1H-indole-3-methanamine, N,N-dimethyl-

CAS: 87-52-5 C11 H14 N2 MW: 174.24658000

Identification

Namegramine
IUPAC1-(1H-indol-3-yl)-N,N-dimethylmethanamine
CAS Number87-52-5
EINECS201-749-8
FDA UNIIFGQ8A78L14
Molecular FormulaC11 H14 N2
Molecular Weight174.24658000
MDL NumberMFCD00005629
Nikkaji NumberJ10.618F
Beilstein140521
XlogP31.80 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 138.50 °C. @ 760.00 mm Hg
Boiling Point 293.89 °C. @ 760.00 mm Hg (est)
Vapor Pressure 0.002000 mmHg @ 25.00 °C. (est)
Flash Point 269.00 °F. TCC ( 131.50 °C. ) (est)
logP (o/w) 2.177 (est)
Soluble in water, 3.44e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 122 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for gramine usage levels up tonot for fragrance use.
Recommendation for gramine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

barley leaf barley protoplast barley root barley shoot barley shoot barley sprout cabbage lupinus spp. wheat leaf

Synonyms

N,N- dimethyl-1H-indole-3-methanamine 3-(( dimethylamino)methyl)indole 3-[( dimethylamino)methyl]indole 3-( dimethylaminomethyl)indole donaxin donaxine (1H- indol-3-yl)-N,N-dimethylmethanamine 1-(1H- indol-3-yl)-N,N-dimethylmethanamine (1H- indol-3-ylmethyl)-dimethyl-amine N-(1H- indol-3-ylmethyl)-N,N-dimethylamine indol-3-ylmethyl)dimethylamine (1H- indol-3-ylmethyl)dimethylamine 1H- indole-3-methanamine, N,N-dimethyl- indole, 3-[(dimethylamino)methyl]- PubMed: Xenobiotic metabolism of plant secondary compounds in the English grain aphid, Sitobion avenae (F.) (Hemiptera: Aphididae). PubMed: Discovery of gramine derivatives that inhibit the early stage of EV71 replication in vitro. PubMed: Natural xenobiotics to prevent cyanobacterial and algal growth in freshwater: contrasting efficacy of tannic acid, gallic acid, and gramine. PubMed: Scandium triflate-catalyzed nucleophilic additions to indolylmethyl Meldrum's acid derivatives via a gramine-type fragmentation: synthesis of substituted indolemethanes. PubMed: An ABC pleiotropic drug resistance transporter of Fusarium graminearum with a role in crown and root diseases of wheat. PubMed: Glutathione S-transferase of brown planthoppers (Nilaparvata lugens) is essential for their adaptation to gramine-containing host plants. PubMed: Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay. PubMed: [Synthesis of indole compounds using multifunctional synthons]. PubMed: Avena sativa (Oat), a potential neutraceutical and therapeutic agent: an overview. PubMed: Heterocycle-functional gramine analogues: solvent- and catalyst-free synthesis and their inhibition activities against cell proliferation. PubMed: Influence of saponins and tannins on intake and nutrient digestion of alkaloid-containing foods. PubMed: rac-4-{(E)-[1-Cyano-1-cyclo-hexyl-2-(1H-indol-3-yl)eth-yl]imino-meth-yl}benzonitrile. PubMed: [(5-Bromo-1H-indol-3-yl)meth-yl]dimethyl-aza-nium nitrate. PubMed: The gramine route to pyrido[4,3-b]indol-3-ones - identification of a new cytotoxic lead. PubMed: A GFP-based assay to quantify the impact of effectors on the ex planta development of the slowly growing barley pathogen Rhynchosporium commune. PubMed: Found in translation: high-throughput chemical screening in Arabidopsis thaliana identifies small molecules that reduce Fusarium head blight disease in wheat. PubMed: Differential regulation of 3-aminomethylindole/N-methyl-3-aminomethylindole N-methyltransferase and gramine in barley by both biotic and abiotic stress conditions. PubMed: Improved synthesis of 3-(dialkylaminomethyl)-indole in acetic acid aqueous solution under ultrasound irradiation. PubMed: Detoxification of gramine by the cereal aphid Sitobion avenae. PubMed: Gramine-induced growth inhibition, oxidative damage and antioxidant responses in freshwater cyanobacterium Microcystis aeruginosa. PubMed: Coupling of activated esters to gramines in the presence of ethyl propiolate under mild conditions. PubMed: Synthesis of N-protected staurosporinones. PubMed: Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts. PubMed: Naphthoindole-based analogues of tryptophan and tryptamine: synthesis and cytotoxic properties. PubMed: Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.). PubMed: