[(5-methoxy-1H-indol-3-yl)methyl]dimethylamine

• ChemBase ID: 92255
• Molecular Formular: C12H16N2O
• Molecular Mass: 204.26824
• Monoisotopic Mass: 204.12626314
• SMILES: [nH]1c2c(cc(cc2)OC)c(c1)CN(C)C
• Canonical SMILES: COc1ccc2c(c1)c(c[nH]2)CN(C)C
• InChI: 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
• InChIKey: GOERTRUXQHDLHC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(5-methoxy-1H-indol-3-yl)methyl]dimethylamine
• IUPAC Traditional name: methoxygramine
• Synonyms: 5-METHOXYGRAMINE; NSC 88885; 3-(Dimethylaminomethyl)-5-methoxyindole; 5-Methoxygramine; N-[(5-methoxy-1H-indol-3-yl)methyl]-N,N-dimethylamine; 5-Methoxygramine; N,N-Dimethyl-(5-methoxy-1H-indol-3-yl)methylamine; 3-[(Dimethylamino)methyl]-5-methoxy-1H-indole; 5-甲氧基-3-二甲胺基甲基吲哚; 5-甲氧基芦竹碱

Database IDs

• CAS Number: 16620-52-3
• EC Number: 240-669-8
• MDL Number: MFCD00005630
• Beilstein Number: 170533
• PubChem SID: 162078953; 24896649
• PubChem CID: 27965

CALCULATED PROPERTIES

• Acid pKa: 16.30199
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.4481684
• LogD (pH = 7.4): 0.017971225
• Log P: 1.8557333
• Molar Refractivity: 62.1504 cm^3
• Polarizability: 25.15151 Å^3
• Polar Surface Area: 28.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 122-123°C; 123-126 °C(lit.)

Safety Information

• Storage Warning: Irritant
• RTECS: NL7700000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%; 99%
• Empirical Formula (Hill Notation): C12H16N2O
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05210540

MP Biomedicals Rare Chemical collection

Sigma Aldrich - M14870

Packaging
1, 5 g in glass bottle
Application

• Reactant for preparation of dopamine D2 receptor antagonists1
• Reactant for asymmetric preparation of ethenyl(tetrahydro)carbazoledicarboxylates via gold(I)-catalyzed intramolecular Friedel-Crafts allylic alkylation reaction2
• Reactant for preparation of N-substituted 3-aryl-8-azabicyclo[3.2.1]octan-3-ols as dopamine D2-like receptor ligands3
• Reactant for preparation of substituted N-trimethoxybenzoyl indoles, indolines, and a tetrahydroquinoline via N-aroylation with trimethoxybenzoyl chloride or anhydride as antitubulin agents4
• Reactant for preparation of indolylmethanesulfonamide and its methoxy derivatives5