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Merck
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Documentos Principais

G10806

Sigma-Aldrich

Gramine

97.5%

Sinônimo(s):

3-(Dimethylaminomethyl)indole, Donaxine, NSC 16892

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About This Item

Fórmula empírica (Notação de Hill):
C11H14N2
Número CAS:
Peso molecular:
174.24
Beilstein:
140521
Número CE:
Número MDL:
Código UNSPSC:
12352100
ID de substância PubChem:
NACRES:
NA.22
Ensaio:
97.5%

Nível de qualidade

Ensaio

97.5%

pf

132-134 °C (lit.)

cadeia de caracteres SMILES

CN(C)Cc1c[nH]c2ccccc12

InChI

1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3

chave InChI

OCDGBSUVYYVKQZ-UHFFFAOYSA-N

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Aplicação

Reactant for preparation of:
  • Dopamine D2 receptor antagonists
  • Anti-malarial drugs
  • 5-indolyl-Mannich bases
  • Proliferation inhibitors
  • Inhibitors of human mast cell chymase
  • Preparation of DL-tryptophan
  • Potential detoxification inhibitors of the crucifer phytoalexin brassinin
  • 3-vinylindoles
  • Serotonin 5-HT6 receptor ligand templates
  • Selective protein kinase c delta (PKCδ) down regulators

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Classificações de perigo

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

332.6 °F

Ponto de fulgor (°C)

167 °C


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Timothy Niacaris et al.
The Journal of experimental biology, 206(Pt 2), 223-231 (2002-12-13)
Caenorhabditis elegans feeds by rhythmically contracting its pharynx to ingest bacteria. The rate of pharyngeal contraction is increased by serotonin and suppressed by octopamine. Using an electrophysiological assay, we show that serotonin and octopamine regulate two additional aspects of pharyngeal
Yu Hong et al.
Aquatic toxicology (Amsterdam, Netherlands), 91(3), 262-269 (2009-01-10)
In recent years, the exploration and development of the effective methods of treatment and prevention to algal blooms, especially Microcystis aeruginosa blooms has been an important issue in the field of water environment protection. Allelochemicals (natural plant toxins) are considered
Sebastian Grün et al.
Phytochemistry, 66(11), 1264-1272 (2005-05-24)
Two indole alkaloids with defense related functions are synthesized in the genus Hordeum of the Triticeae. Gramine (3(dimethyl-amino-methyl)-indole) is found in H. spontaneum and in some varieties of H. vulgare, the benzoxazinoid 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA) is detected in H. roshevitzii, H.
Shaoyong Ke et al.
European journal of medicinal chemistry, 54, 248-254 (2012-06-01)
A series of novel gramine analogues were designed and synthesized via a convenient three-component reaction, and which were evaluated for their inhibition activities against cell proliferation. Their structures were confirmed by satisfactory spectra analyses mainly including (1)H NMR, and ESI-MS
Gabriela de la Herran et al.
Organic letters, 9(6), 961-964 (2007-02-20)
Gramine-MeI salts were useful starting materials for the synthesis of 3-benzyl- and 3-allylindoles by the 1,4-addition of boronic acids to the C=C-C=N linkages generated in situ under Rh(I)-catalysis. On the other hand, under Ir(I) catalysis, the reaction of gramines with

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