Information About

Gramine









Gramine (also called donaxine) is a naturally occurring Indole Alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.


USES

Gramine is used mostly in Synthetic Organic Chemistry as a starting material for Tryptophan syntheses.

All reactions of gramine follow the same general reaction scheme. Gramine is reacted with a strong Electrophile , such as Methyl Iodide , to form the quaternary ammonium salt 2. The ammonium salt will undergo a Hofmann Elimination or Retro-Michael Addition to give the very active intermediate '''3''', which can accept a wide range of Nucleophile s to give the desired product '''4'''.


BIOLOGY

Gramine has been found in the Arundo , Silver Maple , Hordeum , and Phalaris plant species.


SYNTHESIS

Despite being widely available in several plant species, gramine is far easier to synthesize directly from indole via a Mannich Reaction with Dimethylamine and Formaldehyde .


REFERENCES