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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 3D model

click on the picture of  Gramine above to interact
with the 3D model of the
Gramine structure
(this will open a new browser window)

Picture of Gramine


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

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