500 milligrams per day. The European Food Safety Authority reported that up to 400 mg of caffeine per day (around 5.7 mg/kg of body mass per day) does not raise safety concerns for non-pregnant adults, while intakes up to 200 mg per day for pregnant and lactating women do not raise safety concerns for the fetus or the breast-fed infants. A cup of coffee contains 80–175 mg of caffeine, depending on what "bean" (seed) is used, how it is roasted, and how it is prepared (e.g., drip, percolation, or espresso). Thus it requires roughly 50–100 ordinary cups of coffee to reach the toxic dose. However, pure powdered caffeine, which is available as a dietary supplement, can be lethal in tablespoon-sized amounts.
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Formula C8H10N4O2
Net Charge 0
Average Mass 194.19076
Monoisotopic Mass 194.08038
InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChIKey RYYVLZVUVIJVGH-UHFFFAOYSA-N
SMILES Cn1cnc2n(C)c(=O)n(C)c(=O)c12
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Theobroma cacao (NCBI:txid3641) See: DOI
Camellia sinensis (NCBI:txid4442) See: PubMed
Claviceps sorghicola (NCBI:txid83213) See: DOI
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): EC 3.1.4.* (phosphoric diester hydrolase) inhibitor
An EC 3.1.* (ester hydrolase) inhibitor that interferes with the action of a phosphoric diester hydrolase (EC 3.1.4.*).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine.
ryanodine receptor agonist
A ryanodine receptor modulator which activates the receptor. Ryanodine receptors (RyRs) act as selective ion channels, modulating the release of calcium. Activating the receptors causes the release of calcium, so depleting internal calcium and ultimately preventing further muscle contraction.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
adenosine A2A receptor antagonist
An antagonist at the A2A receptor.
food additive
Any substance which is added to food to preserve or enhance its flavour and/or appearance.
adenosine receptor antagonist
An antagonist at any adenosine receptor.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
mutagen
An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
diuretic
An agent that promotes the excretion of urine through its effects on kidney function.
food additive
Any substance which is added to food to preserve or enhance its flavour and/or appearance.
adjuvant
Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself.
central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing caffeine (CHEBI:27732) has role adenosine A2A receptor antagonist (CHEBI:53121)
caffeine (CHEBI:27732) has role adenosine receptor antagonist (CHEBI:71232)
caffeine (CHEBI:27732) has role adjuvant (CHEBI:60809)
caffeine (CHEBI:27732) has role central nervous system stimulant (CHEBI:35337)
caffeine (CHEBI:27732) has role diuretic (CHEBI:35498)
caffeine (CHEBI:27732) has role EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor (CHEBI:50925)
caffeine (CHEBI:27732) has role EC 3.1.4.* (phosphoric diester hydrolase) inhibitor (CHEBI:50218)
caffeine (CHEBI:27732) has role environmental contaminant (CHEBI:78298)
caffeine (CHEBI:27732) has role food additive (CHEBI:64047)
caffeine (CHEBI:27732) has role fungal metabolite (CHEBI:76946)
caffeine (CHEBI:27732) has role geroprotector (CHEBI:176497)
caffeine (CHEBI:27732) has role human blood serum metabolite (CHEBI:85234)
