Isonipecotic acid

Isonipecotic acid is an organic compound with the formula C6H11NO2. It is a carboxylic acid that contains a pyrrolidine ring, and is a structural isomer of nipecotic acid. Isonipecotic acid is used in the synthesis of various pharmaceuticals, including some antiepileptic drugs.

Structure and properties[edit | edit source]

Isonipecotic acid consists of a five-membered pyrrolidine ring, which contains a nitrogen atom, and a carboxylic acid group. The presence of the nitrogen atom makes the compound a heterocycle. The carboxylic acid group can participate in hydrogen bonding, which can affect the compound's physical properties and reactivity.

Synthesis[edit | edit source]

Isonipecotic acid can be synthesized from glutaric acid or its derivatives, in a process that involves the formation of a cyclic compound and subsequent functional group transformations.

Applications[edit | edit source]

Isonipecotic acid is used as a building block in the synthesis of various pharmaceuticals. For example, it is used in the synthesis of vigabatrin, an antiepileptic drug. The compound's pyrrolidine ring can act as a bioisostere for the GABA neurotransmitter, which can enhance the activity of GABA in the brain and help to control seizures.

Safety[edit | edit source]

As with all chemicals, isonipecotic acid should be handled with care. It can cause skin and eye irritation, and may be harmful if swallowed or inhaled.