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20-September-2008 09:55:50 - Theobromine Theobromine Systematic IUPAC name 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione Identifiers CAS number 83-67-0 ATC code C03BD01 R03DA07 PubChem 5429 Chemical data Formula C7H8N4O21 Mol. mass 180.164 g/mol SMILES eMolecules PubChem Synonyms xantheose diurobromine 3,7-dimethylxanthine Pharmacokinetic data Bioavailability ? Metabolism Hepatic demethylation and oxidation2 Half life 7.1 +/- 0.7 hours Excretion Renal 10% unchanged, rest as metabolites2 Therapeutic considerations Pregnancy cat. ? Legal status Uncontrolled substance Routes Oral Theobromine, also known as xantheose,1 is a bitter alkaloid of the cacao plant, found in chocolate. 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 name of the genus of the cacao tree, which itself is made up of the Greek roots theo God and brosi food, meaning food of the gods4 with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds.5 Theobromine is a water insoluble, crystalline, bitter powder; the colour has been listed as either white or colourless.6 It has a similar, but lesser, effect to caffeine, making it a lesser homologue. Theobromine is an isomer of theophylline as well as paraxanthine. Theobromine is categorized as a dimethyl xanthine,7 which means it is a xanthine8 with two methyl groups.9 Theobromine was first discovered in 184110 in cacao beans by Russian chemist Alexander Woskresensky. Theobromine was first isolated from the seeds of the cacao tree in 187811 and then shortly afterwards was synthesized from xanthine by Hermann Emil Fischer.12 Contents 1 Sources 2 Therapeutic uses 3 Pharmacology 4 Effects 4.1 Humans 4.2 Animals 4.3 Other 5 See also 6 References 7 Further reading Sources A chocolate bar and melted chocolate. Chocolate is made from the cacao bean, which is a natural source of theobromine. A chocolate bar and melted chocolate. Chocolate is made from the cacao bean, which is a natural source of theobromine. Theobromine is the primary alkaloid found in cocoa and chocolate. Cocoa powder such as Hershey's cocoa contains 108mg of or 2.16% theobromine per tablespoon 5g of powder.13 However, cocoa powder with more concentrated amounts of theobromine up to at least 10% also exists.14 Chocolate contains 0.5-2.7% theobromine, although white chocolate contains only trace amounts.15 Theobromine can also be found in small amounts in the kola nut 1.0-2.5%, the guarana berry, and the tea plant.16 The plant species with the largest amounts of theobromine are:17 Theobroma cacao Theobroma bicolor Yerba mate Camellia sinensis Cola acuminata Theobroma angustifolium Guarana Coffea arabica The mean theobromine concentrations in cocoa and carob products are:18 Item Mean theobromine content mg/g Cocoa 20.3 Cocoa cereals 0.695 Chocolate bakery products 1.47 Chocolate toppings 1.95 Cocoa beverages 2.66 Chocolate ice creams 0.621 Chocolate milks 0.226 Carob products 0-0.504 Therapeutic uses Following its discovery in the late 19th century, theobromine was put to use by 1916, where it was recommended by the publication Principles of Medical Treatment as a treatment for edema excessive liquid in parts of the body, syphilitic angina attacks, and degenerative angina.19 The American Journal of Clinical Nutrition notes that theobromine was once used as a treatment for other circulatory problems including arteriosclerosis, certain vascular diseases, angina pectoris, and hypertension.20 In modern medicine, theobromine is used as a vasodilator a blood vessel widener, an aid in urinating, and heart stimulant.1 In addition, the future use of theobromine in such fields as cancer prevention has been patented.21 Theobromine has also been used in birth defect experiments involving mice and rabbits. A