Wednesday, October 23, 2013

Helper, Chiral Destroyer

    Thalidomide, or Contergan, was invented by the German pharmaceutical company Grunenthal which helped women with insomnia, coughs, colds, and headaches. It was said to be the cure for morning sickness, a spell of nausea and sickness that strikes more than half of pregnant women experience in the early hours of the morning (and tends to dissipate throughout the day).
    This chiral molecule exploded in popularity in the mid 1900s as it actually worked. It did not take long for birth defects to be noticed in correlation with the drug, however. The drug ended up causing abnormalities in children often times deforming their extremities.
    THE CRAZY PART- (R)-thalidomide has absolutely no influence on the growth and development of an unborn fetus. In fact, it is proven to successfully alleviate said anxiety, insomnia, gastritis, and tension of pregnant women, and do nothing but that. (S), on the other hand, binds to the protein cereblon, a protein necessary in limb formation, and inhibits it. This two molecules are racemic, which is why we haven't tampered too greatly with the development of the (R) only medicine.

Pictured: (R) above (S). Stereochemistry of relevant chiral center drawn.

Thanks to Wikipedia and


  1. Wow!! I wrote about Thalidomide also. And the even crazier part is that they still use this drug today to treat numerous disease even though it caused so many problems.

  2. Its interesting that a drug that caused so many problems is still used today. It's also cool how R has not influence on growth but yet S does.