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G10806

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24895037
EC Number:
201-749-8
Beilstein/REAXYS Number:
140521
MDL number:
MFCD00005629
Assay:
97.5%
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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

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

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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

flash_point_f

332.6 °F

flash_point_c

167 °C

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Certificates of Analysis (COA)

Lot/Batch Number
00514CV

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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.
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