decreased fetal weight was noted in rabbits following forced feeding, but not after other administration of theobromine. Birth defects were not seen in rats.22 Pharmacology Even without dietary intake, theobromine may occur in the body as it is a product of the human metabolism of caffeine which is metabolised in the liver into 10% theobromine, 4% theophylline, and 80% paraxanthine.23 In the liver, theobromine is metabolized into methylxanthine and subsequently into methyluric acid.24 Important enzymes include CYP1A2 and CYP2E1.25 As a methylated xanthine, theobromine is a potent Cyclic adenosine monophosphate cAMP phosphodiesterase inhibitor;8 this means that it helps prevent the enzyme phosphodiesterase from converting the active cAMP to an inactive form.26 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.27 Effects Humans A diagram of the bronchus. The loosening of the muscles in the bronchus caused by theobromine helps alleviate the symptoms of asthma. A diagram of the bronchus. The loosening of the muscles in the bronchus caused by theobromine helps alleviate the symptoms of asthma. While theobromine and caffeine are similar in that they are related alkaloids, theobromine is weaker in both its inhibition of cyclic nucleotide phosphodiesterases and its antagonism of adenosine receptors28. Therefore, theobromine has a lesser impact on the human central nervous system than caffeine. However, theobromine stimulates the heart to a greater degree.citation needed While theobromine is not as addictive, it has been cited as possibly causing addiction to chocolate.29 Theobromine has also been identified as one of the compounds contributing to chocolate's reputed role as an aphrodisiac.30 As it is a myocardial stimulant as well as a vasodilator, it increases heartbeat, yet it also dilates blood vessels, causing a reduced blood pressure.31 However, a recent paper published suggested that the decrease in blood pressure may be caused by flavanols.20 Furthermore, its draining effect allows it to be used to treat cardiac failure, which can be caused by an excessive accumulation of fluid.31 A 2004 study published by Imperial College London concluded that theobromine has an antitussive cough-reducing effect superior to codeine by suppressing vagus nerve activity.32 In the study, theobromine significantly increased the capsaicin concentration required to induce coughs when compared with a placebo.32 Additionally, theobromine is helpful in treating asthma since it relaxes the smooth muscles, including the ones found in the bronchi.33 A study conducted in Utah between 1983 and 1986, and published in 1993, showed a possible association between theobromine and an increased risk of suffering from prostate cancer in older men.34 This association was not found to be linear for aggressive tumors.34 While the association may be spurious, it is plausible.34 Theobromine can cause sleeplessness, tremors, restlessness, anxiety, as well as contribute to increased production of urine.33 Additional side effects include loss of appetite, nausea, and vomiting.35 Animals 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 of chocolate for a smaller dog and 400 grams for an average-sized dog. The same risk is reported for cats as well, although cats are less likely to ingest sweet food, having no sweet taste receptors. Complications include digestive issues, dehydration, excitability, and a slow heart rate. Later stages of theobromine poisoning include epileptic-like seizures and death. If caught early on, theobromine poisoning is treatable.36 Although not usual, the effects of theobromine poisoning can become fatal. Other Theobromine is known to induce gene mutations in lower eukaryotes and bacteria. At the time of a 1997 report by the IARC, genetic mutations had not been found in higher eukaryotes, such as humans.37 See also History of chocolate Theobromine poisoning References ^ 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 ion. 