This news item was created by students Nick Vernetti, Erica Moore, Kristopher Chilcutt, Don Yap, and Amanda Kline as part of their Chemistry 212 Collaborative Group Projects in WS00 under the guidance of Prof. Rainer Glaser.

Glaser's "Chemistry is in the News"
To Accompany Wade Organic Chemistry 4/e.
Chapter 25. Lipids.

For each of the following questions, please refer to the following article:

by Ulysses Torassa (San Francisco Examiner, 2000)

Editorial Comments

BigMac. Slammin' Sammy. These two baseball icons captivated a nation with their classic homerun race in the summer of 1998. During that season, Sammy Sosa and Mark McGwire eclipsed and then went on to bury Roger Maris' single season record of 61 homers. McGwire blasted an unprecedented 70 big ones, while Sosa finished close behind with an impressive 66. Sosa's charming, "happy-go-lucky" approach to the contest and McGwire's Paul Bunyan-esque stature gave the duo instant appeal. Both men were active community leaders; Sosa gave financial aid to his Dominican homeland, and McGwire was active in his foundation for abused children.

As always, the media made its effort to spoil the mood and put a spin on the saga by tainting the image of the favorite to win the homerun crown, Mark McGwire. Late during that magical summer, a reporter found a bottle of supplements containing androstenedione in McGwire's locker. "Andro," as it is often referred to by body builders, is a workout supplement that theoretically helps boost muscle protein production and strength. Androstenedione is banned in other major sports like basketball and football, and Major League Baseball is beginning to look into their policy after the McGwire discovery. Looking logically at the problem, most could see that big muscles don't give you the hand-eye coordination and talent to hit a 94 mph fastball 500 feet, but the question was still being raised as to whether or not "andro" was responsible for Mac's surge to 70.

Androstenedione is a precursor to testosterone, a hormone that among other things promotes muscle growth. The [East] German Olympic team began using it in the 1970's to improve their swimming team's performance. Since then, many web based companies such as,, and push this product to weightlifters as a way to improve the efficiency of workouts and "bulk up." Review the article on that acknowledges this theory, and puts it to the test. Many other medical websites such as and a study done in 1998 say that it is too early in the game to know exactly what long term effects androstenedione supplements will have on the user. Most of these preliminary studies have presented evidence that androstenedione supplements will do about everything but what it is designed to do. Instead of rippling muscles scientists have seen everything from acne to high cholesterol to heart disease to elevated estrogen levels (... increased cancer risk?). Even the development of male breasts has been named in the broad spectrum of possible consequences for altering the body's natural androstenedione levels.

Androstenedione falls into the category of simple lipids known as steroids. If you take a look at chemfinder's image of androstenedione you will see a fairly straightforward tetracyclic molecule. The molecule contains two cyclohexanes linked together. Linked to one of these cyclic units is a cyclohexeneone and the other cyclohexane has a cyclopentanone attached. The two carbonyl groups of these ketones are on carbon 3 and carbon 17, while two methyl groups stick out from carbon 18 and 19. The molecule's double bond is found on carbon 4 (see book's nomenclature).

Look at chemfinder's image of testosterone. Examine the structure to see how it differs from its androstenedione precursor, and you will see a very clear relationship. The body uses 17-beta-hydroxy-steroid oxidoreductase to make this conversion. This is the basis of the theory behind using androstenedione to give you more testosterone, but in practice it is not that simple. Androstenedione is also a precursor for forming estrogen, a hormone responsible for feminine characteristics. Studies indicate that this pathway is what might create some undesired side effects, and would explain some of the experiences guys have had with this pill who thought it would help them "bulk up" when actually it helped them ... ehhh hem ..."fill out."

Pertinent Text References
Chapter 25. Lipids.
In particular the discussion of steroids in Wade 4/e pg. 1173-1175.


Question 1: According to "Study Raises Testosterone Levels," if a young Mark McGwire took 100mg of "andro" everyday after school what effects could it have on his body?

Answer: Higher estrogen levels- possible breast formation. No increase in testosterone!

Question 2: What stance does the article seem to take on the controversy over the use of androstenedione?

Answer: The article takes a cautious approach to its use because they are still early in the testing stage, they found no beneficial results at all, and had some definite evidence of dangerous side effects.

Question 3: Check out chapter 25 on steroids. What is androstane and how is it different from androstenedione? Describe the conformation they are normally found in. Why is an enzyme needed in making testosterone from androstenedione?

Answer: Androstane is the simplest steroid on which other more complex steroids like androstenedione, testosterone, and estrodiol are based. Androstenedione is androstane except that it has two carbonyl groups on carbon 3 and carbon 17 of the molecule. Androstenedione also contains a double bond at carbon 4 that is not found in androstane. The conformation is normally planer (trans) for steroid systems. An enzyme is needed in order to overcome the activation energy barrier when reducing carbon 17Ős carbonyl group to the hydroxyl group found in testosterone.

Question 4: Do a search for androstenedione on the web and look at all the companies who hype the prospect of boosting testosterone levels using products like "andro." What techniques do they use to make an athlete or prospective buyer believe this is a good thing? Compare the information of these supposed experts to the findings in the links above to actual scientists who say the effects still aren't clear. Do you see a credibility problem here?

Answer: These companies typically attempt to use excessive technical terminology and statistics to overwhelm and convince the buyer of the company's knowledge of the product. These websites all seem to have "andro" completely figured out and promise that the testosterone boost will yield a substantial increase in muscle production; yet, most true studies haven't found any evidence that this occurs and still have more questions than they do answers. If a buyer is shielded from these truths and blindly takes the claims of advertisements as fact, then the proven risks won't be properly examined.

Question 5: McGwire was quoted as saying he used "andro" because it was a "natural" supplement. Do you agree with this philosophy? Explore this reasoning for the use of any type of drug or foreign substance.