{"ATC Code":"N06BC01","Abbreviation":"","Aliases":["Guaranine","1,3,7-Trimethylxanthine","Methyltheobromine","Theine","Thein","Cafeina","Koffein","Mateina","Alert-pep","Caffein"],"Biological Half-Life":"In an average-sized adult or child above the age of 9, the half-life of caffeine is approximately 5 hours. Various characteristics and conditions can alter caffeine half-life.  It can be reduced by up to 50% in smokers. Pregnant women show an increased half-life of 15 hours or higher, especially in the third trimester. The half-life in newborns is prolonged to about 8 hours at full-term and 100 hours in premature infants, likely due to reduced ability to metabolize it. Liver disease or drugs that inhibit CYP1A2 can increase caffeine half-life.","Boiling Point":"352 °","CAS":"58-08-2","ChEBI":"CHEBI:27732","ChEMBL":"CHEMBL113","ChemicalClasses":["xanthine"],"Chirality":"achiral","Classes":null,"Color/Form":"White, prismatic crystals","Decomposition":"When heated to decomposition, it emits toxic fumes of /nitrogen oxides/.","Density":"1.23 at 64 °F (NTP, 1992) - Denser than water; will sink g/cm\u003csup\u003e3\u003c/sup\u003e","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Central Nervous System Stimulants; Phosphodiesterase Inhibitors; Purinergic P1 Receptor Antagonists; Xanthines","Drug Indication":"Caffeine is indicated for the short term treatment of apnea of prematurity in infants and off label for the prevention and treatment of bronchopulmonary dysplasia caused by premature birth. In addition, it is indicated in combination with sodium benzoate to treat respiratory depression resulting from an overdose with CNS depressant drugs. Caffeine has a broad range of over the counter uses, and is found in energy supplements, athletic enhancement products, pain relief products, as well as cosmetic products.","Drug Warnings":"Because it has been suggested that caffeine may promote gastric ulceration, the drug should be used cautiously in patients with a history of peptic ulcer. Because of its suspected arrhythmogenic potential, it is generally recommended that caffeine be avoided in patients with symptomatic cardiac arrhythmias and/or palpitations and during the first several days to weeks after an acute myocardial infarction","DrugClasses":["stimulant","depressant"],"DurationOfAction":"3 – 4 hours\u003ca href='#cite_note-4'\u003e\u003csup\u003e[4]\u003c/sup\u003e\u003c/a\u003e","EINECS":"200-362-1","EliminationHalfLife":"Adults: 3 – 7\u0026nbsp;hours\u003ca href='#cite_note-3'\u003e\u003csup\u003e[3]\u003c/sup\u003e\u003c/a\u003eInfants (full term): 8\u0026nbsp;hoursInfants (premature): 100\u0026nbsp;hours","Erowid Experience Reports":[{"Author":"mcr","Id":"101045","Title":"A Strong Mix"},{"Author":"TDurden","Id":"104808","Title":"Monster Energy Hangover"},{"Author":"016TTU","Id":"106537","Title":"Turnt Da Fuk Up"},{"Author":"Brewman","Id":"10656","Title":"Snorting Caffeine"},{"Author":"Cafag","Id":"107094","Title":"Not Fun and Burned"},{"Author":"AndrewR","Id":"10931","Title":"Caffeine Sweats"},{"Author":"Scorpio","Id":"11019","Title":"Hellish Nightmare"},{"Author":"Vep","Id":"110190","Title":"A Small Pinch in a Meth Pipe"},{"Author":"Habibi","Id":"110613","Title":"Maximizing the Day's Potential"},{"Author":"Jitters","Id":"11206","Title":"Definitely Not a Miracle Cure"},{"Author":"Blue Zinnia","Id":"112169","Title":"The Night It Wasn't My Friend"},{"Author":"Kitten","Id":"11319","Title":"Stung by Yellow Jackets"},{"Author":"Elvira","Id":"114171","Title":"Surprise Result"},{"Author":"Andro","Id":"11601","Title":"I Swallowed Them All"},{"Author":"imlonly","Id":"115950","Title":"Not Worth Snorting"},{"Author":"Swede","Id":"11640","Title":"Something Else to Cheer Me Up"},{"Author":"Big Mike","Id":"1294","Title":"Really Bad Day At School"},{"Author":"anonfoxer","Id":"116868","Title":"Liquid Personality"},{"Author":"Ghost","Id":"1196","Title":"Can Caffeine Really Do This?"