1-[(5-Methoxy-3-indolylidene)methylamino]-2-pentylguanidine

Base Information

• Chemical Name: 1-[(5-Methoxy-3-indolylidene)methylamino]-2-pentylguanidine
• CAS No.: 145158-71-0
• Molecular Formula: C16H23N5O
• Molecular Weight: 301.392
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID6045955
• Wikidata: Q27088955,Q27166380
• NCI Thesaurus Code: C66583
• RXCUI: 139778
• Mol file: 145158-71-0.mol

Synonyms:5-methoxyindol-3-carboxaldehyde amino(pentylamino)methylenehydrazone hydrogen maleate;HTF 919;SDZ HTF 919;SDZ HTF-919;tegaserod;tegaserod maleate;Zelmac;Zelnorm

Chemical Property of 1-[(5-Methoxy-3-indolylidene)methylamino]-2-pentylguanidine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 2.15E-18mmHg at 25°C
• Melting Point: 155°
• Boiling Point: 470.556 °C at 760 mmHg
• PKA: 15.81±0.30(Predicted)
• Flash Point: 238.384 °C
• PSA: 159.89000
• Density: 1.189 g/cm³
• LogP: 3.40790
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 301.19026037
• Heavy Atom Count: 22
• Complexity: 385

Purity/Quality:

99% ^*data from raw suppliers

Tegaserod ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCN=C(N)NN=CC1=CNC2=C1C=C(C=C2)OC
• Uses: Treatment of gastrointestinal motility disorders (selective serotonin 5HT4antagonist).
• Indications: Tegaserod (Zelnorm) is serotonin-4 (5-HT4) receptor agonists that stimulate GI motility.
• Clinical Use: Tegaserod is being developed as a treatment for constipation- predominant irritable bowel syndrome (IBS). Within the first week, patients treated with tegaserod had significant improvements in abdominal pain and discomfort, constipation, and overall well-being. Efficacy was maintained throughout the treatment period. Tegaserod also demonstrated significant improvements in the three bowel-related assessments (stool frequency, stool consistency, and straining) within the first week, and these improvements were sustained throughout the treatment period. The most common adverse events reported thus far are headache and diarrhea.

Technology Process of 1-[(5-Methoxy-3-indolylidene)methylamino]-2-pentylguanidine

There total 2 articles about 1-[(5-Methoxy-3-indolylidene)methylamino]-2-pentylguanidine 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: 90.7%

5-methoxyindole-3-carboxaldehyde (10601-19-1) + N-amino-N'-pentylguanidine oxalate (1043452-36-3) → tegaserod (145158-71-0)

Guidance literature:

In water; for 2h; Heating / reflux;

Reference yield:

3-(5-methoxy-1H-indol-3-yl-methylene)-N-pentylcarbazimidamide hydrobromide (843609-64-3) → tegaserod (145158-71-0)

Guidance literature:

With sodium hydroxide; In methanol; Isopropyl acetate; water; at 15 - 20 ℃;

Reference yield: 70.2%

maleic acid (110-16-7,26099-09-2) + tegaserod (145158-71-0) → tegaserod maleate (189188-57-6)

Guidance literature:

In butanone; at 25 - 44 ℃; for 0.5 - 1h; Purification / work up;

upstream raw materials:

3-(5-methoxy-1H-indol-3-yl-methylene)-N-pentylcarbazimidamide hydrobromide

5-methoxyindole-3-carboxaldehyde

N-amino-N'-pentylguanidine oxalate

Downstream raw materials:

tegaserod maleate

2-[(5-methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide besylate

2-[(5-methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide benzoate

Refernces

• 1、 -. "STABLE MODIFICATIONS OF TEGASEROD HYDROGEN MALEATE". Page/Page column 10-11. . Retrieved 2010/02/10.