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. ^ 1 ^ Walter Sneader 2005. Drug Discovery: A History. John Wiley Sons. ISBN 0471899801. ^ Thomas Edward Thorpe 1902. Essays in Historical Chemistry. The MacMillan Company. ^ Theobromine content of Hershey's confectionery products. The Hershey Company. Retrieved on 2008-04-07. ^ AmerMed cocoa extract with 10% theobromine. AmerMed. Retrieved on 2008-04-13. ^ America Is Going Sweet on White Chocolate - New York Times ^ Sir Ghillean Prance, Mark Nesbitt 2004. The Cultural History of Plants. New York: Routledge, 137, 175, 178-180. ISBN 0415927463. ^ Activities of a Specific Chemical Query - Theobromine. United States Department of Agriculture. Retrieved on 2007-02-23. ^ Craig, Winston J.; Nguyen, Thuy T. 1984. Caffeine and theobromine levels in cocoa and carob products. Journal of Food Science 49 1: 302-303. doi:10.1111/j.1365-2621.1984.tb13737.x. Retrieved on 2008-04-20. 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. ^ George Cheever Shattuck 1916. Principles of medical treatment. W.M. Leonard, 15, 39, 41. ^ a b Kelly, Caleb J August 2005. Effects of theobromine should be considered in future studies. American Journal of Clinical Nutrition 82 2: 486-8. ^ US patent 6693104, Theobromine with an anti-carcinogenic activity, granted 2004-02-17 ^ 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 ^ Caffeine. The Pharmacogenetics and Pharmacogenomics Knowledge Base. Retrieved on 2007-02-22. ^ Herbert H. Cornish and A. A. Christman 1957. A Study of the Metabolism of Theobromine, Theophylline, and Caffeine in Man. Department of Biological Chemistry, Medical School, University of Michigan. ^ Gates S, Miners JO March 1999. Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism. Br J Clin Pharmacol 47 3: 299-305. doi:10.1046/j.1365-2125.1999.00890.x. PMID 10215755. ^ Phosphodiesterase. On-Line Medical Dictionary. Retrieved on 2007-02-23. Inhibitor. 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. ^ 2001 in Joel Hardman Lee Limbird: Goodman Gilman's the pharmacological basis of therapeutics, 10th ed.. New York: McGraw-Hill, 745. ISBN 0-07-135469-7. ^ William Gervase Clarence-Smith 2000. Cocoa and Chocolate, 1765-1914. London: Routledge, 10, 31. ISBN 0415215765. ^ Kenneth Maxwell 1996. A Sexual Odyssey: From Forbidden Fruit to Cybersex. New York: Plenum, 38-40. ISBN 030645405X. ^ a b US patent 20050089584, Methods and compositions for oral delivery of Areca and mate' or theobromine, granted 2005-04-28 ^ a b Usmani, Omar S.; Belvisi, Maria G.; Patel, Hema J.; Crispino, Natascia; Birrell Mark A.; Korbonits, Márta; Korbonits, DezsÅ‘; Barnes, Peter J. November 17, 2004. Theobromine inhibits sensory nerve activation and cough. FASEB Journal 19 2: 231-3. doi:10.1096/fj.04-1990fje. PMID 15548587. Retrieved on 2008-07-04. The present study demonstrates that theobromine, a methylxanthine derivative present in cocoa, effectively inhibits citric acid induced cough in guinea-pigs in vivo. Furthermore, in a randomized, double-blind, placebo controlled study in man, theobromine suppresses capsaicin-induced cough with no adverse effects. We also demonstrate that theobromine directly inhibits capsaicin-induced sensory nerve depolarization of guinea-pig and human vagus nerve suggestive of an inhibitory effect on afferent nerve activation. ^ a b Irwin J. Polk 1997. All about Asthma: Stop Suffering and Start Living. New York: Insight Books, 100. ISBN 0306455692. ^ a b c Slattery, Martha L.; West, Dee W. 1993. Smoking, alcohol, coffee, tea, caffeine, and theobromine: risk of prostate cancer in Utah United States. Cancer