Home Aminos 3-(Dimethylaminomethyl)indole

3-(Dimethylaminomethyl)indole

CAS No.:
87-52-5
Catalog Number:
AG003QTF
Molecular Formula:
C11H14N2
Molecular Weight:
174.2423
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5g
98%(HPLC)
In Stock USA
United States
$43
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25g
98%(HPLC)
In Stock USA
United States
$65
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Product Description
Catalog Number:
AG003QTF
Chemical Name:
3-(Dimethylaminomethyl)indole
CAS Number:
87-52-5
Molecular Formula:
C11H14N2
Molecular Weight:
174.2423
MDL Number:
MFCD00005629
IUPAC Name:
1-(1H-indol-3-yl)-N,N-dimethylmethanamine
InChI:
InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
InChI Key:
OCDGBSUVYYVKQZ-UHFFFAOYSA-N
SMILES:
CN(Cc1c[nH]c2c1cccc2)C
EC Number:
201-749-8
UNII:
FGQ8A78L14
NSC Number:
16892
Properties
Complexity:
168  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
174.116g/mol
Formal Charge:
0
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
174.247g/mol
Monoisotopic Mass:
174.116g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
19A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.8  
Literature
Title Journal
Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. Bioorganic & medicinal chemistry 20121115
Influence of saponins and tannins on intake and nutrient digestion of alkaloid-containing foods. Journal of the science of food and agriculture 20120830
Heterocycle-functional gramine analogues: solvent- and catalyst-free synthesis and their inhibition activities against cell proliferation. European journal of medicinal chemistry 20120801
rac-4-{(E)-[1-Cyano-1-cyclo-hexyl-2-(1H-indol-3-yl)eth-yl]imino-meth-yl}benzonitrile. Acta crystallographica. Section E, Structure reports online 20111201
[(5-Bromo-1H-indol-3-yl)meth-yl]dimethyl-aza-nium nitrate. Acta crystallographica. Section E, Structure reports online 20110701
Found in translation: high-throughput chemical screening in Arabidopsis thaliana identifies small molecules that reduce Fusarium head blight disease in wheat. Molecular plant-microbe interactions : MPMI 20110601
Improved synthesis of 3-(dialkylaminomethyl)-indole in acetic acid aqueous solution under ultrasound irradiation. Ultrasonics sonochemistry 20110101
Differential regulation of 3-aminomethylindole/N-methyl-3-aminomethylindole N-methyltransferase and gramine in barley by both biotic and abiotic stress conditions. Plant physiology and biochemistry : PPB 20110101
A GFP-based assay to quantify the impact of effectors on the ex planta development of the slowly growing barley pathogen Rhynchosporium commune. Mycologia 20110101
The gramine route to pyrido[4,3-b]indol-3-ones - identification of a new cytotoxic lead. Scientia pharmaceutica 20110101
Allele mining in barley genetic resources reveals genes of race-non-specific powdery mildew resistance. Frontiers in plant science 20110101
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
Classification of rice (Oryza sativa L. Japonica nipponbare) immunophilins (FKBPs, CYPs) and expression patterns under water stress. BMC plant biology 20100101
Operons. Cellular and molecular life sciences : CMLS 20091201
Detoxification of gramine by the cereal aphid Sitobion avenae. Journal of chemical ecology 20090301
Gramine-induced growth inhibition, oxidative damage and antioxidant responses in freshwater cyanobacterium Microcystis aeruginosa. Aquatic toxicology (Amsterdam, Netherlands) 20090219
Annotation and expression of carboxylesterases in the silkworm, Bombyx mori. BMC genomics 20090101
Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters. Water research 20080101
A role for gene duplication and natural variation of gene expression in the evolution of metabolism. PloS one 20080101
An antidepressant that extends lifespan in adult Caenorhabditis elegans. Nature 20071122
Naphthoindole-based analogues of tryptophan and tryptamine: synthesis and cytotoxic properties. Bioorganic & medicinal chemistry 20070401
Synthesis of N-protected staurosporinones. The Journal of organic chemistry 20070316
Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts. Organic letters 20070315
Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.). Journal of agricultural and food chemistry 20061213
N-Methyltransferase involved in gramine biosynthesis in barley: cloning and characterization. Phytochemistry 20060901
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
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. Phytochemistry 20050601
Do naïve ruminants degrade alkaloids in the rumen? Journal of chemical ecology 20050401
Gramine: a vasorelaxing alkaloid acting on 5-HT(2A) receptors. Planta medica 20040401
Further characterization of pigment-producing Malassezia strains. Mycoses 20040201
Asymmetric, stereocontrolled total synthesis of paraherquamide A. Journal of the American Chemical Society 20031008
N1-benzenesulfonylgramine and N1-benzenesulfonylskatole: novel 5-HT6 receptor ligand templates. Bioorganic & medicinal chemistry letters 20031006
Activation of MMP-2, cleavage of matrix proteins, and adherens junctions during a snake venom metalloproteinase-induced endothelial cell apoptosis. Experimental cell research 20030801
Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen. The Journal of organic chemistry 20030110
Serotonin regulates repolarization of the C. elegans pharyngeal muscle. The Journal of experimental biology 20030101
Octopaminergic agonists for the cockroach neuronal octopamine receptor. Journal of insect science (Online) 20030101
Diastereoselective reactions in glycine templates containing an ent-ardeemin fragment. The Journal of organic chemistry 20020405
Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence. Organic letters 20020307
Novel marine-derived halogen-containing gramine analogues induce vasorelaxation in isolated rat aorta. European journal of pharmacology 20011130
Gramine increase associated with rapid and transient systemic resistance in barley seedlings induced by mechanical and biological stresses. Plant & cell physiology 20011001
Purification, molecular cloning and mechanism of action of graminelysin I, a snake-venom-derived metalloproteinase that induces apoptosis of human endothelial cells. The Biochemical journal 20010801
Differential inhibition of [3H]-oxotremorine-M and [3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors. Naunyn-Schmiedeberg's archives of pharmacology 20010401
Response of animals to dietary gramine. I. Performance and selected hematological, biochemical and histological parameters in growing chicken, rats and pigs. Archiv fur Tierernahrung 20010101
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. Archiv fur Tierernahrung 20010101
[Antimycobacterial indole derivatives]. Archiv der Pharmazie 19940201
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