GRAMINE

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 Search

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

Description
Sources: https://doi.org/10.1016/0031-9422(93)85267-U | https://www.ncbi.nlm.nih.gov/pubmed/23691032 | https://doi.org/10.1016/S0031-9422(00)80376-3

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
Adiponectin receptor protein 1 6 Target ID: Q96A54 Gene ID: 51094.0 Gene Symbol: ADIPOR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23691032	Agonist 2752		3.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23691032	Preventing		Basic research	Unknown Approved Use Unknown
Oral cancer 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28887922	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Classification of rice (Oryza sativa L. Japonica nipponbare) immunophilins (FKBPs, CYPs) and expression patterns under water stress.	2010-11-18	21087465
Operons.	2009-12	19662496
Annotation and expression of carboxylesterases in the silkworm, Bombyx mori.	2009-11-24	19930670
Detoxification of gramine by the cereal aphid Sitobion avenae.	2009-03	19224277
Gramine-induced growth inhibition, oxidative damage and antioxidant responses in freshwater cyanobacterium Microcystis aeruginosa.	2009-02-19	19131120
A role for gene duplication and natural variation of gene expression in the evolution of metabolism.	2008-03-19	18350173
Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters.	2008-01	17692886
Naphthoindole-based analogues of tryptophan and tryptamine: synthesis and cytotoxic properties.	2007-04-01	17276690
Synthesis of N-protected staurosporinones.	2007-03-16	17309305
Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts.	2007-03-15	17305348
Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.).	2006-12-13	17147408
N-Methyltransferase involved in gramine biosynthesis in barley: cloning and characterization.	2006-09	16930646
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.	2005-06	15907959
Do naïve ruminants degrade alkaloids in the rumen?	2005-04	16124250
Gramine: a vasorelaxing alkaloid acting on 5-HT(2A) receptors.	2004-04	15095157
Further characterization of pigment-producing Malassezia strains.	2004-02	14998397
Asymmetric, stereocontrolled total synthesis of paraherquamide A.	2003-10-08	14519003
N1-benzenesulfonylgramine and N1-benzenesulfonylskatole: novel 5-HT6 receptor ligand templates.	2003-10-06	12951125
Activation of MMP-2, cleavage of matrix proteins, and adherens junctions during a snake venom metalloproteinase-induced endothelial cell apoptosis.	2003-08-01	12878166
Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen.	2003-01-10	12515475
Serotonin regulates repolarization of the C. elegans pharyngeal muscle.	2003-01	12477893
Octopaminergic agonists for the cockroach neuronal octopamine receptor.	2003	15841226
Diastereoselective reactions in glycine templates containing an ent-ardeemin fragment.	2002-04-05	11925204
Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.	2002-03-07	11869135
Novel marine-derived halogen-containing gramine analogues induce vasorelaxation in isolated rat aorta.	2001-11-30	11734189
Gramine increase associated with rapid and transient systemic resistance in barley seedlings induced by mechanical and biological stresses.	2001-10	11673626
Purification, molecular cloning and mechanism of action of graminelysin I, a snake-venom-derived metalloproteinase that induces apoptosis of human endothelial cells.	2001-08-01	11463342
Differential inhibition of [3H]-oxotremorine-M and [3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors.	2001-04	11330337
Response of animals to dietary gramine. II. Effects of feeding high-gramine yellow lupin seeds on reproductive performance of rats and on selected hematological and biochemical parameters in offspring.	2001	11901977
Response of animals to dietary gramine. I. Performance and selected hematological, biochemical and histological parameters in growing chicken, rats and pigs.	2001	11901976
[Antimycobacterial indole derivatives].	1994-02	8135641

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 21:21:23 GMT 2025` Edited by `admin` on `Mon Mar 31 21:21:23 GMT 2025`
Record UNII	FGQ8A78L14
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-16892

Preferred Name

English

GRAMINE

Common Name

English

DONAXINE

Common Name

English

.BETA.-(DIMETHYLAMINOMETHYL)INDOLE

Common Name

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