Nepeta cataria, or the catnip plant, is known for its stimulant effect on cats. The active compound in the plant – (cis,trans)-nepetalactone (Figure 1) – has a five-membered ring that is fused to a six-membered ring. This ring contains a cyclic ester, or lactone, and a C=C double bond. It also has three chiral carbons (indicated by the wedges).
The cis in (cis,trans)-nepetalactone refers to the stereochemistry of the ring junction, where both hydrogens are pointing in the same direction. The prefix trans indicates that the methyl substituent is on the opposite side of the molecule from the lactone group. Only the (cis,trans)-isomer affects cats. This a further example of how different stereoisomers can have different biological effects. This was infamously illustrated by thalidomide, which was prescribed for morning sickness during pregnancy but caused deformities in the fetus – an effect caused by only one of the optical isomers of the drug.
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