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On This Day

2013 — In the Boston Marathon, Joan Benoit Samuelson ’79 breaks the marathon world record for her age group (women 50-55) by more than two minutes, and beats her goal of coming within 30 minutes of her winning time 30 years ago. The race was marred by a terrorist bombing at hour 4:09. Two blasts on Boylston Street within 12 seconds claimed the lives of three people and injured more than 180, many grievously.

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Michael Danahy: ‘Better Living Through Chemistry?’

Michael Danahy

President Mills, Dean Judd, members of the Bowdoin faculty and staff, family and friends of our honorees, it is a great privilege to speak to you tonight. Let me be one of the first people to congratulate our honorees on their well-deserved awards. You have reached the pinnacles of your respective departments and for that we all congratulate you.

I realize that I am one of the final impediments between you and your awards, so I’ll try to be brief. But, what to talk about? What words of encouragement, enlightenment, or even warning can I impart? I make my living teaching a class that is one of the more reviled on a college campus: organic chemistry. I was recently at an accepted students reception and even they, 18-year-old seniors in high school, cringed when I told them I taught organic chemistry! So, what makes me excited about organic? Why do I love teaching it? Am I merely a sadist?

First and foremost it’s the chemistry. You get to make and isolate cool molecules! Many students have told me that learning organic chemistry is probably the closest they will come to the “Potions” class featured in the Harry Potter book series. You really feel like a wizard mixing chemicals together in intricate glassware, refluxing them for the right amount of time, commanding them to crystallize, and isolating new compounds.

But apart from the chemistry, organic has a very storied history and this history is just as interesting as the chemistry itself. The history of organic chemistry demonstrates the power of serendipity in discovery. New molecules coming from unexpected places! Organic also teaches us that in being modern-day wizards, we must ensure that our work furthers the “common good” and fosters “better living though chemistry.”

Organic chemistry began as a very utilitarian field. William Perkin of Britain is considered by many to be a father of organic chemistry, and he was working on a very utilitarian problem in 1856: treating malaria. Let’s think about Britain of the 1850’s. You’ve got a global Empire, located in tropical locations. Diseases such as malaria are rampant. No worries, nature has a tree, the cinchona tree, indigenous to South America, which contains the anti-malarial molecule quinine. A beautiful molecule, I might add. I recommend up its structure. Nature really makes elegant things, especially on the molecular level. OK, you’ve got quinine, so long as you keep your colonists supplied with tree bark, no more malaria. The problem is that South American countries, wanting a monopoly on quinine, banned the export of cinchona saplings; the British were beholden to these nations for a desperately needed drug. Perkin comes along and decides that he is going to synthesize quinine in the lab. He mixes his chemicals together, adds a little this, a little that and boom…black tar at the bottom of the flask. Not quinine. Like any good scientist, he begins to wash his glassware and start over. But wait! The alcohol he used to clean the black tar from his flask turned a beautiful purple color as it went down the drain! Perkin stumbled across the first synthetic dye (mauvine). As an associate of Perkin told him, “if your discovery does not make the goods too expensive it is decidedly one of the most valuable that has come out for a very long time.” Before Perkin, nature was the source of many cloth dyes, and clothes for most people were pretty drab. Perkin and synthetic dyes literally changed the palette of colors garment makers could use, and many (if not all) of the colored clothes in this audience today are offshoots of Perkin’s serendipitous discovery.

Serendipity in organic chemistry is not limited to the very beginnings of the field. Let’s fast-forward to 1985. Chemists at Pfizer were investigating compounds that could be useful in treating angina and high blood pressure. They began looking at molecules that dilated cardiac blood vessels. The compounds they studied were non-selective drugs and lead to a variety of side effects. But, after three years and 1600 compounds screened, they finally found a compound that was a specific dilator of cardiac blood vessels in vitro, called UK-92480. They made a salt of the molecule in increase its water solubility and named the molecule sildenafil citrate.

Pfizer began clinical trials of sildenafil citrate in 1992, and they were a flop. Although the compound was effective in vitro, it was an ineffective cardiac drug in vivo. Pfizer decided to stop the study; 7 years of research for nothing. But, to Pfizer’s surprise, when clinicians came to collect the unused tablets, the subjects refused to let them go. They found that male subjects of the study “suffered” an “unexpected side effect” of sildenafil citrate: improved erections. In fact, of those on high doses of the drug, 88% reported improvements. Pfizer then began clinical trials of sildenafil citrate as an erectile dysfunction drug and again 85% of subjects reported improved erections. In 1996 Pfizer patented the drug and gave it the trade name Viagra. It came to the US market in 1998 and in 2008 was a two-billion-dollar a year drug for Pfizer. A nice return on a serendipitous discovery.

