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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Melting Point: | 138.50 °C. @ 760.00 mm Hg
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| Boiling Point: | 293.89 °C. @ 760.00 mm Hg (est)
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| Vapor Pressure: | 0.002000 mmHg @ 25.00 °C. (est) |
| Flash Point: | 269.00 °F. TCC ( 131.50 °C. ) (est)
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| logP (o/w): | 2.177 (est) |
| Soluble in: |
| | water, 3.44e+004 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
intraperitoneal-mouse LD50 122 mg/kg
Psychopharmacologia Vol. 16, Pg. 385, 1970.
intravenous-mouse LD50 46 mg/kg
BEHAVIORAL: EXCITEMENT
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 130, 1952.
intraperitoneal-rat LDLo 250 mg/kg
National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 11, 1953.
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for gramine usage levels up to: | | | not for fragrance use.
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| Recommendation for gramine flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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]- |
Articles:
| 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. |
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3D/inchi