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M14870

Sigma-Aldrich

5-Methoxygramine

99%

Synonym(s):

3-(Dimethylaminomethyl)-5-methoxyindole, NSC 88885

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About This Item

Empirical Formula (Hill Notation):
C12H16N2O
CAS Number:
16620-52-3
Molecular Weight:
204.27
Beilstein:
170533
EC Number:
240-669-8
MDL number:
MFCD00005630
UNSPSC Code:
12352100
PubChem Substance ID:
24896649
NACRES:
NA.22

Assay

99%

mp

123-126 °C (lit.)

SMILES string

COc1ccc2[nH]cc(CN(C)C)c2c1

InChI

1S/C12H16N2O/c1-14(2)8-9-7-13-12-5-4-10(15-3)6-11(9)12/h4-7,13H,8H2,1-3H3

InChI key

GOERTRUXQHDLHC-UHFFFAOYSA-N

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Application

  • Reactant for preparation of dopamine D2 receptor antagonists
  • Reactant for asymmetric preparation of ethenyl(tetrahydro)carbazoledicarboxylates via gold(I)-catalyzed intramolecular Friedel-Crafts allylic alkylation reaction
  • Reactant for preparation of N-substituted 3-aryl-8-azabicyclo[3.2.1]octan-3-ols as dopamine D2-like receptor ligands
  • Reactant for preparation of substituted N-trimethoxybenzoyl indoles, indolines, and a tetrahydroquinoline via N-aroylation with trimethoxybenzoyl chloride or anhydride as antitubulin agents
  • Reactant for preparation of indolylmethanesulfonamide and its methoxy derivatives

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ2545
MKAA0713
S63967
S35234
10207AB

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B M Clancy et al.
The Journal of pharmacology and experimental therapeutics, 242(1), 108-114 (1987-07-01)
The kinetics of agonist and antagonist interactions with the 5-hydroxytryptamine2 receptor were studied in the isolated rabbit aorta by following the antagonist-induced decrease in the steady-state response to an agonist. A model describing the competitive drug-receptor interactions was fitted to
Mark G Devlin et al.
European journal of pharmacology, 498(1-3), 59-69 (2004-09-15)
The effect of ligand pretreatment on human 5-hydroxytryptamine2C (5-HT2C) receptors was examined in CHO cells expressing high (CHO-1C7; 67+/-3 pmol/mg) or low (CHO-1C19; 72+/-10 fmol/mg) levels of the receptor. Seventy-two hours pretreatment of CHO-1C7 cells with various ligands did not

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