Chirality of Thalidomide

Kurt Giles (
Wed, 31 Jan 1996 13:03:25 +0200

An example of chirality that I was given as an undergraduate (and one that I
unwittingly passed on to my students) was that one enantiomer of thalidomide
was a useful drug for the prevention of morning sickness and safe, the other
was highly teratogenic. In the '60's thalidomide was administered as the
racemate, hence the disasterous results.

However, I read recently in 'Chemistry in Britain' (the magazine of the Royal
Society of Chemistry) that it has long been known that both enantiomers are
teratogens, and in any case there is fast racemisation in blood abolishing any
putative difference in therapeutic or adverse effects between enantiomers.

Have other people heard of this story? Which is correct, and how did the
incorrect version come into frequent use?


                              Dr. Kurt Giles                     
  Department of Structural Biology   |  e-mail:
  Weizmann Institute of Science      |     vox: +972-8-9343759
  76100 Rehovot, Israel              |     fax: +972-8-9344159
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