Gramine

From Wikipedia, the free encyclopedia

Gramine
Chemical structure of 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]

Contents

[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.

Retromichael addition of gramine

[edit] Biology

Gramine has been found in the Arundo,[2] silver maple,[3] 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.

Gramine can be synthesized from indole

[edit] References

 The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.
  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.
Languages