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a b c Desk reference to the diagnostic criteria from DSM-5. Arlington, VA: American Psychiatric Association. 2013. pp.238–239. ISBN 978-0-89042-556-5. Grosso G, Micek A, Castellano S, Pajak A, Galvano F (January 2016). "Coffee, tea, caffeine and risk of depression: A systematic review and dose-response meta-analysis of observational studies". Molecular Nutrition & Food Research. 60 (1): 223–34. doi: 10.1002/mnfr.201500620. PMID 26518745. Theophylline (4%): Relaxes smooth muscles of the bronchi, and is used to treat asthma. The therapeutic dose of theophylline, however, is many times greater than the levels attained from caffeine metabolism. [46] Food Standards Agency publishes new caffeine advice for pregnant women". Archived from the original on 17 October 2010 . Retrieved 3 August 2009.

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a b "ICD-11 – Mortality and Morbidity Statistics". icd.who.int. Archived from the original on 1 August 2018 . Retrieved 25 November 2019. Some analog substances have been created which mimic caffeine's properties with either function or structure or both. Of the latter group are the xanthines DMPX [210] and 8-chlorotheophylline, which is an ingredient in dramamine. Members of a class of nitrogen substituted xanthines are often proposed as potential alternatives to caffeine. [211] [ unreliable source?] Many other xanthine analogues constituting the adenosine receptor antagonist class have also been elucidated. [212] Schmidt B, Roberts RS, Davis P, Doyle LW, Barrington KJ, Ohlsson A, Solimano A, Tin W (November 2007). "Long-term effects of caffeine therapy for apnea of prematurity". The New England Journal of Medicine. 357 (19): 1893–902. doi: 10.1056/NEJMoa073679. PMID 17989382. S2CID 22983543. Schmidt B (2005). "Methylxanthine therapy for apnea of prematurity: evaluation of treatment benefits and risks at age 5 years in the international Caffeine for Apnea of Prematurity (CAP) trial". Biology of the Neonate. 88 (3): 208–13. doi: 10.1159/000087584. PMID 16210843. S2CID 30123372. a b Qi H, Li S (April 2014). "Dose-response meta-analysis on coffee, tea and caffeine consumption with risk of Parkinson's disease". Geriatrics & Gerontology International. 14 (2): 430–9. doi: 10.1111/ggi.12123. PMID 23879665. S2CID 42527557.Salerno BB, Knights EK (2010). Pharmacology for health professionals (3rded.). Chatswood, N.S.W.: Elsevier Australia. p.433. ISBN 978-0-7295-3929-6. In contrast to the amphetamines, caffeine does not cause euphoria, stereotyped behaviors or psychoses. Gupta V, Lipsitz LA (October 2007). "Orthostatic hypotension in the elderly: diagnosis and treatment". The American Journal of Medicine. 120 (10): 841–7. doi: 10.1016/j.amjmed.2007.02.023. PMID 17904451. The biosynthesis of caffeine is an example of convergent evolution among different species. [202] [203] [204]

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a b c d e f g h i j k l m n o p "Caffeine". DrugBank. University of Alberta. 16 September 2013. Archived from the original on 4 May 2015 . Retrieved 8 August 2014. In 1895, German chemist Hermann Emil Fischer (1852–1919) first synthesized caffeine from its chemical components (i.e. a " total synthesis"), and two years later, he also derived the structural formula of the compound. [267] This was part of the work for which Fischer was awarded the Nobel Prize in 1902. [268] Historic regulations Tea contains more caffeine than coffee by dry weight. A typical serving, however, contains much less, since less of the product is used as compared to an equivalent serving of coffee. Also contributing to caffeine content are growing conditions, processing techniques, and other variables. Thus, teas contain varying amounts of caffeine. [231] Extraction by organic solvents: Certain organic solvents such as ethyl acetate present much less health and environmental hazard than chlorinated and aromatic organic solvents used formerly. Another method is to use triglyceride oils obtained from spent coffee grounds. [207] Desk reference to the diagnostic criteria from DSM-5. 2013. ISBN 978-0-89042-556-5. OCLC 825047464. {{ cite book}}: |work= ignored ( help)

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In 1827, M. Oudry isolated "théine" from tea, [264] but in 1838 it was proved by Mulder [265] and by Carl Jobst [266] that theine was actually the same as caffeine. Gibbons CH, Schmidt P, Biaggioni I, Frazier-Mills C, Freeman R, Isaacson S, Karabin B, Kuritzky L, Lew M, Low P, Mehdirad A, Raj SR, Vernino S, Kaufmann H (August 2017). "The recommendations of a consensus panel for the screening, diagnosis, and treatment of neurogenic orthostatic hypotension and associated supine hypertension". J. Neurol. 264 (8): 1567–1582. doi: 10.1007/s00415-016-8375-x. PMC 5533816. PMID 28050656. a b "Caffeine: Summary of Clinical Use". IUPHAR Guide to Pharmacology. The International Union of Basic and Clinical Pharmacology. Archived from the original on 14 February 2015 . Retrieved 13 February 2015. While caffeine does not directly bind to any dopamine receptors, it influences the binding activity of dopamine at its receptors in the striatum by binding to adenosine receptors that have formed GPCR heteromers with dopamine receptors, specifically the A 1– D 1 receptor heterodimer (this is a receptor complex with 1 adenosine A 1 receptor and 1 dopamine D 1 receptor) and the A 2A– D 2 receptor heterotetramer (this is a receptor complex with 2 adenosine A 2A receptors and 2 dopamine D 2 receptors). [169] [170] [171] [172] The A 2A–D 2 receptor heterotetramer has been identified as a primary pharmacological target of caffeine, primarily because it mediates some of its psychostimulant effects and its pharmacodynamic interactions with dopaminergic psychostimulants. [170] [171] [172]

