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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
Structure of GRAMINE

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

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q96A54
Gene ID: 51094.0
Gene Symbol: ADIPOR1
Target Organism: Homo sapiens (Human)
3.6 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Antimycobacterial indole derivatives].
1994 Feb
Differential inhibition of [3H]-oxotremorine-M and [3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors.
2001 Apr
Gramine increase associated with rapid and transient systemic resistance in barley seedlings induced by mechanical and biological stresses.
2001 Oct
Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.
2002 Mar 7
Octopaminergic agonists for the cockroach neuronal octopamine receptor.
2003
Activation of MMP-2, cleavage of matrix proteins, and adherens junctions during a snake venom metalloproteinase-induced endothelial cell apoptosis.
2003 Aug 1
Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen.
2003 Jan 10
Asymmetric, stereocontrolled total synthesis of paraherquamide A.
2003 Oct 8
Further characterization of pigment-producing Malassezia strains.
2004 Feb
Naphthoindole-based analogues of tryptophan and tryptamine: synthesis and cytotoxic properties.
2007 Apr 1
Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters.
2008 Jan
A role for gene duplication and natural variation of gene expression in the evolution of metabolism.
2008 Mar 19
Detoxification of gramine by the cereal aphid Sitobion avenae.
2009 Mar
Annotation and expression of carboxylesterases in the silkworm, Bombyx mori.
2009 Nov 24
Classification of rice (Oryza sativa L. Japonica nipponbare) immunophilins (FKBPs, CYPs) and expression patterns under water stress.
2010 Nov 18
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: the referenced study was conducted on mice
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.
Name Type Language
GRAMINE
MI  
Common Name English
DONAXINE
Common Name English
.BETA.-(DIMETHYLAMINOMETHYL)INDOLE
Common Name English
NSC-16892
Code English
GRAMINE [MI]
Common Name English
3-((DIMETHYLAMINO)METHYL)INDOLE
Systematic Name English
3-(N,N-DIMETHYLAMINOMETHYL)INDOLE
Systematic Name English
3-(DIMETHYLAMINOMETHYL)INDOLE
Systematic Name English
N,N-DIMETHYL-1H-INDOLE-3-METHANAMINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C54677
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
NCI_THESAURUS C221
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
Code System Code Type Description
NSC
16892
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
PUBCHEM
6890
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
MERCK INDEX
m5839
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY Merck Index
FDA UNII
FGQ8A78L14
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
EPA CompTox
DTXSID3058955
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-749-8
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
NCI_THESAURUS
C64181
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
WIKIPEDIA
GRAMINE
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
MESH
C007884
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
CHEBI
136516
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
CHEBI
28948
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY
CAS
87-52-5
Created by admin on Sat Dec 16 04:17:32 UTC 2023 , Edited by admin on Sat Dec 16 04:17:32 UTC 2023
PRIMARY