Talk:Theobromine

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The current Pharmacology Collaboration of the Month is Theobromine.
The previous collaboration was Melatonin.
Good article Theobromine was one of the Natural sciences good articles, but it has been removed from the list. There are suggestions below for improving the article to meet the good article criteria. Once these issues have been addressed, the article can be renominated. Editors may also seek a reassessment of the decision if they believe there was a mistake.
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    [edit] How does caffeine "increase stress"?

    This is not mentioned in the caffeine article. I sure would like to see a source.

    From the caffeine article: "Symptoms of caffeine intoxication include: restlessness, nervousness, excitement..." I guess that the general idea is that large doses of caffeine often induce stress-like symptoms. Caffeine in smaller doses has a slightly similar effect, but 'stress' is a very strong word for it.--Simen 88 13:39, 29 July 2006 (UTC)

    [edit] Why is there no bromine in the theobromine molecule?

    To call it theobromine, technically there must be bromine in the molecule. It is posssible that the diagram of the molecule of theobromine is incorrect. Chemically, it has no properties like that of bromine and probably does not look like it since bromine is a brown/red liquid which an indivisable chemical element.

    The name is derived from greek, as explained in the introduction. It is not a description of the formula.Simen 88 21:18, 17 October 2006 (UTC)
    Because God made it that way. Flying Hamster 20:21, 1 November 2007 (UTC)

    [edit] How is chocolate "safe for humans to consume in large quantities"?

    Could someone clarify the following statement, which is somewhat confusing: "In chocolate, theobromine exists in doses that are safe for humans to consume in large quantities"

    Read the whole statement:arge quantities, but can be lethal for animals such as dogs and horses, as they metabolize theobromine more slowly."

    I suggest:
    "Very high levels of theobromine can be dangerous to some mammals. Humans metabolise theobromine quickly, making it almost impossible to suffer harm from theobromine poisoning due to excessive chocolate consumption. Other animals, including horses and dogs, metabolise theobromine much more slowly, so even moderate chocolate consumption can be fatal."
    but a better version yet would say why and how:
    "Very high levels of theobromine can be dangerous because XXXX. Humans metabolise theobromine quickly (broken down by the liver or what?), making it almost impossible to suffer harm from theobromine poisoning due to excessive chocolate consumption. Other animals, including horses and dogs, metabolise theobromine much more slowly, so even moderate chocolate consumption can be fatal."
    Can someone explain the pathology and metabolism, to fill out my latter suggestion? -- Finlay McWalter | Talk 21:14, July 19, 2005 (UTC)

    [edit] Could we get a correct molecular structure for Theobromine on this page?

    I just did an elemental analysis on the ball and stick Theobromine molecule on my desk and found that, contrary to the Theobromine chemical structure picture we offer to readers, there are 7 carbons and 8 hydrogens in the Theobromine molecule. I am in the middle of a chimpanzee agonistic political turf battle right now myself, but the next time I take a coffee break, I will put two methyl groups on the two sticks with no balls.  :)) Would you agree that this should be done? Perhaps, we could just start with the caffeine molecule Caffeine molecular structure and replace the methyl group between the two carbonyls with a hydrogen. What do you think? ---Rednblu | Talk 16:08, 3 September 2005 (UTC)

    Why? The "sticks with no balls" clearly terminate in methyl groups; anything else would need to be shown, but the methyl groups come as standard. EdC 22:01, 18 April 2006 (UTC)

    [edit] From PNA/Chemicals

    • Theobromine need a check on teratogenicity and mutagenicity

    the article is not clear. I've removed Theobromine from Category:Teratogens --Melaen 21:55, 25 February 2006 (UTC)

    [edit] Caffeine article says that caffeine is metabolized to it

    The Caffeine article says that caffeine is metabolized to three components one of which is theobromine. If that's true, shouldn't this article reflect that. Here I read theobromine has very different effects from caffeine. In that case that statement wouldn't be very precise would it. --Fs 11:48, 17 March 2006 (UTC)

    [edit] Vector drawing of theobromine

    I'm looking to do up a vector version of image:theobromine.png, based on image:theophylline.png. I just want to check one thing: is the H on the nitrogen at left needed or would it be implicit if left off? -- Perey 07:28, 9 September 2006 (UTC)

    [edit] common saying

    Many people say that theobromine is the ingredient in chocolate that has the same effect as "falling in love." Any idea where that all comes from?66.41.66.213 04:34, 5 November 2006 (UTC)