caffeine (CHEBI:27732) has role mouse metabolite (CHEBI:75771)
caffeine (CHEBI:27732) has role mutagen (CHEBI:25435)
caffeine (CHEBI:27732) has role plant metabolite (CHEBI:76924)
caffeine (CHEBI:27732) has role psychotropic drug (CHEBI:35471)
caffeine (CHEBI:27732) has role ryanodine receptor agonist (CHEBI:67114)
caffeine (CHEBI:27732) has role xenobiotic (CHEBI:35703)
caffeine (CHEBI:27732) is a purine alkaloid (CHEBI:26385)
caffeine (CHEBI:27732) is a trimethylxanthine (CHEBI:27134)
Incoming 8-(3-chlorostyryl)caffeine (CHEBI:53115) has functional parent caffeine (CHEBI:27732)
caffeine monohydrate (CHEBI:31332) has part caffeine (CHEBI:27732)
sodium caffeine benzoate (CHEBI:32140) has part caffeine (CHEBI:27732)
IUPAC Name
1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione
Synonyms Sources
1,3,7-trimethyl-2,6-dioxopurine ChemIDplus
1,3,7-trimethylpurine-2,6-dione IUPHAR
1,3,7-Trimethylxanthine KEGG COMPOUND
1,3,7-trimethylxanthine NIST Chemistry WebBook
1-methyltheobromine ChemIDplus
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion NIST Chemistry WebBook
7-methyltheophylline NIST Chemistry WebBook
anhydrous caffeine KEGG DRUG
cafeína ChemIDplus
caféine ChEBI
CAFFEINE PDBeChem
Caffeine KEGG COMPOUND
caffeine UniProt
Coffein ChemIDplus
guaranine IUPHAR
Koffein ChemIDplus
mateína ChemIDplus
methyltheobromine IUPHAR
teína ChEBI
Thein ChemIDplus
theine NIST Chemistry WebBook
Manual Xrefs Databases
1-3-7-TRIMETHYLXANTHINE MetaCyc
463 DrugCentral
C00001492 KNApSAcK
C07481 KEGG COMPOUND
Caffeine Wikipedia
CFF PDBeChem
D00528 KEGG DRUG
DB00201 DrugBank
HMDB0001847 HMDB
LSM-2026 LINCS
View more database links
Registry Numbers Types Sources
103040 Gmelin Registry Number Gmelin
17705 Reaxys Registry Number Reaxys
58-08-2 CAS Registry Number KEGG COMPOUND
58-08-2 CAS Registry Number NIST Chemistry WebBook
58-08-2 CAS Registry Number ChemIDplus
Citations
Rallis C, Codlin S, Bähler J (2013)
TORC1 signaling inhibition by rapamycin and caffeine affect lifespan, global gene expression, and cell proliferation of fission yeast.
Aging cell 12, 563-573 [PubMed:23551936]
[show Abstract]
Romano GH, Harari Y, Yehuda T, Podhorzer A, Rubinstein L, Shamir R, Gottlieb A, Silberberg Y, Pe'er D, Ruppin E, Sharan R, Kupiec M (2013)
Environmental stresses disrupt telomere length homeostasis.
PLoS genetics 9, e1003721 [PubMed:24039592]
[show Abstract]
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]
Lublin A, Isoda F, Patel H, Yen K, Nguyen L, Hajje D, Schwartz M, Mobbs C (2011)
FDA-approved drugs that protect mammalian neurons from glucose toxicity slow aging dependent on cbp and protect against proteotoxicity.
PloS one 6, e27762 [PubMed:22114686]
[show Abstract]
Chen GQ, Chen YY, Wang XS, Wu SZ, Yang HM, Xu HQ, He JC, Wang XT, Chen JF, Zheng RY (2010)
Chronic caffeine treatment attenuates experimental autoimmune encephalomyelitis induced by guinea pig spinal cord homogenates in Wistar rats.
Brain research 1309, 116-125 [PubMed:19879252]
[show Abstract]
Chen X, Ghribi O, Geiger JD (2010)
Caffeine protects against disruptions of the blood-brain barrier in animal models of Alzheimer's and Parkinson's diseases.
Journal of Alzheimer's disease : JAD 20 Suppl 1, S127-41 [PubMed:20164568]
[show Abstract]
Goldstein E, Jacobs PL, Whitehurst M, Penhollow T, Antonio J (2010)
Caffeine enhances upper body strength in resistance-trained women.
