# Question about synthetic testosterone. **URL:** \ **Category:** Factual Questions\ **Created:** [August 6, 2006, 3:05pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561 "2006-08-06T15:05:00Z")\ **Posts on this page:** 20\ **Page:** 1
**Author:** ![solkoe](https://avatars.discourse-cdn.com/v4/letter/s/919ad9/32.png) [@solkoe](https://boards.straightdope.com/u/solkoe)\ **Post date:** [August 6, 2006, 3:05pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/1 "2006-08-06T15:05:00Z")
This is related to the Tour de France scandel. Apparently, Floyd Landis was caught because some of the testosterone in his body was not his own. This leads me to ask, how is testosterone synthesized artificially? I’m going to guess that testosterone is quite a complex molecule and would be difficult to make from scratch in a lab. Perhaps it is modified from an already plentiful molecule. How is this man made testosterone different from natural testosterone? Is it possible to extract testosterone from another person, use it in competition and not be caught by drug tests? ---
**Author:** ![Sublight](https://avatars.discourse-cdn.com/v4/letter/s/439d5e/32.png) [@Sublight](https://boards.straightdope.com/u/Sublight)\ **Post date:** [August 6, 2006, 3:28pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/2 "2006-08-06T15:28:01Z")
I don’t know how it’s synthesized, but Landis was caught not because the testosterone was recognized as not his own, but because his hormone ratios were way out of balance, indicating that something had been added artificially. The testosterone itself may have been natural. In this case, the acceptable ratio of testosterone to somethingelse-erone was 4:1 or less. Landis had a ratio of 11:1. ---
**Author:** ![mnemosyne](https://avatars.discourse-cdn.com/v4/letter/m/c4cdca/32.png) [@mnemosyne](https://boards.straightdope.com/u/mnemosyne)\ **Post date:** [August 6, 2006, 3:52pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/3 "2006-08-06T15:52:21Z")
IIRC from a long-ago biochemistry course, synthetic hormones are largely made from plant or bacterial extracts. By breaking down the plant (for example) you can obtain a class of molecules called sterols, which all share a common core structure. Variants in side chains of these molecules lead to the differences between cholesterol, testosterone, progesterone, estrogen, etc. The chemical reactions to change the side chains are relatively trivial in the lab. In the body, all the hormones are made from cholesterol through various pathways. In the case of testosterone doping, the test searches for carbon isotope ratios (that is, the amount of C13 and C14 in the molecule - most carbon atoms are C12). If the drug was derived from another source, such as a plant, then because of how it was nourished and such it would have a different isotope ratio than the person taking it. This article explains it fairly well: [Testosterone, Carbon Isotopes, and Floyd Landis – Corante](http://pipeline.corante.com/archives/2006/08/01/testosterone_carbon_isotopes_and_floyd_landis.php) ---
**Author:** ![Frylock](https://avatars.discourse-cdn.com/v4/letter/f/ce7236/32.png) [@Frylock](https://boards.straightdope.com/u/Frylock)\ **Post date:** [August 6, 2006, 4:14pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/4 "2006-08-06T16:14:52Z")
> [@Sublight](#): > > I don’t know how it’s synthesized, but Landis was caught not because the testosterone was recognized as not his own, but because his hormone ratios were way out of balance, indicating that something had been added artificially. The testosterone itself may have been natural. > > In this case, the acceptable ratio of testosterone to somethingelse-erone was 4:1 or less. Landis had a ratio of 11:1. My wife and I saw a story on the news last night which we both immediately (i.e. prior to any discussion with each other) took to indicate both that there was too much testosterone and that some of it was synthetic. -FrL- ---
**Author:** ![don\_t\_ask](https://avatars.discourse-cdn.com/v4/letter/d/e68b1a/32.png) [@don\_t\_ask](https://boards.straightdope.com/u/don_t_ask)\ **Post date:** [August 6, 2006, 4:23pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/5 "2006-08-06T16:23:28Z")
> [@Sublight](#): > > I don’t know how it’s synthesized, but Landis was caught not because the testosterone was recognized as not his own, but because his hormone ratios were way out of balance, indicating that something had been added artificially. The testosterone itself may have been natural. > > In this case, the acceptable ratio of testosterone to somethingelse-erone was 4:1 or less. Landis had a ratio of 11:1. Landis’s problem is that the testing can distinguish natural testosterone from synthetic testosterone. His story is apparently all lies because the testosterone in his system was not naturally produced. ---
**Author:** ![don\_t\_ask](https://avatars.discourse-cdn.com/v4/letter/d/e68b1a/32.png) [@don\_t\_ask](https://boards.straightdope.com/u/don_t_ask)\ **Post date:** [August 6, 2006, 4:26pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/6 "2006-08-06T16:26:31Z")
Sorry [link](http://msn.foxsports.com/cycling/story/5834528) ---
**Author:** ![solkoe](https://avatars.discourse-cdn.com/v4/letter/s/919ad9/32.png) [@solkoe](https://boards.straightdope.com/u/solkoe)\ **Post date:** [August 6, 2006, 4:43pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/7 "2006-08-06T16:43:27Z")
I still would like to know if it is possible to extract testosterone from another person, use it in competition and not be caught by drug tests? ---
