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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

Molecular Formula C11H14N2
Molecular Weight 174.2423
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Gramine increase associated with rapid and transient systemic resistance in barley seedlings induced by mechanical and biological stresses.
2001 Oct
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
Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts.
2007 Mar 15
Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters.
2008 Jan
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:17:32 GMT 2023
Edited
by admin
on Sat Dec 16 04:17:32 GMT 2023
Record UNII
FGQ8A78L14
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
NCI_THESAURUS C221
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
Code System Code Type Description
NSC
16892
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
PUBCHEM
6890
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
MERCK INDEX
m5839
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY Merck Index
FDA UNII
FGQ8A78L14
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID3058955
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-749-8
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
NCI_THESAURUS
C64181
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
WIKIPEDIA
GRAMINE
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
MESH
C007884
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
CHEBI
136516
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
CHEBI
28948
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
CAS
87-52-5
Created by admin on Sat Dec 16 04:17:32 GMT 2023 , Edited by admin on Sat Dec 16 04:17:32 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY