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Gramine (Molecule of the Month for October 2011)


Gramine 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. Gramine has been found in the giant reed, Arundo donax, Acer saccharinum (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.

Gramine is used mostly in synthetic organic chemistry as a starting material for tryptophan syntheses.

Formal Chemical Name (IUPAC)



Picture of Gramine

click on the picture above to interact
with the 3D model of the
Gramine structure
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Picture of Gramine


Update by Karl Harrison
(Molecule of the Month for October 2011 )