Formula C11H14N2 | Molar mass 174.24 g/mol | |
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Gramine weekend w dolinie jozafata
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.
Contents
Gramine
Occurrence
Gramine has been found in the giant reed, Arundo donax,Acer saccharinum (Silver Maple), Hordeum, (a grass genus that includes barley) and Phalaris(another grass genus).
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 Michael addition to give the very active intermediate 3, which can accept a wide range of nucleophiles to give the desired product 4.
Effects and toxicity
Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).
The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats. Numerous studies have been done on the toxicity in insects harmful to crops for use as a possible insecticide.
Gramine is a norepinephrine reuptake inhibitor in synaptic vesicles.
