Gramine
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| Gramine | |
|---|---|
| Chemical name | 3-(dimethylamino methyl)-indole |
| Chemical formula | C11H14N2 |
| Molecular mass | 174.24 g/mol |
| Melting point | 138-139 °C |
| CAS number | 87-52-5 |
| SMILES | CN(C)CC2=CN C1=CC=CC=C12 |
| NFPA 704 |    |
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| 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.
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[edit] 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.
[edit] Biology
Gramine has been found in the Arundo, silver maple, Hordeum, and Phalaris plant species.
[edit] 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.
[edit] References
- ↑ Corcuera, L. J.; Biochemical basis of the resistance of the barley to aphids. Phytochemistry 1993, 33, 741-747.
- ↑ Orechoff; Norkina; Ber. 1935, 68, 670.
- ↑ Pachter et al. J. Org. Chem. 1959, 24, 1285.
