G10806
Gramine
97.5%
Synonym(s):
3-(Dimethylaminomethyl)indole, Donaxine, NSC 16892
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C11H14N2
CAS Number:
Molecular Weight:
174.24
Beilstein:
140521
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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S Iwata et al.
European journal of pharmacology, 432(1), 63-70 (2001-12-06)
We examined the effects of 2,5,6-tribromo-1-methylgramine (TBG), isolated from bryozoan, and its derivative, 5,6-dibromo-1,2-dimethylgramine (DBG), on the contraction of rat aorta. TBG and DBG decreased the high-K(+)-induced increase in muscle contraction and cytosolic Ca(2+) level ([Ca(2+)](i)), respectively. The inhibitory effects
N Nakahata et al.
European journal of pharmacology, 382(2), 129-132 (1999-10-21)
5,6-Dibromo-1,2-dimethylgramine evoked Ca(2+) release from skeletal muscle sarcoplasmic reticulum through ryanodine receptors in a concentration-dependent manner with an EC(50) of 22.2 microM. Since the EC(50) of caffeine was 0.885 mM, 5,6-dibromo-1,2-dimethylgramine was 40 times more sensitive than caffeine. Among 14
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
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
P Mayser et al.
Mycoses, 47(1-2), 34-39 (2004-03-05)
Reference as well as field strains of Malassezia furfur (30), M. sympodialis (49), M. globosa (52), M. obtusa (one), M. restricta (one), M. slooffiae (seven), and M. pachydermatis (373) were investigated for their ability to produce pigment and fluorochromes when
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