Many of you have had discoveries like Perkin’s mauvine or Pfizer’s Viagra in your careers at Bowdoin. You perhaps came to Bowdoin intending on majoring in biology and becoming a physician. But along the way, an exciting class or professor or research experience made you discover a path you did not intend. Or, like Perkin a “failed experiment” in one academic field pushed you into another. Now, you’ve found your passion as an English major, or a mathematician, or perhaps you’re still a biology major but are now interested in ecology and want to go to graduate school and not medical school. For those of you who have not had a Perkin or Viagra-like moment at Bowdoin, be open to it. As Pasteur famously said “chance favors the prepared mind.” Be open to new ideas, new insight that by chance comes across your path. Many times the serendipitous discoveries, whether in academia or in general, are the most life changing.

Back to chemistry. Soon after Perkin’s serendipitous discovery of mauveine, many people opened dyeworks. The dye industry of 1850’s Germany was the equivalent to Silicon Valley of the 1990’s with hundreds of people starting businesses to make their fortunes. One of these fortune seekers was Friedrich Bayer who in 1863 started Farbenfabriken Bayer or the Bayer Color Factory. Every boom has its bust and by the 1880’s the dye industry was beginning to wane; Bayer had to change the focus of his company or face going under. Bayer transformed his “Color Factory” into the pharmaceutical company we know today. Around this time, physicians were becoming aware of the adverse effects of fever on the human body and antipyretic drugs were the rage. It had been known for about 3000 years that the bark of the willow tree was effective in treating rheumatism and was an analgesic. By the late 1700’s the active ingredient of the bark, sodium salicylate, was being marketed as an analgesic and a treatment for fever associated with malaria. The problem with sodium salicylate was that it tasted horribly and was extremely irritating to the stomach. According to the journal Archiv fur die Gesamte Physiologie, “the use of sodium salicylate would be definitely much more popular if it would not provoke strong rejection by its disgusting sweet taste which can be corrected only to some extent.” A chemist working for Bayer, Felix Hoffmann was playing with sodium salycilate and found by transforming (or acetylating) the molecule, the new compound was effective in treating rheumatism, but was devoid of the horrible gastrointestinal issues. Hoffman had come up with a synthesis of acetylsalicylic acid or aspirin. Since its introduction by Bayer in 1899, aspirin has been wildly successful. The Guinness Book of World Records has listed aspirin as the most commercially successful of drugs. Although originally marketed as a drug to treat fevers and alleviate pain, aspirin has been found effective in reducing cardiovascular disease, and there is mounting evidence that a daily aspirin regiment can reduce the risk of cancer. It is truly a wonder drug, one that has no doubt advanced the “common good.” Not bad for a drug that was discovered over 110 years ago and is derived from willow bark!

But, not all is rosy for Felix Hoffmann and Bayer. For while Hoffman was acetylating salicylates, synthesizing aspirin, he was also trying to acetylate other drug compounds in hopes of making them “better”. But I’m getting ahead of myself, we need to back up and talk about narcotics. Since antiquity, the opium poppy had been used as a pain reliever and sleep inducer. In 1810, a German chemist first isolated the active ingredient of opium, and named it morphine. Morphine was introduced to the US in the 1850’s and its ability to alleviate severe pain was nothing short of miraculous. Morphine use really took off in this country during the Civil War, alleviating pain for wounded soldiers, but something else took off: morphine addiction. In response to the huge spike in global morphine addiction, physicians began to curtail its use and looked for non-addictive alternatives. Enter our friend Felix Hoffman. In 1897 he acetylated the morphine molecule, synthesizing diacetylmorphine in a fashion very similar to his synthesis of aspirin. Hoffman’s boss at Bayer, Heinrich Dresser, thought they had something. Dresser, and others at the time, had the unfounded opinion that acetylating a molecule reduced all its deleterious effects (it worked with aspirin!), and by acetylating morphine, it would be rendered non-addictive. Dresser carried out tests of diacetylmorphine on Bayer factory workers, and they described the drug as making them feel “heroic”, thus leading to Bayer’s marketing of the drug heroin, the “non-addictive” morphine. Well, we all know the rest of the story. Heroin, and other synthetic morphines such as oxycodone and hydrocodone are some of the most addictive narcotics. In fact, the state of Maine tops the nation in the percentage of its population seeking treatment for opiate addiction.

The story of aspirin and heroin start along the same path: both of these drugs were derived from natural products and both were synthesized using the same organic reaction of “acetylation”. They both “changed the world”, but where they diverged is in their application; they “changed the world” in very different ways. We cannot deny the huge impact aspirin has had in furthering the “common good”. Likewise, the “common good” has no doubt been set back by the huge societal crisis introduced by heroin. Even great discoveries can have unintended consequences. At Bowdoin, we strive to increase your knowledge across various fields. As you continue through Bowdoin and one-day leave us, remember that what you do with your intellectual discoveries is in your hands. Please strive to apply your knowledge in a positive way and help further the “common good.” By furthering the “common good”, we can all experience better living through a path that you helped forge.

Once again, congratulations on all your achievements! Thank you.