Journal of the International Society of Sports Nutrition 7, 18 [PubMed:20470411]
[show Abstract]
Kasture S, Barhate S, Mohan M, Ballero M, Sanna C, Maxia A (2009)
Caffeine withdrawal retains anticataleptic activity but Withania somnifera withdrawal potentiates haloperidol-induced catalepsy in mice.
Natural product research 23, 724-728 [PubMed:19418355]
[show Abstract]
Chavez-Valdez R, Wills-Karp M, Ahlawat R, Cristofalo EA, Nathan A, Gauda EB (2009)
Caffeine modulates TNF-alpha production by cord blood monocytes: the role of adenosine receptors.
Pediatric research 65, 203-208 [PubMed:19047957]
[show Abstract]
Hume JR, McAllister CE, Wilson SM (2009)
Caffeine inhibits InsP3 responses and capacitative calcium entry in canine pulmonary arterial smooth muscle cells.
Vascular pharmacology 50, 89-97 [PubMed:19084078]
[show Abstract]
Graham TE, Battram DS, Dela F, El-Sohemy A, Thong FS (2008)
Does caffeine alter muscle carbohydrate and fat metabolism during exercise?
Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme 33, 1311-1318 [PubMed:19088793]
[show Abstract]
Moore MT, Greenway SL, Farris JL, Guerra B (2008)
Assessing caffeine as an emerging environmental concern using conventional approaches.
Archives of environmental contamination and toxicology 54, 31-35 [PubMed:17957400]
[show Abstract]
Díaz-Reval MI, Galván-Orozco R, López-Muñoz FJ, Carrillo-Munguía N (2008)
[Synergism of caffeine on antinociceptive effects of metamizole].
Cirugia y cirujanos 76, 241-246 [PubMed:18647558]
[show Abstract]
Shapiro RE (2008)
Caffeine and headaches.
Current pain and headache reports 12, 311-315 [PubMed:18625110]
[show Abstract]
da Silva RS, Richetti SK, da Silveira VG, Battastini AM, Bogo MR, Lara DR, Bonan CD (2008)
Maternal caffeine intake affects acetylcholinesterase in hippocampus of neonate rats.
International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 26, 339-343 [PubMed:18258404]
[show Abstract]
Chin JM, Merves ML, Goldberger BA, Sampson-Cone A, Cone EJ (2008)
Caffeine content of brewed teas.
Journal of analytical toxicology 32, 702-704 [PubMed:19007524]
[show Abstract]
Yang R, Wang J, Chen Y, Sun Z, Wang R, Dai Y (2008)
Effect of caffeine on erectile function via up-regulating cavernous cyclic guanosine monophosphate in diabetic rats.
Journal of andrology 29, 586-591 [PubMed:18421070]
[show Abstract]
Ravi D, Muniyappa H, Das KC (2008)
Caffeine inhibits UV-mediated NF-kappaB activation in A2058 melanoma cells: an ATM-PKCdelta-p38 MAPK-dependent mechanism.
Molecular and cellular biochemistry 308, 193-200 [PubMed:17932622]
[show Abstract]
Wanke V, Cameroni E, Uotila A, Piccolis M, Urban J, Loewith R, De Virgilio C (2008)
Caffeine extends yeast lifespan by targeting TORC1.
Molecular microbiology 69, 277-285 [PubMed:18513215]
[show Abstract]
Ashihara H, Sano H, Crozier A (2008)
Caffeine and related purine alkaloids: biosynthesis, catabolism, function and genetic engineering.
Phytochemistry 69, 841-856 [PubMed:18068204]
[show Abstract]
Pardo Lozano R, Alvarez García Y, Barral Tafalla D, Farré Albaladejo M (2007)
[Caffeine: a nutrient, a drug or a drug of abuse].
Adicciones 19, 225-238 [PubMed:17724925]
[show Abstract]
Bode AM, Dong Z (2007)
The enigmatic effects of caffeine in cell cycle and cancer.