Causes Control 4 6: 559-63. doi:10.1007/BF00052432. PMID 8280834. Compared with men with very low levels of theobromine intake, older men consuming 11 to 20 and over 20 mg of theobromine per day were at increased risk of prostate cancer odds ratio-OR for all tumors = 2.06, 95 percent confidence interval CI = 1.33-3.20, and OR = 1.47, CI = 0.99-2.19, respectively; OR for aggressive tumors -- 1.90, CI = 0.90-3.97, and OR -- 1.74, CI -- 0.91-3.32, respectively ^ Theobromine in French. BIAM 2000-03-29. Retrieved on 2007-06-10. ^ HEALTH WATCH: How to Avoid a Canine Chocolate Catastrophe!, The News Letter, 2005-03-01 ^ 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. Further reading Bender, David A.; Arnold E. Bender 1995. A Dictionary of Food and Nutrition. Oxford: Oxford University Press. ISBN 0198609612. v d e Antihypertensives C02 and diuretics C03 Sympatholytic agents Centrally acting/antiadrenergics α2 agonist Clonidine, Guanfacine, Methyldopa imidazoline receptor agonist Moxonidine, Rilmenidine adrenergic uptake inhibitor Rescinnamine, Reserpine Ganglion-blocking/nicotinic antagonist Mecamylamine, Trimethaphan Peripherally acting/antiadrenergics α1 blockers: Prazosin Indoramin Trimazosin Doxazosin Urapidil Guanidine derivatives: Betanidine Guanethidine Guanoxan Debrisoquine Guanoclor Guanazodine Guanoxabenz Vasodilators Diazoxide hydrazinophthalazine Hydralazine, Dihydralazine, Endralazine, Cadralazine Minoxidil Nitroprusside Phentolamine Other antihypertensives serotonin antagonist Ketanserin endothelin receptor antagonist Bosentan, Ambrisentan, Sitaxsentan MAOI Pargyline THI Metirosine Diuretics Low ceiling Thiazides at DCT Bendroflumethiazide Hydroflumethiazide Hydrochlorothiazide Chlorothiazide Polythiazide Trichlormethiazide Cyclopenthiazide Methyclothiazide Cyclothiazide Mebutizide Sulfonamides Quinethazone Clopamide Chlortalidone Mefruside Clofenamide Metolazone Meticrane Xipamide Indapamide Clorexolone Fenquizone Other Mersalyl Theobromine Cicletanine osmotic Mannitol, Urea carbonic anhydrase inhibitor at PT Acetazolamide High ceiling Loop diuretic at AL Bumetanide, Furosemide, Torasemide, Ethacrynic acid Potassium-sparing at CD ESC blockers Amiloride, Triamterene aldosterone antagonists Spironolactone, Eplerenone, Potassium canrenoate, Canrenone v d e Drugs for obstructive airway diseases: asthma/COPD R03 Adrenergics, inhalants Short acting β2-agonists Salbutamol/Levosalbutamol Fenoterol Terbutaline Pirbuterol Procaterol Bitolterol Rimiterol Carbuterol Tulobuterol Reproterol Long acting β2-agonists LABA Arformoterol Bambuterol Clenbuterol Formoterol Salmeterol Ultra LABA: Indacaterol other Epinephrine Hexoprenaline Isoprenaline Isoproterenol Orciprenaline Metaproterenol Glucocorticoids Beclometasone Budesonide Ciclesonide Fluticasone Mometasone Anticholinergics/ muscarinic antagonist Ipratropium Tiotropium Mast cell stabilizers Cromoglicate Nedocromil Xanthines Aminophylline Doxofylline Theobromine Theophylline Leukotriene antagonists Montelukast Pranlukast Zafirlukast Lipoxygenase inhibitor Zileuton Thromboxane receptor antagonists Ramatroban Seratrodast Combination products Budesonide/formoterol Fluticasone/salmeterol Ipratropium/salbutamol Retrieved from http://en..org/wiki/Theobromine Categories: Chocolate | IARC Group 3 carcinogens | Xanthines | Bitter compoundsHidden categories: All articles with statements | Articles with statements since May 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки Català Dansk Deutsch Español Français Hrvatski Italiano עברית Magyar Nederlands 日本語 ‪Norsk bokmÃ¥l‬ ‪Norsk nynorsk‬ Polski Português Română РуÑ?Ñ?кий Simple English SlovenÄ?ina Suomi Svenska УкраїнÑ?ька ä¸æ–‡ This page was last modified on 8 August 2008, at 16:26
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