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6 days ago on May 21, 2012 at 07:23pm
16KCl3 + 3P4S3 → 16 KCl + 9SO2
This molecule is called Thalidomide.
It is a sedative drug introduced in the late 1950s that was used to treat morning sickness. It was sold from 1957 until 1961, when it was withdrawn after being found to be a cause of birth defects.
In the late 1950s and early 1960s, more than 10,000 children in 46 countries were born with deformities, such as phocomelia, as a consequence of Thalidomide use. It is not known exactly how many worldwide victims of the drug there have been, although estimates range from 10,000 to 20,000.
Part of the reason why thalidomide is teratogenic is now known. The molecule shown above is (S)-thalidomide. It has a non-superimposable mirror-image molecule (an enantiomer) called (R)-thalidomide. In the drug used to treat morning sickness, the two stereoisomers were racemic - that is, the two molecules that are mirror images of each other were mixed in equal amounts. The (S) enantiomer causes birth defects by mechanisms that are not entirely understood, though many possible pathways have been proposed.
But even if only (R)-thalidomide was used in the drug, it would not have prevented the effects of the molecule on fetuses, since either enantiomer can convert into its mirror image. The only way to prevent birth defects was to stop the use of the drug altogether.
Thanks for posting this - “chirality” is truly fascinating; it’s extremely important in most of the top 100 pharmaceutical compounds (by revenue) and drug discovery in general. I’ve also always wondered what the first chiral molecule ever was. Will we ever know?
