Details
| 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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q96A54 Gene ID: 51094.0 Gene Symbol: ADIPOR1 Target Organism: Homo sapiens (Human) |
3.6 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Antimycobacterial indole derivatives]. | 1994 Feb |
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| Novel marine-derived halogen-containing gramine analogues induce vasorelaxation in isolated rat aorta. | 2001 Nov 30 |
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| Activation of MMP-2, cleavage of matrix proteins, and adherens junctions during a snake venom metalloproteinase-induced endothelial cell apoptosis. | 2003 Aug 1 |
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| Serotonin regulates repolarization of the C. elegans pharyngeal muscle. | 2003 Jan |
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| Do naïve ruminants degrade alkaloids in the rumen? | 2005 Apr |
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| Evolution of the indole alkaloid biosynthesis in the genus Hordeum: distribution of gramine and DIBOA and isolation of the benzoxazinoid biosynthesis genes from Hordeum lechleri. | 2005 Jun |
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| Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.). | 2006 Dec 13 |
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| N-Methyltransferase involved in gramine biosynthesis in barley: cloning and characterization. | 2006 Sep |
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| Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts. | 2007 Mar 15 |
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| Synthesis of N-protected staurosporinones. | 2007 Mar 16 |
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| Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters. | 2008 Jan |
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| Classification of rice (Oryza sativa L. Japonica nipponbare) immunophilins (FKBPs, CYPs) and expression patterns under water stress. | 2010 Nov 18 |
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.
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C54677
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C221
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16892
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6890
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m5839
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201-749-8
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C64181
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GRAMINE
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C007884
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136516
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28948
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87-52-5
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
