[pi-roh-li-deen, -din, -rol-i-]

Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula C4H9N. It is a cyclic amine with a five-membered ring containing four carbon atoms and one nitrogen atom. It is a clear liquid with an unpleasant ammonia-like odor.

Pyrrolidine is found naturally in the leaves of tobacco and carrot. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine. It is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam).

A pyrrolidine ring is the central structure of the amino acids proline and hydroxyproline.

In organic chemistry, pyrrolidine is used to activate ketones toward nucleophilic addition by formation of the imine.

See also

  • Pyrrole, the aromatic analog with two double bonds
  • Pyrroline, an analog with one double bond

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