<p>Due to its long history, thalidomide, introduced as a tranquilizer in 1957, and thereafter prescribed for a variety of physiological ailments, has been studied for a very long time; this includes the determination of its crystal structure many times since 1971 as both the enantiomeric species and the racemic mixture. It has a long and notorious medical and legal record. Thus, it seemed that the substance was thoroughly scientifically studied and needed no additional documentation until now. However, recently, we discovered that this crystalline material belongs in the newly described class of Racemic Mimics. Below, we describe the crystal structure of two of its polymorphs which demonstrate that it neatly falls in that category and that it exists in racemic and chiral forms in which the cell constants are almost identical, while fulfilling the fundamental condition that Z’ (chiral) / Z’ (racemic) = 2.0. And, thanks to one of our reviewers for pointing us to the work, the material here presented has been published by another group of researchers (discussed below).</p>

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Racemic mimic crystal pairs-part 8. thalidomide – a feared blessing/curse of yore - a crystallographic analysis

  • Ivan Bernal,
  • Roger A. Lalancette

摘要

Due to its long history, thalidomide, introduced as a tranquilizer in 1957, and thereafter prescribed for a variety of physiological ailments, has been studied for a very long time; this includes the determination of its crystal structure many times since 1971 as both the enantiomeric species and the racemic mixture. It has a long and notorious medical and legal record. Thus, it seemed that the substance was thoroughly scientifically studied and needed no additional documentation until now. However, recently, we discovered that this crystalline material belongs in the newly described class of Racemic Mimics. Below, we describe the crystal structure of two of its polymorphs which demonstrate that it neatly falls in that category and that it exists in racemic and chiral forms in which the cell constants are almost identical, while fulfilling the fundamental condition that Z’ (chiral) / Z’ (racemic) = 2.0. And, thanks to one of our reviewers for pointing us to the work, the material here presented has been published by another group of researchers (discussed below).