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

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

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

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

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.

See also

• Pyrrolidine
• Nipecotic acid
• Vigabatrin