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Gramine information


Gramine
Chemical structure of gramine
Names
Preferred IUPAC name
1-(1H-Indol-3-yl)-N,N-dimethylmethanamine
Other names
donaxine
Identifiers
CAS Number
  • 87-52-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28948 checkY
ChEMBL
  • ChEMBL254348 checkY
ChemSpider
  • 6625 checkY
ECHA InfoCard 100.001.591 Edit this at Wikidata
EC Number
  • 201-749-8
KEGG
  • C08304 checkY
PubChem CID
  • 6890
UNII
  • FGQ8A78L14
CompTox Dashboard (EPA)
  • DTXSID3058955 Edit this at Wikidata
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 checkY
    Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N checkY
  • InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
    Key: OCDGBSUVYYVKQZ-UHFFFAOYAK
SMILES
  • c1cccc2c1c(c[nH]2)CN(C)C
Properties
Chemical formula
C11H14N2
Molar mass 174.24 g/mol
Melting point 138 to 139 °C (280 to 282 °F; 411 to 412 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Gramine (also called donaxine) is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.[1]

  1. ^ Corcuera, L. J. (1993). "Biochemical Basis of the Resistance of the Barley to Aphids". Phytochemistry. 33 (4): 741–747. doi:10.1016/0031-9422(93)85267-U.

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Gramine

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Gramine (also called donaxine) is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants...

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Phalaris arundinacea

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indigenous varieties. Specimens contain varying levels of hordenine and gramine. Leaves of P. arundinacea contain DMT, 5-MeO-DMT and related compounds...

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Desmanthus illinoensis

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NMT, N-hydroxy-N-methyltryptamine, 2-hydroxy-N-methyltryptamine, and gramine (toxic). The plant is nutritious and high in protein. The Land Institute...

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Phalaris aquatica

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countries in South America, and New Zealand. Leaves and seedlings contain gramine. Phalaris aquatica is a pasture species grazed by ruminants. The grass...

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Mannich reaction

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thiophene. Indole is a particularly active substrate; the reaction provides gramine derivatives. The Mannich reaction can be considered to involve a mixed-aldol...

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Phyllodium pulchellum

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and its methyl ether, DMT and its oxides, two tryptamine derivatives, gramine, 15 indole-3-alkylamine, tryptophan bases, β-carbolines Seeds: Galactomannan...

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List of psychoactive plants

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Acer saccharinum (silver maple) was found to contain the indole alkaloid gramine (not active and extremely toxic) 0.05% in the leaves, so it is possible...

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Phalaris brachystachys

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also must be protected from heavy freezes. Some Phalaris species contain gramine, which can cause brain damage, other organ damage, central nervous system...

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Arundo donax

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these compounds than in the United States. Toxins such as bufotenidine and gramine have also been found. The dried rhizome with the stem removed has been...

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Indole alkaloid

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tryptamine. Some simple indole alkaloids do not contain tryptamine, such as gramine and glycozoline (the latter is a derivative of carbazole). Camalexin is...

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Indole

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C3. In this case, C5 is the most common site of electrophilic attack. Gramine, a useful synthetic intermediate, is produced via a Mannich reaction of...

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Boronic acid

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/ tricyclohexylphosphine. Another conjugate addition is that of gramine with phenylboronic acid catalyzed by cyclooctadiene rhodium chloride dimer:...

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Hordenine

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mustard (Sinapis alba) by around 7%; admixture with an equal amount of gramine markedly enhanced this inhibitory effect. Tyramine N-Methyltyramine Candicine...

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C11H14N2

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g/mol, exact mass : 174.115698) may refer to : 6-(2-Aminopropyl)indole Gramine 5-IT α-Methyltryptamine N-Methyltryptamine This set index page lists chemical...

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Acacia obtusifolia

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N-Methyltryptamine, dimethyltryptamine, plus trace betacarbolines, another found gramine. It is highly variable in composition, sometimes devoid of tryptamines...

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Diethyl acetamidomalonate

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rac-tryptophan can be synthesized using diethyl acetamidomalonate and gramine, or through its quaternary ammonium compound which can be obtained with...

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Adiponectin receptor 1

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Ordinary_researchers. Adiponectin ADP-355 ADP-399 AdipoRon (–)-Arctigenin Arctiin Gramine Matairesinol ADP-400 Adiponectin receptor Adiponectin receptor 2 GRCh38:...

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Ryszard Rynkowski

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(later renamed Rampa Theatre). From 1977 to 1978 he was the pianist of the Gramine Blues Group, a Polish vocal/instrumental ensemble. At the same time, he...

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Signaling peptide receptor

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Adiponectin ADP-355 ADP-399 Non-peptide AdipoRon (–)-Arctigenin Arctiin Gramine Matairesinol Antagonists Peptide ADP-400 Agonists Peptide Adiponectin ADP-355...

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Strychnine total synthesis

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skeleton. A Mannich reaction with formaldehyde and dimethylamine) produced gramine 4. Alkylation with iodomethane gave an intermediate quaternary ammonium...

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Theo Holm

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Anthoxanthum odoratum L. (1892) Some new anatomical characters for certain Gramine (1903) Commelinaceœ. Morphological and anatomical studies of the vegetative...

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