},{"Author":"ECGirlie","Id":"1293","Title":"Never Again"},{"Author":"Tony Totosh","Id":"11711","Title":"Ruined My New Year's"},{"Author":"Ani","Id":"12941","Title":"Physically Sick \u0026 Panic Attack"},{"Author":"Goddess","Id":"1309","Title":"I have shit for brains"},{"Author":"Derek Qai","Id":"1343","Title":"The Performance"},{"Author":"anonymous","Id":"14799","Title":"Wild Heart"},{"Author":"Stars","Id":"1428","Title":"Panic Attack and Palpitating Heart"}],"Esters":["benzoate"],"European Community (EC) Number":"200-362-1","FDA Pharmacological Classification":"3G6A5W338E","FullSalts":["Caffeine citrate","Caffeine salicylate","Caffeine monohydrate"],"HMDB ID":"HMDB0001847","HeavyAtomCount":14,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Central Nervous System Stimulants; Phosphodiesterase Inhibitors; Purinergic P1 Receptor Antagonists; Xanthines","IUPACName":"1,3,7-trimethylpurine-2,6-dione","Impurities":["isocaffeine","theobromine","paraxanthine","caffeidine","6-amino-5-formamido-1,3-dimethyluracil","theophylline anhydrous"],"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","MeSH Pharmacological Classification":"A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here. (See all compounds classified as Central Nervous System Stimulants.)","Melting Point":"460 °","MolecularFormula":"C\u003csub\u003e8\u003c/sub\u003eH\u003csub\u003e10\u003c/sub\u003eN\u003csub\u003e4\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"194.19 g/mol","Odor":"Odorless","Pharmacodynamics":"Caffeine stimulates the central nervous system (CNS), heightening alertness, and sometimes causing restlessness and agitation. It relaxes smooth muscle, stimulates the contraction of cardiac muscle, and enhances athletic performance. Caffeine promotes gastric acid secretion and increases gastrointestinal motility. It is often combined in products with analgesics and ergot alkaloids, relieving the symptoms of migraine and other types of headaches. Finally, caffeine acts as a mild diuretic.","Physical Description":"Caffeine appears as odorless white powder or white glistening needles, usually melted together. Bitter taste. Solutions in water are neutral to litmus. Odorless. (NTP, 1992)","PrevSalts":["citrate","salicylate","monohydrate"],"PubChemId":2519,"Record Description":["Caffeine appears as odorless white powder or white glistening needles, usually melted together. Bitter taste. Solutions in water are neutral to litmus. Odorless. (NTP, 1992)","Caffeine is 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. It has a role as a central nervous system stimulant, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an adenosine receptor antagonist, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, a ryanodine receptor agonist, a fungal metabolite, an adenosine A2A receptor antagonist, a psychotropic drug, a diuretic, a food additive, an adjuvant, a plant metabolite, an environmental contaminant, a xenobiotic, a human blood serum metabolite, a mouse metabolite, a geroprotector and a mutagen. It is a purine alkaloid and a trimethylxanthine.","Caffeine is a drug of the methylxanthine class used for a variety of purposes, including certain respiratory conditions of the premature newborn, pain relief, and to combat drowsiness. Caffeine is similar in chemical structure to [Theophylline] and [Theobromine]. It can be sourced from coffee beans, but also occurs naturally in various teas and cacao beans, which are different than coffee beans. Caffeine is also used in a variety of cosmetic products and can be administered topically, orally, by inhalation, or by injection.  The caffeine citrate injection, used for apnea of the premature newborn, was initially approved by the FDA in 1999. According to an article from 2017, more than 15 million babies are born prematurely worldwide. This correlates to about 1 in 10 births. Premature birth can lead to apnea and bronchopulmonary dysplasia, a condition that interferes with lung development and may eventually cause asthma or early onset emphysema in those born prematurely. Caffeine is beneficial in preventing and treating apnea and bronchopulmonary dysplasia in newborns, improving the quality of life of premature infants.","Caffeine is a Central Nervous System Stimulant and Methylxanthine. The physiologic effect of caffeine is by means of Central Nervous System Stimulation.","Caffeine is xanthine alkaloid that occurs naturally in seeds, leaves and fruit of several plants and trees that acts as a natural pesticide. Caffeine is a major component of coffee, tea and chocolate and in humans acts as a central nervous system (CNS) stimulant. Consumption of caffeine, even in high doses, has not been associated with elevations in serum enzyme elevations or instances of clinically apparent liver injury.","Caffeine has been reported in Camellia sinensis, Claviceps sorghicola, and other organisms with data available.","Caffeine is a methylxanthine alkaloid found in the seeds, nuts, or leaves of a number of plants native to South America and East Asia that is structurally related to adenosine and acts primarily as an adenosine receptor antagonist with psychotropic and anti-inflammatory activities. Upon ingestion, caffeine binds to adenosine receptors in the central nervous system (CNS), which inhibits adenosine