334981-08-7

Basic information

• Product Name: 5-HydroxyMethyl-N,N-diMethyltryptaMine
• Synonyms: 5-HydroxyMethyl-N,N-diMethyltryptaMine;3-[2-(DiMethylaMino)ethyl]-1H-Indole-5-Methanol
• CAS NO: 334981-08-7
• Molecular Formula: C13H17N2O
• Molecular Weight: 217.28688
• Product Categories: Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 334981-08-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 412.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.156±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 14.54±0.10(Predicted)
• CAS DataBase Reference: 5-HydroxyMethyl-N,N-diMethyltryptaMine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HydroxyMethyl-N,N-diMethyltryptaMine(334981-08-7)
• EPA Substance Registry System: 5-HydroxyMethyl-N,N-diMethyltryptaMine(334981-08-7)

Safety Data

• Hazardous Substances Data: 334981-08-7(Hazardous Substances Data)

Usage

Uses

Degradation product of Sumatriptan Succinate (S810000).

Upstream product

• 103628-46-2 sumatripan 
• 152673-51-3 3-[2-(Dimethylamino)ethyl]-1H-indole-5-carboxaldehyde 
• 545338-88-3 ethyl 3-(2-chloroethyl)-5-indolecarboxylate 
• 14685-90-6 4-ethoxycarbonylphenylhydrazine 
• 94-09-7 p-aminoethylbenzoate 
• 137499-21-9 ethyl 3-[2-(dimethylamino)ethyl]-5-indolecarboxylate 

Downstream Products

• 545338-89-4 [[3-[2-(dimethylamino)ethyl]-2-[[3-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1H-indol-5-yl]-N-methylmethanesulfonamide 

Relevant articles and documents

Identification and characterization of stress degradation products of sumatriptan succinate by using LC/Q-TOF-ESI-MS/MS and NMR: Toxicity evaluation of degradation products

Sumatriptan succinate, a selective 5-HT1B receptor agonist, was subjected to forced degradation studies as per to International Conference on Harmonization-specified conditions. The drug exclusively showed its degradation under basic, photolytic, and oxidative stress conditions, whereas it was found to be stable under acidic, thermal, and neutral conditions. Eight (DP-1 to DP-8) degradation products were identified and characterized by UPLC-ESI/MS/MS experiments combined with accurate mass measurements. The effective chromatographic separation was achieved on Hibar Purospher STAR, C18 (250?×?4.6?mm, 5?μm) column using mobile phase consisting of 0.1% formic acid and methanol at a flow rate of 0.6?mL/minute in gradient elution method. It is noteworthy that 2 major degradation products DP-3 and DP-7 were isolated using preparative HPLC and characterized by advanced NMR experiments. The degradation pathway of the sumatriptan was established, which was duly justified by mechanistic explanation. In vitro cytotoxicity of isolated DPs was tested on normal human cells such as HEK 293 (embryonic kidney cells) and RWPE-1 (normal prostate epithelial cells). This study revealed that they were nontoxic up to 100?μm concentration. Further, in silico toxicity of the drug and its degradation products was determined using ProTox-II prediction tool. This study revealed that DP-4 and DP-8 are predicted for immune toxicity. Amine oxidase A and prostaglandin G/H synthase 1 are predicted as toxicity targets for DP-3, DP-4, and DP-6 whereas DP-1 and DP-2 are predicted for amine oxidase A target.

Synthesis of [3-[2-(dimethylamino)ethyl]-2-[[3-(dimethylamino)ethyl]-1H-indol-5-yl] methyl]-1H-indol-5-yl]-N-methylmethanesulfonamide - The main sumatriptane impurity

Alkylation of sumatriptane in position 2 by 3-[2-(dimethylamino)ethyl]-5-indolemethanol has been described. Alternative multistep synthesis of 3-[2-(dimethylamino)ethyl]-5-indolemethanol has been presented.