    I can't find any concrete information on theobromine having this effect, but it is well known that it is mood-enhancing. I did, however, find this. I assume some people have drawn a connection between theobromine's effects and chocolate's effects.Simen 88 14:20, 26 November 2006 (UTC)

    [edit] Prostate cancer

    From the abstract of the article by Slattery and West it is clear that the theobromine intake was purely from chocolate (I think there are not that many people who take theobromine as a supplement). Couldn't the higher risk of prostate cancer be caused by some other substance in chocolate or is there other evidence pointing at theobromine? Icek 12:25, 28 January 2007 (UTC)

    It is know that fat is associated with prostate cancer, so it could be from all that fat in chocolate for all we know. In any case, the evidence wasn't very strong, and could be spurious. Also, the increased risk was shown to be for older persons only.
    As for other evidence pointing to theobromine, as per the article, it is known to be genotoxic in lower animals in various ways. Nonetheless and fortunately, it is not too difficult to reduce one's risk of acquiring prostate cancer.
    I wouldn't worry too much before popping a cocoa powder pill (and acquiring the theobromine contained within). People have been consuming cocoa for a very long time, and there are health benefits to it.
    --AB (talk) 17:35, 7 April 2008 (UTC)

    [edit] GA review

    Pretty good article, although there are a few issues which preclude its listing as a GA right now:

    1. Methylxanthine family—there isn't really a black-letter chemical "taxonomy" of this sort AFAIK, so I'd reword it to "the methylxanthine class of chemical compounds" or something to that effect.
    2. Under "Properties", you can link "inhibitor" to either enzyme inhibitor or phosphodiesterase inhibitor, not just "inhibitor". "Homologue" should be linked to homologous series.
    3. Please add ISBNs to all book references.
    4. Please italicize all scientific names as per MoS:T.
    5. I'd like to see some History—when it was first isolated, synthesized, etc. Maybe a little bit more on the history of cocoa/chocolate and its effects.
    6. Can you find data to fill in the Drugbox? It is painfully empty right now.

    Otherwise, it's good. When these issues are addressed, it will be Good :) Fvasconcellos 14:26, 28 February 2007 (UTC)

    If you don't mind, I'm going to cross out your points as you go along. I'll do my best to continue research on it. And of course, I will find the ISBNs. I'm sure the books are legitimate; I've gotten them from this really cool online library. I should get back to work. —Signed, your friendly neighborhood MessedRocker. 21:17, 28 February 2007 (UTC)
    Go ahead and strike them through. Nice work so far. Fvasconcellos 21:37, 28 February 2007 (UTC)
    By the way, what constitutes a scientific name? —Signed, your friendly neighborhood MessedRocker. 21:18, 28 February 2007 (UTC)
    Names of species and genera—see Binomial nomenclature. Fvasconcellos 21:37, 28 February 2007 (UTC)
    Ohh, those scientific names. Anyways, I italicised their names. All we have left to do is create some sort of history section, then the article will be ready for Good Articledom! —Signed, your friendly neighborhood MessedRocker. 02:33, 1 March 2007 (UTC)
    Yes, those' :) Almost there, keep up the good work. I like to see tag-teaming improvement! Fvasconcellos 14:09, 1 March 2007 (UTC)

    [edit] GA fail

    Sorry, but for the moment I am failing this article's GA nomination. Although it is well referenced and pretty well written, it could still be broader in scope. I realize GAC is meant for short articles, but this merits expansion IMHO. Thanks for your work so far and best wishes, Fvasconcellos 00:06, 8 March 2007 (UTC)

    [edit] two critiques

    I was sort of reviewing this article for GA status, and I think it is good in most respects, but I saw a couple of things that concerned me:

    • It the phrase, "A lesser homologue of caffeine...", what does lesser mean?
    • I am not sure that in makes sense to have the diagram of the bronchus in this article; it really only illustrates one sentence.