Cancer letters 247, 26-39 [PubMed:16709440]
[show Abstract]
Judd K, Shugert E, Vélez SJ (2007)
Depressing effects of caffeine at crayfish neuromuscular synapses I. Dosage response and Ca++ gradient effects.
Cellular and molecular neurobiology 27, 367-380 [PubMed:17387608]
[show Abstract]
Shapiro RE (2007)
Caffeine and headaches.
Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology 28 Suppl 2, S179-83 [PubMed:17508167]
[show Abstract]
McCusker RR, Fuehrlein B, Goldberger BA, Gold MS, Cone EJ (2006)
Caffeine content of decaffeinated coffee.
Journal of analytical toxicology 30, 611-613 [PubMed:17132260]
[show Abstract]
Conde SV, Obeso A, Vicario I, Rigual R, Rocher A, Gonzalez C (2006)
Caffeine inhibition of rat carotid body chemoreceptors is mediated by A2A and A2B adenosine receptors.
Journal of neurochemistry 98, 616-628 [PubMed:16805851]
[show Abstract]
Vavra-Hadziahmetović N, Hadziahmetović Z (2006)
[The effects of physical therapy in prevention of deep vein thrombosis (DVT) in the "syndrome of economy class"].
Medicinski arhiv 60, 115-116 [PubMed:16528931]
[show Abstract]
Wu WP, Hao JX, Fredholm BB, Wiesenfeld-Hallin Z, Xu XJ (2006)
Effect of acute and chronic administration of caffeine on pain-like behaviors in rats with partial sciatic nerve injury.
Neuroscience letters 402, 164-166 [PubMed:16644114]
[show Abstract]
Al-Wadei HA, Takahashi T, Schuller HM (2006)
Caffeine stimulates the proliferation of human lung adenocarcinoma cells and small airway epithelial cells via activation of PKA, CREB and ERK1/2.
Oncology reports 15, 431-435 [PubMed:16391865]
[show Abstract]
Rodrigues IM, Klein LC (2006)
Boiled or filtered coffee? Effects of coffee and caffeine on cholesterol, fibrinogen and C-reactive protein.
Toxicological reviews 25, 55-69 [PubMed:16856769]
[show Abstract]
Varani K, Portaluppi F, Gessi S, Merighi S, Vincenzi F, Cattabriga E, Dalpiaz A, Bortolotti F, Belardinelli L, Borea PA (2005)
Caffeine intake induces an alteration in human neutrophil A2A adenosine receptors.
Cellular and molecular life sciences : CMLS 62, 2350-2358 [PubMed:16143823]
[show Abstract]
Daniel R, Marusich E, Argyris E, Zhao RY, Skalka AM, Pomerantz RJ (2005)
Caffeine inhibits human immunodeficiency virus type 1 transduction of nondividing cells.
Journal of virology 79, 2058-2065 [PubMed:15681408]
[show Abstract]
Prediger RD, Batista LC, Takahashi RN (2005)
Caffeine reverses age-related deficits in olfactory discrimination and social recognition memory in rats. Involvement of adenosine A1 and A2A receptors.
Neurobiology of aging 26, 957-964 [PubMed:15718055]
[show Abstract]
Nunnari G, Argyris E, Fang J, Mehlman KE, Pomerantz RJ, Daniel R (2005)
Inhibition of HIV-1 replication by caffeine and caffeine-related methylxanthines.
Virology 335, 177-184 [PubMed:15840517]
[show Abstract]
Chiarella P, Puglisi R, Sorrentino V, Boitani C, Stefanini M (2004)
Ryanodine receptors are expressed and functionally active in mouse spermatogenic cells and their inhibition interferes with spermatogonial differentiation.
Journal of cell science 117, 4127-4134 [PubMed:15280431]
[show Abstract]
Landolt HP, Rétey JV, Tönz K, Gottselig JM, Khatami R, Buckelmüller I, Achermann P (2004)
Caffeine attenuates waking and sleep electroencephalographic markers of sleep homeostasis in humans.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 29, 1933-1939 [PubMed:15257305]
[show Abstract]
Waldvogel SR (2003)
Caffeine--a drug with a surprise.