binding. This inhibits the adenosine-mediated downregulation of CNS activity; thus, stimulating the activity of the medullary, vagal, vasomotor, and respiratory centers in the brain. This agent also promotes neurotransmitter release that further stimulates the CNS. The anti-inflammatory effects of caffeine are due the nonselective competitive inhibition of phosphodiesterases (PDEs). Inhibition of PDEs raises the intracellular concentration of cyclic AMP (cAMP), activates protein kinase A, and inhibits leukotriene synthesis, which leads to reduced inflammation and innate immunity.","CAFFEINE is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1948 and has 4 approved and 59 investigational indications.","Caffeine is the most widely consumed psychostimulant drug in the world that mostly is consumed in the form of coffee. Whether caffeine and/or coffee consumption contribute to the development of cardiovascular disease (CVD), the single leading cause of death in the US, is unclear. The literature indicates a strong relationship between boiled, unfiltered coffee consumption and elevated cholesterol levels; however, there is a critical gap in the literature regarding the effects of coffee or caffeine consumption on fibrinogen or CRP, which is an independent predictor of CVD risk. Available studies are limited by small samples sizes, inclusion of only men (or few women) and unrepresented age or ethnic groups. There is a critical need for controlled laboratory and epidemiological studies that include fibrinogen and CRP markers of CVD risk before conclusions can be drawn regarding the health effects of caffeine and/or coffee in a normal, healthy population of men and women. (A11723). The relationship between caffeine consumption and various illnesses such as cardiovascular disease and cancer remains equivocal. Prudence might dictate that pregnant women and chronically ill individuals exercise restraint in their use of caffeine, although research suggests relatively low or nonexistent levels of risk associated with moderate caffeine consumption. (A7827). There is extensive evidence that caffeine at dietary doses increases blood pressure (BP). However, concern that the drug may contribute to cardiovascular disease appears to have been dampened by (1) the belief that habitual use leads to the development of tolerance, and (2) confusion regarding relevant epidemiologic findings. When considered comprehensively, findings from experimental and epidemiologic studies converge to show that BP remains reactive to the pressor effects of caffeine in the diet. Overall, the impact of dietary caffeine on population BP levels is likely to be modest, probably in the region of 4/2 mm Hg. At these levels, however, population studies of BP indicate that caffeine use could account for premature deaths in the region of 14% for coronary heart disease and 20% for stroke. (A7828). Caffeine is a purine alkaloid that occurs naturally in coffee beans. At intake levels associated with coffee consumption, caffeine appears to exert most of its biological effects through the antagonism of the A1 and A2A subtypes of the adenosine receptor. Adenosine is an endogenous neuromodulator with mostly inhibitory effects, and adenosine antagonism by caffeine results in effects that are generally stimulatory. Some physiological effects associated with caffeine administration include central nervous system stimulation, acute elevation of blood pressure, increased metabolic rate, and diuresis. Caffeine concentrations in coffee beverages can be quite variable. A standard cup of coffee is often assumed to provide 100 mg of caffeine, but a recent analysis of 14 different specialty coffees purchased at coffee shops in the US found that the amount of caffeine in 8 oz (=240 ml) of brewed coffee ranged from 72 to 130 mg.Caffeine in espresso coffees ranged from 58 to 76 mg in a single shot. (A7829). Caffeine is a member of the methylxanthine family of drugs, and is the most widely consumed behaviourally active substance in the western world. A number of in vitro and in vivo studies have demonstrated that caffeine modulates both innate and adaptive immune responses. For instance studies indicate that caffeine and its major metabolite paraxanthine suppress neutrophil and monocyte chemotaxis, and also suppress production of the pro-inflammatory cytokine tumor necrosis factor (TNF) alpha from human blood. Caffeine has also been reported to suppress human lymphocyte function as indicated by reduced T-cell proliferation and impaired production of Th1 (interleukin [IL]-2 and interferon [IFN]-gamma), Th2 (IL-4, IL-5) and Th3 (IL-10) cytokines. Studies also indicate that caffeine suppresses antibody production. The evidence suggests that at least some of the immunomodulatory actions of caffeine are mediated via inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE), and consequential increase in intracellular cAMP concentrations. Overall, these studies indicate that caffeine, like other members of the methylxanthine family, is largely anti-inflammatory in nature, and based on the pharmacokinetics of caffeine, many of its immunomodulatory effects occur at concentrations that are relevant to normal human consumption. (A7830).","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.","See also: Caffeine Citrate (has salt form); Acetaminophen; Butalbital; Caffeine (component of); Aspirin; caffeine; orphenadrine citrate (component of) ... View More ...","Caffeine is 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. It has a role as a central nervous system stimulant, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an adenosine receptor antagonist, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, a ryanodine receptor agonist, a fungal metabolite, an adenosine A2A receptor antagonist, a psychotropic drug, a diuretic, a food additive, an adjuvant, a plant metabolite, an environmental contaminant, a xenobiotic, a human blood serum metabolite, a mouse metabolite, a geroprotector and a mutagen. It is a purine alkaloid and a trimethylxanthine.","LiverTox|CNS|Stimulant|Xanthine"],"RefCount":5,"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Caffeine","Name":"Caffeine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q60235","Name":"Caffeine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00201","Name":"Caffeine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/2519","Name":"Caffeine","Sub":false}]},{"Name":"Sciencemadness","Urls":[{"Link":"https://www.sciencemadness.org/smwiki/index.php/Caffeine","Name":"Caffeine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL113","Name":"Caffeine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27732","Name":"Caffeine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=58-08-2","Name":"Caffeine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0001847","Name":"Caffeine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07481","Name":"Caffeine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/3G6A5W338E","Name":"Caffeine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID0020232","Name":"Caffeine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 2519, Caffeine. Accessed June 29, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/2519\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/2519\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Caffeine. UNII: 3G6A5W338E. Global Substance Registration System. Accessed June 29, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/3G6A5W338E\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/3G6A5W338E\u003c/a\u003e","Caffeine. University of Alberta. September 16, 2013. Accessed June 29, 2025. \u003ca href=http://www.drugbank.ca/drugs/DB00201#pharmacology\u003ehttp://www.drugbank.ca/drugs/DB00201#pharmacology\u003c/a\u003e","Poleszak E, Szopa A, Wyska E, Kukuła-Koch W, Serefko A, Wośko S, Bogatko K, Wróbel A, Wlaź P. Caffeine augments the antidepressant-like activity of mianserin and agomelatine in forced swim and tail suspension tests in mice. Pharmacological Reports. February 1, 2016; 68(1):56–61."],"Reported Fatal Dose":"In adults, iv doses of 57 mg/kg and oral doses of 18-50 g have been fatal.","SMILES":"CN1C=NC2=C1C(=O)N(C(=O)N2C)C","Salts":["citrate","salicylate","monohydrate"],"SaltsAcidCount":[1,1,1],"SaltsAmineCount":[1,1,1],"SaltsUNII":["U26EO4675Q","U7R78VQQ6O","9T65I06326"],"Scheduling":[{"gov":"Australia","ref":[],"schedule":"Unscheduled substance"},{"gov":"Brazil","ref":[],"schedule":"Unscheduled substance"},{"gov":"Canada","ref":[],"schedule":"Unscheduled substance"},{"gov":"Germany","ref":[],"schedule":"Unscheduled substance"},{"gov":"New Zealand","ref":[],"schedule":"Unscheduled substance"},{"gov":"United Kingdom","ref":[],"schedule":"GSL substance"},{"gov":"United States","ref":[],"schedule":"Unscheduled substance"},{"gov":"United Nations","ref":[],"schedule":"Unscheduled substance"}],"ScienceMadness":"Caffeine","Solubility":"10 to 50 mg/mL at 73 °F (NTP, 1992)","StoreUNII":["3G6A5W338E"],"StructureBase64":"<svg xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" height="64.951mm" version="1.2" viewBox="0 0 66.951 64.951" width="66.951mm">
      
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