Gramine (Molecule of the Month for October 2011)
Donaxine
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)
1-(1H-indol-3-yl)-N,N-dimethylmethanamine
References
click on the picture of Gramine above to interact
with the 3D model of the
Gramine structure
(this will open a new browser window)
C11H14N2
Update by Karl Harrison
(Molecule of the Month for
October 2011
)
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