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Gramine



Gramine
IUPAC name 3-(dimethylamino
methyl)-indole
Identifiers
CAS number 87-52-5
SMILES CN(C)CC2=CN
C1=CC=CC=C12
Properties
Molecular formula C11H14N2
Molar mass 174.24 g/mol
Melting point

138-139 °C

Hazards
NFPA 704
1
2
0
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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.[1]

Additional recommended knowledge

Contents

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 retro-Michael addition to give the very active intermediate 3, which can accept a wide range of nucleophiles to give the desired product 4.


Biology

Gramine has been found in the Arundo[2], silver maple[3], Hordeum, and Phalaris plant species.

Synthesis

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.

References

    1. ^  Corcuera, L. J.; Biochemical basis of the resistance of the barley to aphids. Phytochemistry 1993, 33, 741-747.
    2. ^  Orechoff; Norkina; Ber. 1935, 68, 670.
    3. ^  Pachter et al. J. Org. Chem. 1959, 24, 1285.
     
    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.
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