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The two enantiomers of a chiral compound can have different activities. For example, one enantiomer of thalidomide has sedative properties, while the other enantiomer is a teratogen.

Question

The two enantiomers of a chiral compound can have different activities. For example, one enantiomer of thalidomide has sedative properties, while the other enantiomer is a teratogen.

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Solution

Yes, it's true. Enantiomers are non-superimposable mirror images of each other, much like left and right hands. This means they have the same molecular formula and the same sequence of bonded atoms, but a different arrangement of atoms in space. This difference can lead to different chemical behavior and different interactions with biological systems.

In the case of thalidomide, one enantiomer (the 'right-handed' version) is effective as a sedative and anti-nausea medication, which was useful for treating morning sickness in pregnant women. However, the other enantiomer (the 'left-handed' version) causes severe birth defects, making it a teratogen.

The tragedy of thalidomide, which was widely prescribed in the late 1950s and early 1960s, was that the drug was administered as a racemic mixture (a 50/50 mix of both enantiomers). At the time, the different effects of the two enantiomers were not understood, and it was not known that one of them was teratogenic.

This case dramatically illustrates the importance of understanding chirality and stereochemistry in drug design and administration.

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