Didesmethyl sumatriptan

Base Information

• Chemical Name: Didesmethyl sumatriptan
• CAS No.: 88919-22-6
• Molecular Formula: C12H17 N3 O2 S
• Molecular Weight: 267.352
• Hs Code.: 2935009090
• European Community (EC) Number: 618-221-1
• UNII: WE0Q003U63
• DSSTox Substance ID: DTXSID90237424
• Wikidata: Q27292582
• Mol file: 88919-22-6.mol

Synonyms:88919-22-6;3-(2-Aminoethyl)-N-methyl-1H-indole-5-methanesulfonamide;Didesmethyl sumatriptan;1-(3-(2-Aminoethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide;1-[3-(2-aminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide;1H-Indole-5-methanesulfonamide, 3-(2-aminoethyl)-N-methyl-;UNII-WE0Q003U63;WE0Q003U63;(3-(2-(Aminoethyl))-1H-indol-5-yl)-N-methylmethanesulfonamide;(3-(2-Aminoethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide;Sumatriptan succinate specified impurity E [EP];3-(2-Aminoethyl)-N-methyl-1H-indole-5-methanesulfonamide (Didesmethyl Sumatriptan);[3-(2-Aminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide;Sumatriptan impurity, (3-(2-(aminoethyl))-1H-indol-5-yl)-N-methylmethanesulfonamide- [USP];Sumatriptan succinate impurity, (3-(2-(aminoethyl))-1H-indol-5-yl)-N-methylmethanesulfonamide- [USP];Sumatriptan EP Impurity E;SCHEMBL5918470;DTXSID90237424;MURZXKIEJFJMPP-UHFFFAOYSA-N;MFCD08063851;STL018673;AKOS015920454;CS-O-08214;AS-18598;FT-0659227;A843003;Q27292582;SUMATRIPTAN SUCCINATE IMPURITY E [EP IMPURITY];[3-(2-aminoethyl)-1h-indol-5-yl]-n-methylmethanesulphonamide;3-(2-aminoethyl)-1H-indole-5-yl-N-methyl methane sulphonamide;3-[2-Amino ethyl]-N-Methyl-1H-Indole-5-Methane Sulfonamide;SUMATRIPTAN IMPURITY, (3-(2-(AMINOETHYL))-1H-INDOL-5-YL)-N-METHYLMETHANESULFONAMIDE- [USP IMPURITY];SUMATRIPTAN SUCCINATE IMPURITY, (3-(2-(AMINOETHYL))-1H-INDOL-5-YL)-N-METHYLMETHANESULFONAMIDE- [USP IMPURITY]

Chemical Property of Didesmethyl sumatriptan

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 151-154°C
• Refractive Index: 1.65
• Boiling Point: 523.772°C at 760 mmHg
• PKA: 11.30±0.40(Predicted)
• Flash Point: 270.568°C
• PSA: 96.36000
• Density: 1.394g/cm³
• LogP: 2.89030
• Storage Temp.: Refrigerator
• Solubility.: Acetonitrile (Slightly, Heated), Methanol (Slightly)
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 267.10414797
• Heavy Atom Count: 18
• Complexity: 366

Purity/Quality:

97% ^*data from raw suppliers

3-(2-Aminoethyl)-N-methyl-1H-indole-5-methanesulfonamide(DidesmethylSumatriptan) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCN
• Uses: An antimigraine agent. A Sumatriptan intermediate 3-(2-Aminoethyl)-N-methyl-1H-indole-5-methanesulfonamide (Didesmethyl Sumatriptan) (Sumatriptan EP Impurity E) is an antimigraine agent. A Sumatriptan intermediate.

Technology Process of Didesmethyl sumatriptan

There total 3 articles about Didesmethyl sumatriptan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

4-aminobutyrylaldehyde diethylacetal (6346-09-4) + 4-hydrazinobenzyl methyl sulfone (139272-29-0) → 3-(2-aminoethyl)-1H-indole-5-yl-N-methyl methane sulphonamide (88919-22-6)

Guidance literature:

4-aminobutyrylaldehyde diethylacetal; 4-hydrazinobenzyl methyl sulfone; With hydrogenchloride; In water; at 90 ℃; for 1h;

With sodium hydroxide; In water; pH=7;

Reference yield:

aqueous potassium carbonate + 3-(Cyanomethyl)-N-methyl-1H-indole-5-methanesulphonamide (88918-76-7) → 3-(2-aminoethyl)-1H-indole-5-yl-N-methyl methane sulphonamide (88919-22-6)

Guidance literature:

In tetrahydrofuran; ethyl acetate;

Reference yield:

→ 3-(2-aminoethyl)-1H-indole-5-yl-N-methyl methane sulphonamide (88919-22-6)

Guidance literature:

upstream raw materials:

3-(Cyanomethyl)-N-methyl-1H-indole-5-methanesulphonamide

4-aminobutyrylaldehyde diethylacetal

4-hydrazinobenzyl methyl sulfone

Downstream raw materials:

sumatripan

3-(Cyanomethyl)-N-methyl-1H-indole-5-methanesulphonamide