Angewandte Chemie (International ed. in English) 42, 604-605 [PubMed:12574990]
Cherif A, Marrakchi Z, Klouz A, Chaouachi S, Belkahia C, Boukef-Larguèche S (2003)
[Pharmacologic study of monohydrated caffeine in the treatment of apnoea of premature infant].
Archives de pediatrie : organe officiel de la Societe francaise de pediatrie 10, 517-520 [PubMed:12915014]
[show Abstract]
McCusker RR, Goldberger BA, Cone EJ (2003)
Caffeine content of specialty coffees.
Journal of analytical toxicology 27, 520-522 [PubMed:14607010]
[show Abstract]
Murphy JA, Deurveilher S, Semba K (2003)
Stimulant doses of caffeine induce c-FOS activation in orexin/hypocretin-containing neurons in rat.
Neuroscience 121, 269-275 [PubMed:14521986]
[show Abstract]
Al Moutaery K, Al Deeb S, Ahmad Khan H, Tariq M (2003)
Caffeine impairs short-term neurological outcome after concussive head injury in rats.
Neurosurgery 53, 704-11; discussion 711-2 [PubMed:12943586]
[show Abstract]
Keijzers GB, De Galan BE, Tack CJ, Smits P (2002)
Caffeine can decrease insulin sensitivity in humans.
Diabetes care 25, 364-369 [PubMed:11815511]
[show Abstract]
Keogh E, Chaloner N (2002)
The moderating effect of anxiety sensitivity on caffeine-induced hypoalgesia in healthy women.
Psychopharmacology 164, 429-431 [PubMed:12457274]
[show Abstract]
Hoesch RE, Weinreich D, Kao JP (2001)
A novel Ca(2+) influx pathway in mammalian primary sensory neurons is activated by caffeine.
Journal of neurophysiology 86, 190-196 [PubMed:11431501]
[show Abstract]
Donovan JL, DeVane CL (2001)
A primer on caffeine pharmacology and its drug interactions in clinical psychopharmacology.
Psychopharmacology bulletin 35, 30-48 [PubMed:12397877]
[show Abstract]
Christian MS, Brent RL (2001)
Teratogen update: evaluation of the reproductive and developmental risks of caffeine.
Teratology 64, 51-78 [PubMed:11410911]
[show Abstract]
Rayburn AL, Bouma J, Northcott CA (2001)
Comparing the clastogenic potential of atrazine with caffeine using Chinese hamster ovary (CHO) cells.
Toxicology letters 121, 69-78 [PubMed:11312039]
[show Abstract]
Dager SR, Friedman SD (2000)
Brain imaging and the effects of caffeine and nicotine.
Annals of medicine 32, 592-599 [PubMed:11209966]
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Cavalcante JW, Santos PR, Menezes MG, Marques HO, Cavalcante LP, Pacheco WS (2000)
Influence of caffeine on blood pressure and platelet aggregation.
Arquivos brasileiros de cardiologia 75, 97-105 [PubMed:10983026]
[show Abstract]
Esser MJ, Sawynok J (2000)
Caffeine blockade of the thermal antihyperalgesic effect of acute amitriptyline in a rat model of neuropathic pain.
European journal of pharmacology 399, 131-139 [PubMed:10884512]
[show Abstract]
Temple JG, Warm JS, Dember WN, Jones KS, LaGrange CM, Matthews G (2000)
The effects of signal salience and caffeine on performance, workload, and stress in an abbreviated vigilance task.
Human factors 42, 183-194 [PubMed:11022879]
[show Abstract]
Gannon BA (2000)
Theophylline or caffeine: which is best for apnea of prematurity?
Neonatal network : NN 19, 33-36 [PubMed:11949272]
[show Abstract]
Bogo A, Mantle PG (2000)
Caffeine: also a fungal metabolite.
