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Theobromine
From Wikipedia, the free encyclopedia
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Theobromine
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| Systematic (IUPAC) name | |
| 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione | |
| Identifiers | |
| CAS number | |
| ATC code | C03 R03DA07 |
| PubChem | |
| Chemical data | |
| Formula | C7H8N4O2[1] |
| Mol. mass | 180.164 g/mol |
| SMILES | search in , |
| Synonyms | xantheose diurobromine 3,7-dimethylxanthine |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | Hepatic demethylation and oxidation[2] |
| Half life | 7.1 +/- 0.7 hours |
| Excretion | Renal (10% unchanged, rest as metabolites)[2] |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status |
Uncontrolled substance |
| Routes | Oral |
Theobromine, also known as xantheose,[1] is a bitter alkaloid of the cacao plant. It is in the methylxanthine class of chemical compounds,[3] which also includes the similar compounds theophylline and caffeine.[1] Despite its name, the compound contains no bromine — theobromine is derived from Theobroma, the genus of the cacao tree, which is composed of the Greek roots theo ("God") and broma ("food"), meaning "food of the gods",[4] with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds.[5]
Contents |
Theobromine has been described as a water insoluble, crystalline, bitter powder; the colour has been listed as either white or colourless.[6] A lesser homologue of caffeine, theobromine is an isomer of theophylline as well a ureide. Theobromine is categorized as a dimethyl xanthine,[7] which means it is a purine[8] with two methyl groups.[9]
As a methylated xanthine, theobromine is a potent cAMP phosphodiesterase inhibitor;[8] this means that it helps prevent the enzyme phosphodiesterase from converting the active cAMP to an inactive form.[10] Cyclic Adenosine Monophosphate, or cAMP, works as a second messenger in many hormone- and neurotransmitter-controlled metabolic systems, such as the breakdown of glycogen. When the inactivation of cAMP is inhibited by a compound such as theobromine, the effects of the neurotransmitter or hormone which stimulated the production of cAMP are much longer lived. The net result is generally a stimulatory effect.[11]
Theobromine is the primary alkaloid found in cocoa and chocolate; chocolate contains 0.5-2.7% theobromine. Theobromine can also be found in small amounts in the kola nut (1.0-2.5%), the guarana berry, and the tea plant.[12]
In the human liver, caffeine is metabolised by enzymes into 10% theobromine, 4% theophylline, and 80% paraxanthine.[13]
The plant species with the most amount of theobromine are:[14]
- Theobroma cacao
- Theobroma bicolor
- Ilex paraguariensis
- Camellia sinensis
- Cola acuminata
- Theobroma angustifolium
- Paullinia cupana
- Coffea arabica
While theobromine and caffeine are similar in that they're related alkaloids, theobromine has a lesser impact on the human central nervous system though it stimulates the heart to a greater degree.[15] While theobromine is not as addictive, it has been cited as possibly causing addiction to chocolate.[16] A Sexual Odyssey: From Forbidden Fruit to Cybersex discusses how chocolate's alleged aphrodisiac effects may be caused by a number of factors. These include the stimulative effects of theobromine, pleasure induced by the hypothalamus as an effect of chocolate's sweet and fatty nature, or how chocolate affects the levels of serotonin. While serotonin has a pleasurable effect, in high concentrations it can be converted to melatonin which in large amounts reduces sexual drive.[15]
In medicine, it is used as a vasodilator, diuretic, and myocardial stimulant.[1] A 2005 study published by Imperial College London concluded that theobromine has an antitussive effect superior to codeine by suppressing vagus nerve activity.[17] Additionally, theobromine is helpful in treating asthma since it relaxes the smooth muscles, including the ones found in the bronchi.[18]
There is a possible association between theobromine and an increased risk of suffering from prostate cancer.[19] Like all xanthines, theobromine can cause "sleeplessness, tremors, restlessness, and anxiety," as well as contribute to diuresis.[18]
The amount of theobromine found in chocolate is small enough that it can be safely consumed by humans, but animals that metabolize theobromine more slowly, such as dogs, can succumb to theobromine poisoning from as little as 50 grams for a smaller dog and 400 grams for an average-sized dog. Complications include digestive issues, dehydration, excitability, and a slow heart rate. Later stages of theobromine poisoning include epileptic-like seizure and possibly death. If caught early on, theobromine poisoning is treatable.[20]
Theobromine is known to induce gene mutations in lower eukaryotes and bacteria. At the time of a 1997 report by the IARC, mutations had not been found in higher eukaryotes, such as humans.[21]
Theobromine is used as an experimental teratogen in mice and rabbits.[22]
- ^ a b c d William Marias Malisoff (1943). Dictionary of Bio-Chemistry and Related Subjects. Philosophical Library, 311, 530, 573. ISBN B0006AQ0NU.
- ^ a b (French) Theobromine. BIAM (March 29, 2000). Retrieved on 2007-03-01.
- ^ Baer, Donald M.; Elsie M. Pinkston (1997). Environment and Behavior. Westview Press, 200.
