Grief

Structural formula
General
Surname	Grief
Molecular formula	C 11 H 14 N 2
External identifiers / databases
CAS number 87-52-5 EC number 201-749-8 ECHA InfoCard 100.001.591 PubChem 6890 Wikidata Q420118
properties
Molar mass	174.25 g mol −1
Physical state	firmly
Melting point	138-139 ° C
solubility	practically insoluble in water
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	122 mg kg −1 ( LD 50 ,  mouse ,  ip ) 46 mg kg −1 ( LD 50 ,  mouse ,  iv ) 250 mg kg −1 ( LD 50 ,  rat ,  ip )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Gramin (also Donaxin is called) a naturally occurring in various plant species indole - alkaloids . Gramin could play a role in the self defense of plants because it is toxic to various organisms.

Occurrence and characteristics

Gramin has been found in cereals , cauliflower , silver poplar and glossy grass . On grazing livestock such as B. Sheep , gramin is deleterious, while it is low in toxicity to mice and rats.

use

Gramin is mostly used in organic chemistry as a starting material for tryptophan synthesis.

All of Gramin's reactions follow the same general reaction scheme:

1. Gramin is treated with a strongly electrophilic substance such as B. methyl iodide added to form a quaternary ammonium salt
2. The ammonium salt undergoes Hofmann elimination or Michael addition to give the very active intermediate 3
3. which can combine with a wide variety of nucleophilic particles to give the desired product 4

synthesis

Although found in many different plants, gramin is much easier to synthesize directly from indole via the Mannich reaction with dimethylamine and formaldehyde .

Individual evidence

1. ↑ ^{a b c} Entry for CAS no. 87-52-5 in the GESTIS substance database of the IFA , accessed on July 14, 2011 (JavaScript required)
2. ↑ ^{a b c d} Entry on Gramin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
3. ↑ GL Marten, RM Jordan, AW Hovin: Biological significance of reed canarygrass alkaloids and association with palatability variation to grazing in sheep and cattle , Agronomy Journal 68 (1976), pp. 909-914.

literature

• LJ Corcuera: "Biochemical basis of the resistance of the barley to aphids", Phytochemistry 1993 , 33 , 741-747.
• Orechoff; Norkina: Chemical reports 1935 , 68 , 670.
• Pachter et al .: J. Org. Chem. 1959 , 24 , 1285.