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G10806

Sigma-Aldrich

Gramine

97.5%

Synonym(s):

3-(Dimethylaminomethyl)indole, Donaxine, NSC 16892

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About This Item

Empirical Formula (Hill Notation):
C11H14N2
CAS Number:
87-52-5
Molecular Weight:
174.24
Beilstein/REAXYS Number:
140521
EC Number:
201-749-8
MDL number:
MFCD00005629
UNSPSC Code:
12352100
PubChem Substance ID:
24895037
NACRES:
NA.22

Quality Level

100

assay

97.5%

mp

132-134 °C (lit.)

SMILES string

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

InChI key

OCDGBSUVYYVKQZ-UHFFFAOYSA-N

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Application

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

332.6 °F

flash_point_c

167 °C

Certificates of Analysis (COA)

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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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