- ^ Bennett, Alan Weinberg; Bonnie K. Bealer (2002). The World of Caffeine: The Science and Culture of the World's Most Popular Drug. Routledge, New York. ISBN 0415927234. (note: the book incorrectly notes that the name "Theobroma" is derived from Latin)
- ^ "-ine." (2004) The American Heritage® Dictionary of the English Language, Fourth Edition. Houghton Mifflin Company. ISBN 0395711460.
- ^ theobromine. Dictionary.com. Retrieved on 2007-02-22. For convenience, the direct source of the three definitions used has been cited.
- ^ Theobromine. On-Line Medical Dictionary. Retrieved on 2007-02-23.
- ^ a b Xanthine. On-Line Medical Dictionary. Retrieved on 2007-02-23.
- ^ Dimethyl. On-Line Medical Dictionary. Retrieved on 2007-02-23.
- ^ * Phosphodiesterase. On-Line Medical Dictionary. Retrieved on 2007-02-23.
- ^ David L. Nelson, Michael M. Cox (2005). Lehninger Principles of Biochemistry. W.H. Freeman and Company, 435–439. ISBN 0716743396.
- ^ Sir Ghillean Prance, Mark Nesbitt (2004). The Cultural History of Plants. New York: Routledge. ISBN 0415927463.
- ^ Caffeine. The Pharmacogenetics and Pharmacogenomics Knowledge Base. Retrieved on 2007-02-22.
- ^ Activities of a Specific Chemical Query - Theobromine. United States Department of Agriculture. Retrieved on 2007-02-23.
- ^ a b Kenneth Maxwell (1996). A Sexual Odyssey: From Forbidden Fruit to Cybersex. New York: Plenum, 38-40. ISBN 030645405X.
- ^ William Gervase Clarence-Smith (2000). Cocoa and Chocolate, 1765-1914. London: Routledge, 10, 31. ISBN 0415215765.
- ^ Usmani O; Belvisi M, Patel H, Crispino N, Birrell M, Korbonits M, Korbonits D, Barnes P (2005). "Theobromine inhibits sensory nerve activation and cough.". FASEB J 19 (2): 231-3. PMID 15548587.
- ^ a b Irwin J. Polk (1997). All about Asthma: Stop Suffering and Start Living. New York: Insight Books, 100. ISBN 0306455692.
- ^ Slattery M, West D (1993). "Smoking, alcohol, coffee, tea, caffeine, and theobromine: risk of prostate cancer in Utah (United States).". Cancer Causes Control 4 (6): 559-63. PMID 8280834.
- ^ 2005-03-01, "HEALTH WATCH: How to Avoid a Canine Chocolate Catastrophe!", The News Letter
- ^ International Agency for Research on Cancer (November 17, 1991). Volume 51: Coffee, Tea, Mate, Methylxanthines and Methylglyoxal - Theobromine (PDF). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. WHO. Retrieved on 2006-09-19.
- ^ Rambali B, Andel I van, Schenk E, Wolterink G, Werken G van de, Stevenson H, Vleeming W (2002). "[The contribution of cocoa additive to cigarette smoking addiction]" (PDF). RIVM (report 650270002/2002). - The National Institute for Public Health and the Environment (Netherlands)
- Bender, David A.; Arnold E. Bender (1995). A Dictionary of Food and Nutrition. Oxford: Oxford University Press. ISBN 0198609612.
| Antihypertensives (C02) and diuretics (C03) | |
|---|---|
| Antiadrenergic agents (including alpha) | Clonidine, Doxazosin, Guanethidine, Guanfacine, Lofexidine,Mecamylamine, Methyldopa, Moxonidine, Prazosin, Rescinnamine, Reserpine |
| Vasodilators | Diazoxide, Hydralazine, Minoxidil, Nitroprusside, Phentolamine |
| Other antihypertensives | Bosentan, Ketanserin |
| Low ceiling diuretics | Bendroflumethiazide, Chlorothiazide, Chlortalidone, Hydrochlorothiazide, Indapamide, Quinethazone, Mersalyl, Metolazone, Theobromine, Cicletanine |
| High ceiling diuretics | Bumetanide, Furosemide, Torasemide |
| Potassium-sparing diuretics | Amiloride, Eplerenone, Spironolactone, Triamterene |
| Medications commonly used in asthma and COPD (primarily R03) | |
|---|---|
| Anticholinergics | Ipratropium, Tiotropium |
| Short acting β2-agonists | Salbutamol, Terbutaline |
| Long acting β2-agonists (LABA) | Bambuterol, Clenbuterol, Fenoterol, Formoterol, Salmeterol |
| Corticosteroids | Beclometasone, Budesonide, Ciclesonide, Fluticasone |
| Leukotriene antagonists | Montelukast, Pranlukast, Zafirlukast |
| Xanthines | Aminophylline, Theobromine, Theophylline |
| Mast cell stabilizers | Cromoglicate, Nedocromil |
| Combination products | Budesonide/formoterol, Fluticasone/salmeterol, Ipratropium/salbutamol |