This news item was created by students Blake Borello, Dave Britt, Chris Plumpe and Jennifer Weeks as part of their Chemistry 216 Collaborative Group Activities in FS01 under the guidance of Prof. Rainer Glaser.

Glaser's "Chemistry is in the News"

By Karen S. Peterson, USA TODAY, March 21, 2001.

Editorial Comments

Millions of men around the world suffer from erectile dysfunction, also known as impotence. Viagra is a drug that helps produce and maintain erections for four out of five men. Viagra used Bob Dole as a national spokesperson, which was part of their successful ad campaign. Now, three years after viagra was introduced, more than seven million men have improved their response to sexual stimulation and are living much happier lives. Many people find the subject of Viagra humorous, while it is a very serious issue for others.

Recently, as is the case with many other drugs, Viagra too is falling into the wrong people's hands and is being abused. Ecstasy, amphetamines, cocaine, alcohol, marijuana, and other party drugs are now joined by the new member Viagra. Unknown to most, the combination of Viagra with these other party drugs can be harmful and at times, deadly. Amyl nitrate, also known as "poppers" poses the greatest threat to one's health. Both amyl nitrate and Viagra dilate blood vessels and increases blood flow, resulting in the decrease of blood pressure. This can lead to stroke or heart attack.

When a man is sexually stimulated cyclic guanosine monophosphate (cGMP) causes blood flow to the penis resulting in the formation of an erection. Once a man is no longer sexually stimulated a compound is released causing the penis to become flaccid. Viagra inhibits the release of this compound prolonging an erection.

Viagra is a compound made up of a carboxylic acid and a base forming a salt. Once ingested, the base and the carboxylic acid break apart. The base is the part of the compound that is used to treat impotence. The main function of the carboxylic acid is simply the formation of the salt. The drug is delivered more easily if in the form of a salt.

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For more general information, go to:

To learn technical information on how Viagra works, go to:

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Pertinent Text References

Chapter 20: Carboxylic Acids


Question 1: Use chemfinder to find out the structure, formula, formal name, and exactly how many carboxyl groups are contained in Viagra? Refer to chapter 20-1 in Wade, if you have forgotten what a carboxyl group is.

Answer: Online. The formal name is Sildenafil Citrate. There are three carboxyl groups.

Question 2: The two parts of Viagra combine to form a salt. Once in the body, the top structure breaks off from the bottom structure to produce the effects. Identify which structure is the base and which is the acid.

Answer: The heterocyclic system is the base.

Question 3: NO is the molecule that causes the erection in men, and cyclic guanosine monophosphate (cGMP) allows the inflow of blood to the penis. There is another molecule that inhibits the cGMP. What is this the name of this molecule?

Answer: The name of this molecule is phospodiesterase type-5(PDE5).

Question 4: Give an example of how a carboxylic acid can be made. Refer to section 20-8 Wade.

Answer: Oxidation of primary alcohol via aldehyde to carboxyliuc acid.

Question 5: Knowing that Viagra can be used to treat impotence, erectile dysfunction, and some heart problems, do the benefits outweigh the risks that are presented by those people who are using the drug for recreational purposes along with other drugs which presents great health risks? What should the government do to control or discourage the improper use of viagra?