Aspirin Intrigue

    What is the difference between fake aspirin and real aspirin? If they are chemically the same, that is, acetylsalicylic acid (ASA), then what is the fuss? Are they both indeed ASA? A bit of manufacturing history may clear up this question.

    Click to see a phenacetin molecule in 
3-D!
    phenacetin
    Bayer Company, the German chemical giant, had the great good fortune to get out of the dye-making business and into the pharmaceuticals business very early. Bayer called its first pharmaceutical product, created wholecloth from waste products, acetophenetidin. Hoping to promote this pain reliever under its brand name rather than its chemical or generic name, its creators called this new drug Phenacetin. This new pharmaceutical marked the beginning of the modern drug industry—for the first time, a drug had been conceived, developed, tested, and marketed by a private company. Bayer looked forward to enormous profits from this and future drug products it might create.

    Click to see
a heroin molecule in 3-D!
    Bayer's next addition to the Pharmacopoeia was, of all things, heroin! Ironically, heroin was synthesized by none other than Felix Hoffmann. Doctors in the late 1800s were very worried about their patients' growing addiction to the painkiller morphine. Bayer rediscovered a morphine derivative, diacetylmorphine, that made their guinea-pig workers feel "heroic" and began to market this "nonaddictive" substitute for morphine under the brand name "heroin." Doctors even prescribed heroin to cure babies' colic!

    Meanwhile, ASA languished on Bayer's shelves. In ancient times, as you know from reading other parts of this Web site, it had been discovered that the salicylic acid (SA) from white willow bark had analgesic and anti-inflammatory properties. SA was pretty hard on the digestive system, however, so a more gentle form was sought. Back in 1853 a French chemist named Charles F. Gerhardt had synthesized crude ASA, the milder form, and Karl J. Kraut, a German, succeeded in synthesizing a purer form sixteen years later. So Bayer, in the person of Felix Hoffmann, was a Johnny-come-lately to the scene when, in 1897, he described his own success in producing ASA. Although Hoffmann, and his boss, Arthur Eichengrün, knew of the earlier syntheses of ASA, this did not deter them from passing it on to their boss, Heinrich Dreser, who was singularly unimpressed. He rejected ASA out of hand under the mistaken notion, gleaned mostly from hearsay, that ASA made the heart weaker. How ironic that almost a century later, in 1988, a study in the Journal of the American Medical Association would pronounce ASA a marvelous heart-attack preventive.

    Due to Eichengrün's persistence, Dreser finally agreed to pharmacological testing of ASA, and after the glowing reports rolled in, he took credit for the discovery himself, failing to mention either Eichengrün or Hoffmann in his scientific papers. Bayer coined the name Aspirin for its new product, and it was off to the races with respect to sales and profits.

    Israeli Bayer aspirin with crossed name logo
    Bayer® aspirin packaged for sale in
    Israel, featuring the crossed-name
    logo.
    Bayer wanted to corner the large potential aspirin market in the United States and at the same time avoid the country's high import duties. In 1903, it began a large aspirin plant in Rensselaer, New York. Holding the U.S. patent on aspirin and its trade name as well, Bayer was well-positioned to capture the minds and pocketbooks of a large portion of the American citizenry. But Bayer could not foresee World War I and that its U.S. assets would be seized by the U.S. government and sold at auction. The highest bidder, Sterling Drug Company, bought not only Bayer's assets, but also its rights to its name and to the famous trademark of BAYER crossed vertically with BAYER at the Y.

    sodium acetate
    sodium acetate 
    Even before the breakup of Bayer, contraband formulators and smugglers had been making sure that cheaper, albeit illegal, aspirin graced the shelves of the drugstores of North and South America. Many of these products, the fake aspirin alluded to above, were simply cornstarch, or some aspirin mixed with cornstarch or any other white, powdery substance that was cheap and available. In some instances, the formulators simply mixed SA with some sodium acetate salt, but left it chemically unreacted.

    If you were a government sleuth at the time, how could you distinguish fake aspirin from real aspirin? Could you design an experiment that would tell you if you had a non-ASA product on your hands or ASA mixed with other ingredients? You can do just that in the activity Real or Phony?

      Next: A Festival of Analgesics

    For more information, at other Web Sites...

      3 Fake Drugs Are Found in Pharmacies — from the New York Times, 5 June 2001.

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    Image credit

      Bayer® aspirin packaged for sale in Israel: Courtesy Marvin Samson Center for the History of Pharmacy, University of the Sciences in Philadelphia.


    Copyright ©2001 The Chemical Heritage Foundation