Q34P - Organic Chemistry (Mcmurry)

Question

Pregabalin, marketed as Lyrica, is an anticonvulsant drug that is also effective in treating chronic pain. The IUPAC name of pregabalin is (S)-3-(aminomethyl)-5-methyl hexanoic acid. (An aminomethyl group is - ${\mathbf{CH}}_{\mathbf{2}}{\mathbf{NH}}_{\mathbf{2}}$.) Draw the structure of pregabalin.

Step-by-Step Solution

Answer

The structure of pregabalin with IUPAC name (S)-3-(aminomethyl)-5-methyl hexanoic acid is

Step1: Definition of structure

The arrangement of chemical bonds between atoms in a molecule is defined as structure.

Step 2: Explanations

As the name pregabalin indicates it is a six-carbon straight-chain carboxylic acid and has an aminomethyl group on $C_3$  and a methyl group on $C_5$.

When viewed from the group of lowest priority, the groups with first, second and third highest priorities are arranged in an anticlockwise direction.

The structure of pregabalin with IUPAC name (S)-3-(aminomethyl)-5-methyl hexanoic acid is