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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:
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

Signal Word

Warning

Hazard Statements

H302 + H312

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

332.6 °F

Flash Point(C)

167 °C

Certificates of Analysis (COA)

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Robert M Williams et al.
Journal of the American Chemical Society, 125(40), 12172-12178 (2003-10-02)
The first total synthesis of paraherquamide A, a potent anthelmintic agent isolated from various Penicillium sp. with promising activity against drug-resistant intestinal parasites, is reported. Key steps in this asymmetric, stereocontrolled total synthesis include a new enantioselective synthesis of alpha-alkylated-beta-hydroxyproline
E L Barker et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 19(12), 4705-4717 (1999-06-15)
Mutation of a conserved Asp (D98) in the rat serotonin (5HT) transporter (rSERT) to Glu (D98E) led to decreased 5HT transport capacity, diminished coupling to extracellular Na+ and Cl-, and a selective loss of antagonist potencies (cocaine, imipramine, and citalopram
Brian Chauder et al.
Organic letters, 4(5), 815-817 (2002-03-01)
[reaction: see text] In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields. A conceptually new
Jacob Owens et al.
Journal of the science of food and agriculture, 92(11), 2373-2378 (2012-03-21)
We hypothesized that eating a food containing saponins (SAP), or tannins (TAN) prior to foods containing the alkaloids gramine (GRA) or 5-methoxy-N,N-dimethyltryptamine (TRP) would provide benefits not possible when the alkaloid-containing foods were eaten alone. In Trial 1, four groups
P S Katz et al.
Journal of neurophysiology, 74(6), 2281-2294 (1995-12-01)
1. Neuromodulation has previously been shown to be intrinsic to the central pattern generator (CPG) circuit that generates the escape swim of the nudibranch mollusk Tritonia diomedea; the dorsal swim interneurons (DSIs) make conventional monosynaptic connections and evoke neuromodulatory effects
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