Phytochemistry 54, 937-939 [PubMed:11014293]
[show Abstract]
Tofovic SP, Rominski BR, Bastacky S, Jackso EK, Kost CK (2000)
Caffeine augments proteinuria in puromycin-aminonucleoside nephrotic rats.
Renal failure 22, 159-179 [PubMed:10803761]
[show Abstract]
Bara AI, Barley EA (2000)
Caffeine for asthma.
The Cochrane database of systematic reviewsCD001112 [PubMed:10796597]
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Sinclair CJ, Geiger JD (2000)
Caffeine use in sports. A pharmacological review.
The Journal of sports medicine and physical fitness 40, 71-79 [PubMed:10822912]
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Granados-Soto V, Castañeda-Hernández G (1999)
A review of the pharmacokinetic and pharmacodynamic factors in the potentiation of the antinociceptive effect of nonsteroidal anti-inflammatory drugs by caffeine.
Journal of pharmacological and toxicological methods 42, 67-72 [PubMed:10924888]
[show Abstract]
Dassesse D, Vanderwinden JM, Goldberg I, Vanderhaeghen JJ, Schiffmann SN (1999)
Caffeine-mediated induction of c-fos, zif-268 and arc expression through A1 receptors in the striatum: different interactions with the dopaminergic system.
The European journal of neuroscience 11, 3101-3114 [PubMed:10510174]
[show Abstract]
Okada M, Kiryu K, Kawata Y, Mizuno K, Wada K, Tasaki H, Kaneko S (1997)
Determination of the effects of caffeine and carbamazepine on striatal dopamine release by in vivo microdialysis.
European journal of pharmacology 321, 181-188 [PubMed:9063686]
[show Abstract]
Garrett BE, Griffiths RR (1997)
The role of dopamine in the behavioral effects of caffeine in animals and humans.
Pharmacology, biochemistry, and behavior 57, 533-541 [PubMed:9218278]
[show Abstract]
Ercan-Fang N, Nuttall FQ (1997)
The effect of caffeine and caffeine analogs on rat liver phosphorylase a activity.
The Journal of pharmacology and experimental therapeutics 280, 1312-1318 [PubMed:9067318]
[show Abstract]
Devasagayam TP, Kamat JP, Mohan H, Kesavan PC (1996)
Caffeine as an antioxidant: inhibition of lipid peroxidation induced by reactive oxygen species.
Biochimica et biophysica acta 1282, 63-70 [PubMed:8679661]
[show Abstract]
Tarnopolsky MA (1994)
Caffeine and endurance performance.
Sports medicine (Auckland, N.Z.) 18, 109-125 [PubMed:9132918]
[show Abstract]
Jaw S, Jeffery EH (1993)
Interaction of caffeine with acetaminophen. 1. Correlation of the effect of caffeine on acetaminophen hepatotoxicity and acetaminophen bioactivation following treatment of mice with various cytochrome P450 inducing agents.
Biochemical pharmacology 46, 493-501 [PubMed:8347173]
[show Abstract]
Schiffmann SN, Vanderhaeghen JJ (1993)
Caffeine regulates neurotensin and cholecystokinin messenger RNA expression in the rat striatum.
Neuroscience 54, 681-689 [PubMed:8332255]
[show Abstract]
Howell LL (1993)
Comparative effects of caffeine and selective phosphodiesterase inhibitors on respiration and behavior in rhesus monkeys.
The Journal of pharmacology and experimental therapeutics 266, 894-903 [PubMed:7689104]
[show Abstract]
D'Ambrosio SM, Setlow RB (1980)
Modulation by caffeine of enhanced postreplication repair in mammalian cells treated with N-acetoxy-acetylaminofluorene.
Journal of environmental pathology and toxicology 4, 181-191 [PubMed:7441110]
[show Abstract]
Last Modified
20 September 2021
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag