(1H-indol-3-ylmethyl)dimethylamine

• ChemBase ID: 72947
• Molecular Formular: C11H14N2
• Molecular Mass: 174.24226
• Monoisotopic Mass: 174.11569846
• SMILES: c12c(cccc1)[nH]cc2CN(C)C
• Canonical SMILES: CN(Cc1c[nH]c2c1cccc2)C
• InChI: InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
• InChIKey: OCDGBSUVYYVKQZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1H-indol-3-ylmethyl)dimethylamine
• IUPAC Traditional name: gramine
• Synonyms: Gramine; 3-(Dimethylaminomethyl)indole; β-Dimethylaminomethylindole; Donaxine; 3-(Dimethylaminomethyl)indole; NSC 16892; Gramine; 3-(二甲氨基甲基)吲哚; 芦竹碱

Database IDs

• CAS Number: 87-52-5
• EC Number: 201-749-8
• MDL Number: MFCD00005629
• Beilstein Number: 140521
• PubChem SID: 162037867; 24895037
• PubChem CID: 6890
• CHEMBL: 254348
• Chemspider ID: 6625
• KEGG ID: C08304
• Wikipedia Title: Gramine

CALCULATED PROPERTIES

• Acid pKa: 15.973409
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.3010347
• LogD (pH = 7.4): 0.14722463
• Log P: 2.0134046
• Molar Refractivity: 55.6872 cm^3
• Polarizability: 22.700798 Å^3
• Polar Surface Area: 19.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 132-134 °C(lit.); 132-134°C; 138-139 °C
• Flash Point: 167 °C; 332.6 °F

Safety Information

• Storage Condition: 0°C; -20°C
• RTECS: NL7525000
• German water hazard class: 3
• NFPA704:
  

  1

  2

  0

Product Information

• Purity: 95+%; 99%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C11H14N2

DETAILS

MP Biomedicals - 02101902

White powder
Intermediate for indole synthesis.

Selleck Chemicals - S2304

Research Area: Cancer
Biological Activity:
Gramine is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms. It is used mostly in synthetic organic chemistry as a starting material for tryptophan syntheses. [1]

Sigma Aldrich - G10806

Packaging
25 g in poly bottle
Application
Reactant for preparation of:
• Dopamine D2 receptor antagonists1
• Anti-malarial drugs2
• 5-indolyl-Mannich bases3
• Proliferation inhibitors4
• Inhibitors of human mast cell chymase5
• Preparation of DL-tryptophan6
• Potential detoxification inhibitors of the crucifer phytoalexin brassinin7
• 3-vinylindoles8
• Serotonin 5-HT6 receptor ligand templates9
• Selective protein kinase c delta (PKCδ) down regulators10

REFERENCES

• http://en.wikipedia.org/wiki/Gramine