N-Methyltransferase involved in gramine biosynthesis in barley: cloning and characterization. PubMed: Do naïve ruminants degrade alkaloids in the rumen? PubMed: 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. PubMed: Gramine: a vasorelaxing alkaloid acting on 5-HT(2A) receptors. PubMed: Further characterization of pigment-producing Malassezia strains. PubMed: Asymmetric, stereocontrolled total synthesis of paraherquamide A. PubMed: N1-benzenesulfonylgramine and N1-benzenesulfonylskatole: novel 5-HT6 receptor ligand templates. PubMed: Titres of biogenic amines and ecdysteroids: effect of octopamine on the production of ecdysteroids in the silkworm Bombyx mori. PubMed: Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen. PubMed: Serotonin regulates repolarization of the C. elegans pharyngeal muscle. PubMed: Diastereoselective reactions in glycine templates containing an ent-ardeemin fragment. PubMed: 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. PubMed: Response of animals to dietary gramine. I. Performance and selected hematological, biochemical and histological parameters in growing chicken, rats and pigs. PubMed: Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence. PubMed: Novel marine-derived halogen-containing gramine analogues induce vasorelaxation in isolated rat aorta. PubMed: Gramine increase associated with rapid and transient systemic resistance in barley seedlings induced by mechanical and biological stresses. PubMed: Differential inhibition of [3H]-oxotremorine-M and [3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors. PubMed: Alkaloid-fullerene systems through photocycloaddition reactions. PubMed: Effect of octopamine on the activity of juvenile-hormone esterase in the silkworm Bombyx mori and the red flour beetle Tribolium freemani. PubMed: Structure-activity relationship of gramine derivatives in Ca(2+) release from sarcoplasmic reticulum. PubMed: Transmembrane domain I contributes to the permeation pathway for serotonin and ions in the serotonin transporter. PubMed: Xylocain (lidocaine, lignocaine), its discovery and Gordh's contribution to its clinical use. PubMed: A simple and sensitive quantitation of N,N-dimethyltryptamine by gas chromatography with surface ionization detection. PubMed: Indole alkaloids from Antirhea lucida. PubMed: Intrinsic neuromodulation in the Tritonia swim CPG: serotonin mediates both neuromodulation and neurotransmission by the dorsal swim interneurons. PubMed: NMR-titrations with complexes between ds-DNA and indole derivatives including tryptophane containing peptides. PubMed: Solid-surface room-temperature phosphorescence detection of serotonin, tryptamine, and gramine enhanced by inorganic salts and sodium dodecyl sulfate. PubMed: Gramine and free amino acids as indicators of fluoride-induced stress in barley and its consequences to insect herbivory. PubMed: Multiple receptors mediate the modulatory effects of serotonergic neurons in a small neural network. PubMed: Possible NMDA antagonist properties of drugs that affect high pressure neurological syndrome. PubMed: Characterization of tyramine and octopamine receptors in the insect (Locusta migratoria migratorioides) brain. PubMed: Effect of hormones and hormone-induced imprinting on the serotonin level in Tetrahymena: immunocytochemical studies. PubMed: Biologically active secondary metabolites of barley. III. A method for identification and quantification of hordenine and gramine in barley by high-performance liquid chromatography. PubMed: Biologically active secondary metabolites of barley. II. Phytotoxicity of barley allelochemicals. PubMed: Effects of the Alkaloid Gramine on the Light-Harvesting, Energy Transfer, and Growth of Anabaena sp. (PCC 7119). PubMed: Relationship between deterrence and toxicity of plant secondary compounds for the grasshopperSchistocerca americana. PubMed: Regulation by 1,4-diamines of the ornithine decarboxylase activity induced by ornithine in perifused tumor cells. PubMed: Characterization and pharmacological studies of an octopamine-sensitive adenylate cyclase from nerve cord of Locusta migratoria. PubMed: Honeydew analysis for detecting phloem transport of plant natural products : Implications for