**Author:** ![ultrafilter](https://avatars.discourse-cdn.com/v4/letter/u/3d9bf3/32.png) [@ultrafilter](https://boards.straightdope.com/u/ultrafilter)\ **Post date:** [August 6, 2006, 4:45pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/8 "2006-08-06T16:45:56Z")
> [@solkoe](#): > > I still would like to know if it is possible to extract testosterone from another person, use it in competition and not be caught by drug tests? You could still get caught by having testosterone levels that are far too high. ---
**Author:** ![solkoe](https://avatars.discourse-cdn.com/v4/letter/s/919ad9/32.png) [@solkoe](https://boards.straightdope.com/u/solkoe)\ **Post date:** [August 6, 2006, 9:18pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/9 "2006-08-06T21:18:10Z")
Thanks for your responses, I still would like to know if it is possible to extract testosterone from another person, use it in competition and not be caught by drug tests? ---
**Author:** ![John\_Mace](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/john_mace/32/185_2.png) [@John\_Mace](https://boards.straightdope.com/u/John_Mace)\ **Post date:** [August 6, 2006, 9:27pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/10 "2006-08-06T21:27:14Z")
Maybe you could extract it from many people, but I doubt you’d get enough from just one person w/o killing him. Landis’ testosterone levels were many times higher than normal, so you’d have to drain the equivlant of several people’s entire supply of blood to hope to get enough. Then you’d need a purification process that could extract only the testosterone. BTW, the wiki article on [testosterone](http://en.wikipedia.org/wiki/Testosterone) discusses its synthesis. > [@](#): > > Testosterone is synthesized from pregnenolone, which is the precursor of all steroid hormones and a derivative of cholesterol. ---
**Author:** ![Harmonious\_Discord](https://avatars.discourse-cdn.com/v4/letter/h/74df32/32.png) [@Harmonious\_Discord](https://boards.straightdope.com/u/Harmonious_Discord)\ **Post date:** [August 6, 2006, 10:00pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/11 "2006-08-06T22:00:52Z")
There actualy was a star trek movie on this. The people were on a new planet and the men didn’t make enough testosterone, to trigger the sexual developement of male adolesents. The slaves were killed to feed the pituitory gland to the elites childern. They introduced the synthetic testosterone to stop the practice. I believe that pituitory extraction from cadavers was the original source for the hormone. ---
**Author:** ![Paul\_in\_Qatar](https://avatars.discourse-cdn.com/v4/letter/p/ccd318/32.png) [@Paul\_in\_Qatar](https://boards.straightdope.com/u/Paul_in_Qatar)\ **Post date:** [August 7, 2006, 2:30am UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/12 "2006-08-07T02:30:17Z")
I don’t know. I just check the labeling of my German-made testosterone (‘in an oily base’) and I note it is not labeled ‘From recombinant DNA.’ My brother’s insulin is labeled that way for whatever reason. Does that help? ---
**Author:** ![threemae](https://avatars.discourse-cdn.com/v4/letter/t/5f9b8f/32.png) [@threemae](https://boards.straightdope.com/u/threemae)\ **Post date:** [August 7, 2006, 3:35am UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/13 "2006-08-07T03:35:43Z")
> [@John Mace](#): > > Landis’ testosterone levels were many times higher than normal, so you’d have to drain the equivlant of several people’s entire supply of blood to hope to get enough. As a slight nit-pick, we don’t know how high his testosterone level actually was, simply that his ratio of testosterone to epitestosterone was an 11:1. Either the numberator or the denominator could have changed to produce that result. Also, the mass spec data seems to make a hard rap to beat although no one has yet leaked any quantification of how this test actually supposedly broke down and how significant of finding it was. He have a greater idea of the significance of the testosterone:epitestosterone test because it’s been leaked that the ratio was an 11:1. ---
**Author:** ![Rusalka](https://avatars.discourse-cdn.com/v4/letter/r/ecd19e/32.png) [@Rusalka](https://boards.straightdope.com/u/Rusalka)\ **Post date:** [August 7, 2006, 3:40am UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/14 "2006-08-07T03:40:48Z")
How is the synthetic testosterone administered? Is it possible someone slipped him some in his food without him knowing about it? I guess this isn’t possible if it requires an injection. The whole situation sounds strange, many news reports I’ve read say that the testosterone is something you take weeks before, and that taking it the night before doesn’t give you much benefit. Why would Landis be so stupid? ---
