G10806

Sigma-Aldrich

Gramine

99%

Synonym(s):
Donaxine, 3-(Dimethylaminomethyl)indole, NSC 16892
Empirical Formula (Hill Notation):
C11H14N2
CAS Number:
Molecular Weight:
174.24
Beilstein/REAXYS Number:
140521
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

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

Packaging

25 g in poly bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

332.6 °F

Flash Point(C)

167 °C

Certificate of Analysis

Certificate of Origin

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....
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...
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...
Miho Chikazawa et al.
Journal of nutritional science and vitaminology, 64(1), 68-74 (2018-03-02)
Maintaining skeletal muscle functions by controlling muscle metabolism is of utmost importance. β2-Adrenergic receptor (β2-AR), which is expressed in skeletal muscle, is a member of the G-protein-coupled receptor family that plays a critical role in the maintenance of muscle mass....
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...

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