host-plant resistance to sap-sucking insects. PubMed: Effects of starvation and neuroactive drugs on feeding in Caenorhabditis elegans. PubMed: Ovine white-liver disease (OWLD). Botanical and chemical composition of pasture grass. PubMed: Role of dopamine and indolamine derivatives in the regulation of the sea urchin adenylate cyclase. PubMed: Experimental evidence that tryptamine alkaloids do not cause Phalaris aquatica sudden death syndrome in sheep. PubMed: Identification of minor nitrosation products of the alkaloid gramine by mass spectrometry. PubMed: Evidence for serotonin synthesis, uptake, and release in dissociated rat sympathetic neurons in culture. PubMed: Synthesis of N1-nitroso-3-nitromethylindole: a nonvolatile N-nitroso compound isolated from the nitrosation of the alkaloid gramine. PubMed: Induction of a Specific N-Methyltransferase Enzyme by Long-Term Heat Stress during Barley Leaf Growth. PubMed: Isolation and characterization of products from the nitrosation of the alkaloid gramine. PubMed: Molecular mechanism of action of 5,6-dihydroxytryptamine. Synthesis and biological evaluation of 4-methyl-, 7-methyl-, and 4,7-dimethyl-5,6-dihydroxytryptamines. PubMed: Effects of gramine on energy metabolism of rat and bovine mitochondria. PubMed: Rapid formation of N-nitrosodimethylamine from gramine, a naturally occurring precursor in barley malt. PubMed: Pharmacology of aminergic receptors mediating an elevation in cyclic AMP and release of hormone from locust neurosecretory cells. PubMed: On the role of serotonin and 5-methoxy-tryptamine in the regulation of cell division in sea urchin eggs. PubMed: Gramine Accumulation in Leaves of Barley Grown under High-Temperature Stress. PubMed: Attempt to disturb receptor memory in a unicellular (Tetrahymena) model system. PubMed: Regulation of adenylate cyclase and cyclic AMP phosphodiesterase by 5-hydroxytryptamine and calcium ions in blowfly salivary-gland homogenates. PubMed: N-nitrosodimethylamine in malt beverages--anticipatory action by the brewing industry. PubMed: Effect of combined and repeated hormone treatment on the growth of the Tetrahymena. PubMed: N-nitrosodimethylamine precursors in malt. PubMed: Degradation of Gramine by Cell Suspension Cultures of Barley (Hordeum vulgare). PubMed: Acyl lipids, pigments, and gramine in developing leaves of barley and its virescens mutant. PubMed: Some hematological and histopathological effects of the alkaloids gramine and hordenine on meadow voles (Microtus pennsylvanicus). PubMed: Effect of hormones and related compounds on the multiplication of Tetrahymena. PubMed: Serotonin and dopamine as neurotransmitters in mytilus: block of serotonin receptors by an organic mercurial. PubMed: Aphylline, epiaphylline, 10,17-dioxosparteine, gramine, and other unexpected alkaloids from Lupinus hartwegii. PubMed: The action of 5-hydroxytryptamine on chemoreceptor discharges of the cat's carotid body. PubMed: The nature of the binding between LSD and a 5-HT receptor: a possible explanation for hallucinogenic activity. PubMed: The biogenesis of gramine. PubMed: Metabolic fates of gramine in barley. II. Biotransformation of gramine into indole-3-carbinol and indole-3-carboxylic acid in barley. PubMed: Metabolic fates of gramine in barley. I. Mechanism of incorporation of gramine into tryptophan in barley shoots. PubMed: A metabolic pathway of gramine in barley. PubMed: The subcellular fractions in the biosynthesis of natural compounds. I. Gramine alkaloids. PubMed: The biotransformation of gramine into tryptophan in barley shoots. PubMed: BENZO(B)THIOPHENE DERIVATIVES. IV. THE PREPARATION AND PHARMACOLOGICAL ACTIVITY OF COMPOUNDS RELATED TO SEROTONIN AND GRAMINE. PubMed: A note on the occurrence of gramine in Acer rubrum L. PubMed: The ontogenesis of gramine in barley seedlings. PubMed: Gramine derivatives antagonistic to 5-hydroxytryptamine (enteramine). PubMed: [Synthesis of gramine substituted to give substances with anti-5-hydroxytryptamine activity]. PubMed: The alkylation of aliphatic nitro compounds with gramine; a new synthesis of derivatives of tryptamine. PubMed: The chemistry of nitroacetic acid and its esters; the alkylation of alkylnitroacetates with gramine.