**Author:** ![threemae](https://avatars.discourse-cdn.com/v4/letter/t/5f9b8f/32.png) [@threemae](https://boards.straightdope.com/u/threemae)\ **Post date:** [August 7, 2006, 3:53am UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/15 "2006-08-07T03:53:24Z")
> [@John Mace](#): > > BTW, the wiki article on [testosterone](http://en.wikipedia.org/wiki/Testosterone) discusses its synthesis. I believe that’s referring to synthesis in the body, not artificial synthesis by organic chemists. I think that William Johnson from Stanford actually produced industrial-scale synthesis of testosterone in the 40’s and 50’s and I don’t think it involves pregnenolone, etc. “In a previous paper,2 we described the total synthesis of testosterone (I) in ten steps from the readily accessible tetracyclic ketone 11. The first step involved conversion to the ketal I11 in order to protect the sensitive ring A a,@-unsaturated ketone system which, in the last stage of the synthesis, was finally regenerated by hydrolysis. While this method of preserving the unsaturated ketone system provides a relatively short pathway to the desired objective, it suffers in that it limits the types of operations that can be performed on the intermediates. Thus mild acidic solvolytic conditions must be avoided, and all reactions that attack olefinic bonds, e.g., hydrogenation and ozonization, must be performed selectively so as to minimize reaction with the double bond in ring B of the ketal 111. Another approach to the objective involves removal of the a,@-unsaturatedk etone system of I by reduction of the X/B cis-saturated alcohol (cj‘. formula IV) then, at an appropriate later state, reintroduction of the unsaturated ketone residue by oxidation, bromination and dehydrobromination. Although less appealing intellectually, this more pedestrian approach has certain practical advan-” From: [http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1960/82/i13/f-pdf/f\_ja01498a043.pdf?sessid=6006l3](http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1960/82/i13/f-pdf/f_ja01498a043.pdf?sessid=6006l3) It’s a 1960 article in the Journal of the American Chemical Society. ---
**Author:** ![Cardinal](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/cardinal/32/4000_2.png) [@Cardinal](https://boards.straightdope.com/u/Cardinal)\ **Post date:** [August 7, 2006, 4:03am UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/16 "2006-08-07T04:03:54Z")
ESPN radio says that testosterone isn’t the kind of thing that would help for one race. I wonder if there isn’t something either weird with Landis’ levels of the second hormone, or if he could have lowered the second one with some other treatment, legal or illegal. ---
**Author:** ![Princhester](https://avatars.discourse-cdn.com/v4/letter/p/3e96dc/32.png) [@Princhester](https://boards.straightdope.com/u/Princhester)\ **Post date:** [August 7, 2006, 4:10am UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/17 "2006-08-07T04:10:39Z")
> [@Rusalka](#): > > How is the synthetic testosterone administered? Is it possible someone slipped him some in his food without him knowing about it? I guess this isn’t possible if it requires an injection. > > The whole situation sounds strange, many news reports I’ve read say that the testosterone is something you take weeks before, and that taking it the night before doesn’t give you much benefit. > > Why would Landis be so stupid? [www.cyclingnews.com - the world centre of cycling](http://www.cyclingnews.com/news.php?id=news/2006/jul06/jul07news3), last article on the page. Note that this is an article written _before_ the Landis scandal broke, ie it’s not someone being wise after the event. Note also that _recovering faster_ was precisely what he needed to do, on the occasion he is supposed to have doped. ---
**Author:** ![R.P.McMurphy](https://avatars.discourse-cdn.com/v4/letter/r/7993a0/32.png) [@R.P.McMurphy](https://boards.straightdope.com/u/R.P.McMurphy)\ **Post date:** [August 7, 2006, 12:10pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/18 "2006-08-07T12:10:48Z")
> [@Rusalka](#): > > How is the synthetic testosterone administered? Is it possible someone slipped him some in his food without him knowing about it? I guess this isn’t possible if it requires an injection. > > The whole situation sounds strange, many news reports I’ve read say that the testosterone is something you take weeks before, and that taking it the night before doesn’t give you much benefit. > > Why would Landis be so stupid? Here is probably the most common method of administering testesterone: [Androgel](http://www.androgel.com/) The track star that was recently busted was trying to say that he got sabataged by a massage therapist. Possible but not likely. Something about the Landis story doesn’t seem right. What were the test results after his previous stage wins? Testesterone is far more effective for building strength over a long period of time than as a quick fix. If you need to become a one day wonder then amphetamines or blood doping would be much more effective. Also, is/was the second place finisher equally tested? ---
**Author:** ![Squink](https://avatars.discourse-cdn.com/v4/letter/s/b5e925/32.png) [@Squink](https://boards.straightdope.com/u/Squink)\ **Post date:** [August 7, 2006, 12:29pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/19 "2006-08-07T12:29:47Z")
> [@Spartydog](#): > > Something about the Landis story doesn’t seem right. What were the test results after his previous stage wins? Testesterone is far more effective for building strength over a long period of time than as a quick fix. True, but how quickly does the stuff turn you into an aggressive madman? ---
**Author:** ![R.P.McMurphy](https://avatars.discourse-cdn.com/v4/letter/r/7993a0/32.png) [@R.P.McMurphy](https://boards.straightdope.com/u/R.P.McMurphy)\ **Post date:** [August 7, 2006, 1:31pm UTC](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561/20 "2006-08-07T13:31:30Z")
> [@Squink](#): > > True, but how quickly does the stuff turn you into an aggressive madman? If he had enough in him to become an aggessive madman, his ratio would have been far greater than 11-1. Body builders have had ratios of 100-1. While Landis’ ratio was high, it was not outrageous. [Next page](https://boards.straightdope.com/t/question-about-synthetic-testosterone/367561.md?page=2)