    Good luck and good work. ike9898 20:00, 28 May 2007 (UTC)

    I suppose a "lesser homologue" as in it has a lesser effect on living beings yet the two drugs are nonetheless very similar. —Signed, your friendly neighborhood MessedRocker. 22:09, 28 May 2007 (UTC)
    If that is the case, surely "less active" is more precise. Flying Hamster (talk) 13:57, 5 April 2008 (UTC)

    [edit] GA nomination Critique

    The reason I've put this article on hold is that, like the previous reviewer, I think it could do with slightly more material. I would suggest:

    • A little more about social use. The previous reviewer did suggest this. Personally, I came to the article expecting to see it clearly stated at the top that this is the main active ingredient in chocolate. (That's what made me pick this to review in the first place.) If you feel it is inappropriate to go into detail on the history of chocolate use, then maybe go through the other chocolate-related articles and find a good one to direct readers to.
    • I would suggest looing at Wikipedia:WikiProject Pharmacology/Style guide and adding in what you judge to be the most appropriate headings mentioned there. This drug doesn't need the heaviest treatment, but I was surprised, for example, to see mention that caffeine is partially metabolised to theobromine, but no mention of how theobromine is metabolised. As theobromine appears to be prescribed in some countries, I would expect a more detailed discussion of things like side-effects, administration etc. The French webpage already cited in the article[1] appears to have the information needed, but my French isn't good enough and I'm an ex-drug worker social worker not a pharmacologist, so you or someone else will have to translate.

    Otherwise it looks a well put-together little article. I tried to BE BOLD and fix a little language problem at the top. It read as if the genus was made up of Greek roots, not the name of the genus. I may have made the English worse in other ways, however. And if "lesser homologue" confused the other potential reviewer, I suggets that the JARGON be explaine or replaced --Peter cohen 00:55, 9 June 2007 (UTC)

    I disagree that the article needs to go into extensive detail about the social use of theobromine, as it's more tied into the use of chocolate and this is an article about theobromine not chocolate. As for the French article, I'll see if I can read it. (messedrocker • talk) 02:12, 9 June 2007 (UTC)
    I have started to do some cleaning up. I am now looking at that French article and perhaps I will be updating the article with information from it. (messedrocker • talk) 02:50, 9 June 2007 (UTC)
    That article doesn't really have much more than what the Wikipedia article already has. In any case, I am finished editing for the night. Tomorrow I shall continue; I have some other source material on hand which should help contribute to the article. (messedrocker • talk) 04:30, 9 June 2007 (UTC)
    I think you're more or less there. But I'm not stopping you doing what else you were going to polish. I've gone and explained the two bits of unexplained jargon that most leapt out at me. Remember the primary use of pharmacology articles in wiki will be by people prescribed drugs and concerned relatives. Professionals will have the British National Formulary, MIMS - prescribing reference or their equivalents in other countries. Obviously this article will also attract chocoholics like me. --Peter cohen 08:13, 9 June 2007 (UTC)
    I think with your changes above and the reduction of jargon we have achieved that I can now go over to te nominations page and pass this article. --Peter cohen 19:02, 11 June 2007 (UTC)

    [edit] Please check this article

    There is an inappropriate image that comes up over the introductory paragraph.

    Someone must have vandalized the infobox template. Thank you for informing us. (messedrocker • talk) 00:17, 29 June 2007 (UTC)

    [edit] cleanup-rewrite tag

    I'm tagging this because it needs to be rewritten. There is little organization to the article and some of the information is repeated several times. It is very confusing, even to this chemist. Jeff Dahl 04:21, 6 October 2007 (UTC)

    [edit] Discussion of Good Article Reassessment

    Nominating this article for GAR. As noted on the peer review last week, this article needs to be rewritten, because it currently is not well organized. This article needs to follow wikipedia's medical manual of style for drug-related articles. Many of the sections seem too short, without enough context, and it needs to have better coverage of topics such as its metabolism and biosynthesis. Terms like "lesser homologue" need to be changed; other reviewers have had problems with terms like this as well. The peer review contains more suggestions for improvement, and I will happy to review this article again in the future. Jeff Dahl 04:58, 6 October 2007 (UTC)

    This has now been delisted. See the archived discussion (linked from article history) for further suggestions. Geometry guy 21:26, 30 October 2007 (UTC)

    [edit] Animals and Chocolate

    The current information under "4.2 Animals" is too vague to be useful and could cause wrong impressions/assumtions in my opinion. The Theobromine poisoning article has somewhat more useful information and I think we could draw a short few statements from it. —Preceding unsigned comment added by ASA-IRULE (talk • contribs) 15:33, 26 November 2007 (UTC)

    I think there should be a merger, except last time I checked, theobromine poisoning was largely unsourced. MessedRocker (talk) (write this article) 19:58, 26 November 2007 (UTC)

    The section still needs work. The part about poisoning dogs is alarmist, inaccurate and poorly sourced. — NRen2k5 —Preceding comment was added at 14:58, 31 December 2007 (UTC)

    [edit] Concentrations

    0.5% - 2.7% for chocolate seems a bit too much. According to V. Beasley, the concentration in coca beans is only 1% - 2% and in dark chocolate it's no more than 0.5%. Icek (talk) 02:06, 16 December 2007 (UTC)

    [edit] Pharmacology Collaboration of the Month

    The collaboration of the month program for WP:PHARM has been 'resurrected' in 2008! The new collaboration is Melatonin. Please help bring it up to featured or good article status. Theobromine remains a nominee at this point (I've extended the deadline). Dr. Cash (talk) 17:42, 14 January 2008 (UTC)

    This article is now the current Pharmacology Collaboration of the Month for March 2008. Dr. Cash (talk) 18:47, 4 March 2008 (UTC)

    [edit] etymology is wrong

    Theobromine is from from theo- and *broma* (food), not *brosi* (I would bet the writer was thinking of the etymology of ambrosia and sliipped up). I don't know if this mistake is also in the book cited in footnote 4, but the OED 3rd edition could be cited for the correct etymology. —Preceding unsigned comment added by 71.232.13.245 (talk) 23:40, 21 January 2008 (UTC)

    [edit] Missing Information

    "Theobromine is known to induce gene mutations in lower eukaryotes and bacteria." - This needs a reference. Only reference given is related to lack of carcinogenic activity in humans and experimental animals. This should be removed if no reference can be found.

    "and then shortly afterwards was synthesized from xanthine by Hermann Emil Fischer.[11]" - Anyone have a date for the synthesis?

    Additionally, I've seen several sources stating that Theobromine was isolated by Woskresensky in 1841 rather than in 1878. One source which explicitly states that 1878 is an incorrect date for the isolation of Theobromine: Molecular Interventions 7:236-242, (2007), A New Look at the Xanthine Alkaloids by Stanley Scheindlin --Jmcclare (talk) 19:54, 10 March 2008 (UTC)

    [edit] Coughs and capsaicin concentration

    I'm a layman looking into the effects of caffeine & chocolate on my body. The following text is confusing me: "...theobromine has an antitussive (cough-reducing) effect... theobromine significantly increased the capsaicin concentration required to induce coughs when compared with a placebo." This leads me to think capsaicin makes you cough & theobromine increases the concentration of capaicin.

    If theobromine reduces cough shouldn't it either "decrease the capsaicin concentration required to induce coughs" or "increase the capsaicin concentration required to reduce coughs"? wbm (talk) 21:15, 23 April 2008 (UTC)

    I think (I'm another layman) that what it is intended to mean is that to get a person to cough you need to give them a hotter chilli (i.e. with a greater concentration of capsaicin) after they've had some theobromine than you would have without the theobromine.--Peter cohen (talk) 21:26, 23 April 2008 (UTC)
    Peter is correct. --AB (talk) 23:15, 23 April 2008 (UTC)

    [edit] Theobromine supplement

    Does anyone know of a theobromine supplement in doses of 100/500/1000 mg? The best I currently know is AmerMed cocoa extract with 10% theobromine, but that's far from ideal. One problem with taking too much cocoa extract can be that the extract also contains unwanted caffeine. The AmerMed product in particular is advertised as containing 0.18% caffeine, which is negligible. --AB (talk) 23:19, 23 April 2008 (UTC)

    [edit] Less active - source?

    The source for the statement that theobromine is less active than caffeine seems to be this book: Kenneth Maxwell (1996). A Sexual Odyssey: From Forbidden Fruit to Cybersex. New York: Plenum, 38-40. ISBN 030645405X. I looked it up in that book and found that it references a (very old - 1970's version of Goodman & Gilman: The Pharacological basis of theapeutics 4th ed. In the 10th edition (2001) version of that book: Joel Hardman & Lee Limbird (2001). Goodman & Gilman's the parcological basis of therapeutics. 10th ed. New York: McGraw-Hill, ISBN 0-07-135469-7, the only mention of theobromine is during a discussion of the related compound theophylline. It states: [methylxanthines] "inhibit cyclic nucleotide phosphodiesterases" [and] "antagonize receptor-mediated actions of adenosine" ... [for both effects] "the order of potency for the naturally occurring methyxanthines is theophylline > caffeine > theobromine". I find no mention of theobromine having a greater effect on the heart. Should the reference be updated? Is a source available for the claim that theobromine has a greater effect on the heart? Xargque (talk) 00:33, 15 May 2008 (UTC)

    Source updated Xargque (talk) 19:59, 22 May 2008 (UTC)