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Santos C, Costa J, Santos J, Vaz-Carneiro A, Lunet N (2010). "Caffeine intake and dementia: systematic review and meta-analysis". Journal of Alzheimer's Disease. 20 (Suppl 1): S187-204. doi: 10.3233/JAD-2010-091387. PMID 20182026. Caffeine in a dose dependent manner increases alertness in both fatigued and normal individuals. [56] a b c Wright GA, Baker DD, Palmer MJ, Stabler D, Mustard JA, Power EF, Borland AM, Stevenson PC (March 2013). "Caffeine in floral nectar enhances a pollinator's memory of reward". Science. 339 (6124): 1202–4. Bibcode: 2013Sci...339.1202W. doi: 10.1126/science.1228806. PMC 4521368. PMID 23471406. Wang L, Shen X, Wu Y, Zhang D (March 2016). "Coffee and caffeine consumption and depression: A meta-analysis of observational studies". The Australian and New Zealand Journal of Psychiatry. 50 (3): 228–42. doi: 10.1177/0004867415603131. PMID 26339067. S2CID 23377304.

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Main article: Decaffeination Fibrous crystals of purified caffeine. Dark-field microscopy image, about 7mm × 11mm. Chocolate derived from cocoa beans contains a small amount of caffeine. The weak stimulant effect of chocolate may be due to a combination of theobromine and theophylline, as well as caffeine. [237] A typical 28-gram serving of a milk chocolate bar has about as much caffeine as a cup of decaffeinated coffee. By weight, dark chocolate has one to two times the amount of caffeine as coffee: 80–160mg per 100g. Higher percentages of cocoa such as 90% amount to 200mg per 100g approximately and thus, a 100-gram 85% cocoa chocolate bar contains about 195mg caffeine. [221] Tablets No-Doz 100mg caffeine tablets Tarnopolsky MA (2010). "Caffeine and creatine use in sport". Annals of Nutrition & Metabolism. 57 (Suppl 2): 1–8. doi: 10.1159/000322696. PMID 21346331. Modulation of adenosine receptor expression in the proximal tubule: a novel adaptive mechanism to regulate renal salt and water metabolism Am. J. Physiol. Renal Physiol. 1 July 2008 295:F35-F36

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Caffeine also causes the release of dopamine in the dorsal striatum and nucleus accumbens core (a substructure within the ventral striatum), but not the nucleus accumbens shell, by antagonizing A 1 receptors in the axon terminal of dopamine neurons and A 1– A 2A heterodimers (a receptor complex composed of 1 adenosine A 1 receptor and 1 adenosine A 2A receptor) in the axon terminal of glutamate neurons. [169] [164] During chronic caffeine use, caffeine-induced dopamine release within the nucleus accumbens core is markedly reduced due to drug tolerance. [169] [164] Enzyme targets In addition to its activity at adenosine receptors, caffeine is an inositol trisphosphate receptor 1 antagonist and a voltage-independent activator of the ryanodine receptors ( RYR1, RYR2, and RYR3). [167] It is also a competitive antagonist of the ionotropic glycine receptor. [168] Effects on striatal dopamine Panza F, Solfrizzi V, Barulli MR, Bonfiglio C, Guerra V, Osella A, etal. (March 2015). "Coffee, tea, and caffeine consumption and prevention of late-life cognitive decline and dementia: a systematic review". The Journal of Nutrition, Health & Aging. 19 (3): 313–28. doi: 10.1007/s12603-014-0563-8. hdl: 11586/145493. PMID 25732217. S2CID 8376733. Pure anhydrous caffeine is a bitter-tasting, white, odorless powder with a melting point of 235–238°C. [10] [11] Caffeine is moderately soluble in water at room temperature (2g/100 mL), but very soluble in boiling water (66g/100 mL). [193] It is also moderately soluble in ethanol (1.5g/100 mL). [193] It is weakly basic (pK a of conjugate acid = ~0.6) requiring strong acid to protonate it. [194] Caffeine does not contain any stereogenic centers [195] and hence is classified as an achiral molecule. [196]

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Schmidt B, Roberts RS, Davis P, Doyle LW, Barrington KJ, Ohlsson A, Solimano A, Tin W (May 2006). "Caffeine therapy for apnea of prematurity". The New England Journal of Medicine. 354 (20): 2112–21. doi: 10.1056/NEJMoa054065. PMID 16707748. S2CID 22587234. Archived from the original on 22 April 2020 . Retrieved 19 September 2018. O'Callaghan F, Muurlink O, Reid N (7 December 2018). "Effects of caffeine on sleep quality and daytime functioning". Risk Management and Healthcare Policy. 11: 263–271. doi: 10.2147/RMHP.S156404. PMC 6292246. PMID 30573997. a b Fintel M, Langer GA, Duenas C (November 1984). "Effects of low sodium perfusion on cardiac caffeine sensitivity and calcium uptake". Journal of Molecular and Cellular Cardiology. 16 (11): 1037–1045. doi: 10.1016/s0022-2828(84)80016-4. PMID 6520875.