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'''Theobromine''', also known as '''xantheose''', is the principal [[alkaloid]] of ''[[Theobroma cacao]]'' (cacao plant).<ref name="pubchem">{{cite web |title=Theobromine |url=https://pubchem.ncbi.nlm.nih.gov/compound/5429 |publisher=PubChem, US National Library of Medicine |access-date=3 September 2022 |date=27 August 2022}}</ref> Theobromine is slightly water-[[solubility|soluble]] (330 mg/L) with a bitter taste.<ref name=Hbk>{{cite book | vauthors = Smit HJ | chapter = Theobromine and the Pharmacology of Cocoa | title = Methylxanthines | series = Handbook of Experimental Pharmacology | volume = 200 | issue = <!-- none --> | pages = 201–234 | year = 2011 | pmid = 20859797 | doi = 10.1007/978-3-642-13443-2_7 | isbn = 978-3-642-13442-5 }}</ref> In industry, theobromine is used as an [[food additive|additive]] and precursor to some [[cosmetics]].<ref name=pubchem/> It is found in [[chocolate]], as well as in a number of other foods, including
==Structure==
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''Theobromine'' is derived from ''[[Theobroma]]'', the name of the [[genus]] of the cacao tree, with the suffix ''-ine'' given to alkaloids and other [[base (chemistry)|basic]] nitrogen-containing compounds.<ref name="dict-ine">{{cite book | chapter = -ine | title = The American Heritage Dictionary of the English Language, Fourth Edition | publisher = [[Houghton Mifflin Company]] | year = 2004 | chapter-url = http://dictionary.reference.com/browse/-ine | isbn = 978-0-395-71146-0 | access-date = 2007-02-23 | archive-date = 2016-03-03 | archive-url = https://web.archive.org/web/20160303171459/http://dictionary.reference.com/browse/-ine | url-status = live }}</ref> That name in turn is made up of the [[Greek (language)|Greek]] roots ''theo'' ("[[god]]") and ''broma'' ("food"), meaning "food of the gods".<ref name="worldofcaffeine">{{cite book | vauthors = Bennett AW, Bealer BK | title = The World of Caffeine: The Science and Culture of the World's Most Popular Drug | publisher = [[Routledge]], New York | year = 2002 | isbn = 978-0-415-92723-9 | url = https://archive.org/details/worldofcaffeines00benn }} (note: the book incorrectly states that the name "theobroma" is derived from Latin)</ref>
Despite its name, the compound contains no [[bromine]], which is based on Greek ''bromos'' ("stench").{{Cn|date=May 2024}}
==Sources==
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There are approximately {{Convert|60|mg|abbr = off|0}} of theobromine in {{Convert|1|oz|order = flip}} of milk chocolate,<ref name="USDA db milk chocolate entry">{{cite web |url=http://ndb.nal.usda.gov/ndb/foods/show/5924?qlookup=milk+chocolate&offset=&format=Full#id-1 |title=USDA Nutrient database, entries for milk chocolate |access-date=2012-12-29 |archive-date=2017-07-08 |archive-url=https://web.archive.org/web/20170708121554/https://ndb.nal.usda.gov/ndb/foods/show/5924?qlookup=milk+chocolate&offset=&format=Full#id-1 |url-status=dead }}</ref> while the same amount of dark chocolate contains about {{Convert|200|mg|abbr = off|0}}.<ref name="USDA db dark chocolate entry">{{cite web |url=https://fdc.nal.usda.gov |title=USDA Nutrient database, entries for dark chocolate |access-date=2012-11-07 }}</ref> Cocoa beans naturally contain approximately 1% theobromine.<ref>{{cite journal | vauthors = Kuribara H, Tadokoro S | title = Behavioral effects of cocoa and its main active compound theobromine: evaluation by ambulatory activity and discrete avoidance in mice | journal = Arukoru Kenkyu to Yakubutsu Izon = Japanese Journal of Alcohol Studies & Drug Dependence | volume = 27 | issue = 2 | pages = 168–179 | date = April 1992 | pmid = 1586288 }}</ref>
Plant species and components with substantial amounts of theobromine are:<ref name="arsgrin-theobromine">{{cite web| url=https://phytochem.nal.usda.gov/phytochem/chemicals/show/17073?et=| title=Theobromine content in plant sources| publisher=Dr. Duke's Phytochemical and Ethnobotanical Databases, [[United States Department of Agriculture]]| date=6 February 2019| access-date=9 March 2019| archive-date=8 May 2019| archive-url=https://web.archive.org/web/20190508200500/https://phytochem.nal.usda.gov/phytochem/chemicals/show/17073?et=| url-status=dead}}</ref><ref name=":4">{{cite journal |vauthors=Crown PL, Emerson TE, Gu J, Hurst WJ, Pauketat TR, Ward T |date=August 2012 |title=Ritual Black Drink consumption at Cahokia |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=109 |issue=35 |pages=13944–9 |doi=10.1073/pnas.1208404109 |pmc=3435207 |pmid=22869743 |doi-access=free}}</ref>
* ''[[Theobroma cacao]]'' – seed and [[Seed#Seed coat|seed coat]]
