| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H14N2 |
| Molecular Weight | 174.2423 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CC1=CNC2=C1C=CC=C2
InChI
InChIKey=OCDGBSUVYYVKQZ-UHFFFAOYSA-N
InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
Gramine (aka donaxine) is a naturally occurring indole alkaloid that can be found in several plant species. It is toxic to many organisms and may be a natural defense mechanism for these plants. Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1) which plays an important role in the suppression of metabolic disorders that can result in type 2 diabetes, obesity, and atherosclerosis.
Originator
Approval Year
PubMed
Sample Use Guides
Three doses (50 mg/kg, 100 mg/kg, and 150 mg/kg) were administered orally to Swiss albino mice for 48 h to study the genotoxic activity in micronucleus assay as well as any chromosomal aberration. Gramine at the given dose lacks mutagenicity as well as found to possess antimutagenic efficacy.
Route of Administration:
Oral
Human MCF-7 and MDA-MB-231 cells were maintained in DMEM containing 10% fetal bovine serum and supplied with 1% penicillin/streptomycin. Cells were incubated at37 deg-C in a 5% CO2 atmosphere. Cells were grown to 80% confluence and aliquoted into 100 mm dishes in serum-free media. Cells were allowed to attach overnight and 5 micro-L culture media containing gramine was added. Cells were incubated with 20 µM to 1.2 nM gramine for 72 hours after which proliferation was evaluated using CellTilter-Blue reagent. Gramine inhibited the growth of MDA-MB-231 and MCF-7 cells with IC50 values of 15.3 and 10.6 micro-M respectively.
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
