To use all functions of this page, please activate cookies in your browser.
With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter.
- My watch list
- My saved searches
- My saved topics
- My newsletter
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.
Additional recommended knowledge
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 nucleophiles to give the desired product 4.
Gramine has been found in the Arundo, silver maple, Hordeum, and Phalaris plant species.
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.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Gramine". A list of authors is available in Wikipedia.|