* ''[[Theobroma bicolor]]'' – seed coat
* ''[[Ilex paraguariensis]]'' – leaf
* ''[[Ilex guayusa]] – leaf''
* ''[[Ilex vomitoria]] – leaf''
* ''[[Camellia sinensis]]'' – leaf
Theobromine can also be found in trace amounts in the [[kola nut]], the [[guarana]] berry, [[yerba mate]] ([[Yerba Mate|''Ilex paraguariensis'']])
The mean theobromine concentrations in cocoa and [[carob]] products are:<ref>{{cite web |title=FoodData Central |url=https://fdc.nal.usda.gov/fdc-app.html#/food-details/169593/nutrients |website=fdc.nal.usda.gov}}</ref><ref name=Craig1984>{{cite journal| vauthors = Craig WJ, Nguyen TT | year = 1984| title = Caffeine and theobromine levels in cocoa and carob products| journal = [[Journal of Food Science]]| volume = 49| issue = 1| pages = 302–303| doi = 10.1111/j.1365-2621.1984.tb13737.x| quote = Mean theobromine and caffeine levels respectively, were 0.695 mg/g and 0.071 mg/g in cocoa cereals; 1.47 mg/g and 0.152 mg/g in chocolate bakery products; 1.95 mg/g and 0.138 mg/g in chocolate toppings; 2.66 mg/g and 0.208 mg/g in cocoa beverages; 0.621 mg/g and 0.032 mg/g in chocolate ice creams; 0.226 mg/g and 0.011 mg/g in chocolate milks; 74.8 mg/serving and 6.5 mg/serving in chocolate puddings.... Theobromine and caffeine levels in carob products ranged from 0–0.504 mg/g and 0-0.067 mg/g, respectively.}}</ref>
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===Animals===
Theobromine is the reason chocolate is poisonous to dogs. Dogs and other animals that [[metabolize]] theobromine (found in chocolate) more slowly<ref>{{cite web|url=http://www.merckmanuals.com/vet/toxicology/food_hazards/chocolate.html|title=Chocolate – Toxicology – Merck Veterinary Manual|access-date=23 December 2017|archive-date=12 July 2014|archive-url=https://web.archive.org/web/20140712005049/http://www.merckmanuals.com/vet/toxicology/food_hazards/chocolate.html|url-status=live}}</ref> can succumb to theobromine poisoning from as little as {{cvt|50|g|oz}} of [[milk chocolate]] for a smaller dog and {{cvt|400|g|oz}}, or around nine {{convert|1.55|oz|order=flip|adj=on}} small milk chocolate bars, for an average-sized dog. The concentration of theobromine in dark chocolates (about {{cvt|10|g/kg}}) is up to 10 times that of milk chocolate ({{cvt|1|to|5|g/kg}}), meaning dark chocolate is far more toxic to dogs per unit weight or volume than milk chocolate.{{Cn|date=May 2024}}
The [[median lethal dose]] of theobromine for dogs is {{cvt|100|–|200|mg/kg|}}; therefore, a {{cvt|10|kg|}} dog would need to consume a minimum of {{cvt|200|g|}} of the most theobromine-rich ({{cvt|5|g/kg|}}) dark chocolate, or a maximum of {{cvt|1|kg|}} (of theobromine-rich milk chocolate), to have a 50% chance of receiving a lethal dose. However, even {{cvt|40|g|}} of milk chocolate may induce vomiting and diarrhea.<ref>{{cite web |last1=Gwaltney-Brant |first1=Sharon |title=Chocolate Toxicosis in Animals |url=https://www.merckvetmanual.com/toxicology/food-hazards/chocolate-toxicosis-in-animals |website=Merck Veterinary Manual |publisher=Merck & Co., Inc. |access-date=24 December 2023}}</ref>
The same risk is reported for cats as well,<ref>{{cite web |url=http://aspcapro.org/sites/pro/files/m-toxbrief_0201_0.pdf |title=Chocolate intoxication |vauthors=Gwaltney-Brant S |publisher=[[American Society for the Prevention of Cruelty to Animals|ASPCA]] |website=aspcapro.org |access-date=23 December 2017 |archive-date=8 February 2017 |archive-url=https://web.archive.org/web/20170208145634/http://aspcapro.org/sites/pro/files/m-toxbrief_0201_0.pdf |url-status=dead}}</ref> although cats are less likely to ingest sweet food, as cats lack [[Sweetness#The sweetness receptor|sweet taste receptors]].<ref name=wired>{{cite magazine |url=https://wired.com/2013/02/the-poisonous-nature-of-chocolate |title=The Poisonous Chemistry of Chocolate |date=14 February 2013 |magazine=[[Wired (magazine)|Wired]] |access-date=12 March 2017 |archive-date=8 February 2017 |archive-url=https://web.archive.org/web/20170208145832/https://www.wired.com/2013/02/the-poisonous-nature-of-chocolate/ |url-status=live}}</ref> Complications include digestive issues, dehydration, excitability, and a slow heart rate. Later stages of theobromine poisoning include [[epilepsy|epileptic]]-like [[seizure]]s and death. If caught early on, theobromine poisoning is treatable.<ref name="healthwatchcanines">{{cite news | title=HEALTH WATCH: How to Avoid a Canine Chocolate Catastrophe! | newspaper=The News Letter | location=Belfast, Northern Ireland | date=2005-03-01}}</ref> Although not common, the effects of theobromine poisoning can be fatal.<ref name="wired" />
== See also ==
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