Gramine

Gramine

Names
IUPAC name 1-(1H-indol-3-yl)-N,N-dimethylmethanamine
Identifiers
CAS Number	87-52-5 Y
ChEMBL	ChEMBL254348 Y
ChemSpider	6625 Y
Jmol 3D model	Interactive image
KEGG	C08304 Y
InChI InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 Y Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N Y InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 Key: OCDGBSUVYYVKQZ-UHFFFAOYAK
SMILES c1cccc2c1c(cn2)CN(C)C
Properties
Chemical formula	C11H14N2
Molar mass	174.24 g/mol
Melting point	138 to 139 °C (280 to 282 °F; 411 to 412 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox 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.

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).

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.

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.