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 2678		3.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 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
[Antimycobacterial indole derivatives].	1994 Feb	8135641
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
Differential inhibition of [3H]-oxotremorine-M and [3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors.	2001 Apr	11330337
Purification, molecular cloning and mechanism of action of graminelysin I, a snake-venom-derived metalloproteinase that induces apoptosis of human endothelial cells.	2001 Aug 1	11463342
Novel marine-derived halogen-containing gramine analogues induce vasorelaxation in isolated rat aorta.	2001 Nov 30	11734189
Gramine increase associated with rapid and transient systemic resistance in barley seedlings induced by mechanical and biological stresses.	2001 Oct	11673626
Diastereoselective reactions in glycine templates containing an ent-ardeemin fragment.	2002 Apr 5	11925204
Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.	2002 Mar 7	11869135
Octopaminergic agonists for the cockroach neuronal octopamine receptor.	2003	15841226
Activation of MMP-2, cleavage of matrix proteins, and adherens junctions during a snake venom metalloproteinase-induced endothelial cell apoptosis.	2003 Aug 1	12878166
Serotonin regulates repolarization of the C. elegans pharyngeal muscle.	2003 Jan	12477893
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	12515475
N1-benzenesulfonylgramine and N1-benzenesulfonylskatole: novel 5-HT6 receptor ligand templates.	2003 Oct 6	12951125
Asymmetric, stereocontrolled total synthesis of paraherquamide A.	2003 Oct 8	14519003
Gramine: a vasorelaxing alkaloid acting on 5-HT(2A) receptors.	2004 Apr	15095157
Further characterization of pigment-producing Malassezia strains.	2004 Feb	14998397
Do naïve ruminants degrade alkaloids in the rumen?	2005 Apr	16124250
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	15907959
Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.).	2006 Dec 13	17147408
N-Methyltransferase involved in gramine biosynthesis in barley: cloning and characterization.	2006 Sep	16930646
Naphthoindole-based analogues of tryptophan and tryptamine: synthesis and cytotoxic properties.	2007 Apr 1	17276690
Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts.	2007 Mar 15	17305348
Synthesis of N-protected staurosporinones.	2007 Mar 16	17309305
Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters.	2008 Jan	17692886
A role for gene duplication and natural variation of gene expression in the evolution of metabolism.	2008 Mar 19	18350173
Operons.	2009 Dec	19662496
Gramine-induced growth inhibition, oxidative damage and antioxidant responses in freshwater cyanobacterium Microcystis aeruginosa.	2009 Feb 19	19131120
Detoxification of gramine by the cereal aphid Sitobion avenae.	2009 Mar	19224277
Annotation and expression of carboxylesterases in the silkworm, Bombyx mori.	2009 Nov 24	19930670
Classification of rice (Oryza sativa L. Japonica nipponbare) immunophilins (FKBPs, CYPs) and expression patterns under water stress.	2010 Nov 18	21087465

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 `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

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Name

Type

Language

GRAMINE

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