Xanomeline

Base Information

• Chemical Name: Xanomeline
• CAS No.: 131986-45-3
• Molecular Formula: C₁₄H₂₃N₃OS
• Molecular Weight: 281.422
• Hs Code.: 2934999090
• European Community (EC) Number: 683-413-4
• UNII: 9ORI6L73CJ
• DSSTox Substance ID: DTXSID60157286
• Nikkaji Number: J489.337I
• Wikipedia: Xanomeline
• Wikidata: Q8042940
• NCI Thesaurus Code: C152926
• Pharos Ligand ID: WZGZ1YTXFSVX
• Metabolomics Workbench ID: 53519
• ChEMBL ID: CHEMBL21536
• Mol file: 131986-45-3.mol

Synonyms:(3-O-hexyloxy)-TZTP;3-(3-O-hexyl-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine;LY 246708;LY-246708;LY246708;xanomeline;xanomeline tartrate

Chemical Property of Xanomeline

Chemical Property:

• Vapor Pressure: 1.64E-06mmHg at 25°C
• Refractive Index: 1.537
• Boiling Point: 397 °C at 760 mmHg
• PKA: 7.34±0.40(Predicted)
• Flash Point: 193.9 °C
• PSA: 66.49000
• Density: 1.101 g/cm³
• LogP: 3.15400
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble10mg/mL, clear (warmed)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 281.15618354
• Heavy Atom Count: 19
• Complexity: 298

Purity/Quality:

99.3% ^*data from raw suppliers

3-(Hexyloxy)-4-(1-Methyl-1,2,5,6-Tetrahydropyridin-3-Yl)-1,2,5-Thiadiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCOC1=NSN=C1C2=CCCN(C2)C
• Uses: Alzheimer’s disease treatment (cholinergic agonist).

Technology Process of Xanomeline

There total 9 articles about Xanomeline 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: 75.0%

3-(3-Pentyloxy-1,2,5-thiadiazol-4-yl)-1-methylpyridinium iodide (131988-16-4) → xanomeline (131986-45-3)

Guidance literature:

With methanol; sodium tetrahydroborate; at 20 ℃;

DOI:10.1016/j.bioorg.2020.103633

Reference yield: 60.0%

3-(3-Chloro-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine (131986-59-9) + hexan-1-ol (111-27-3) → xanomeline (131986-45-3)

Guidance literature:

hexan-1-ol; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

3-(3-Chloro-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine; In tetrahydrofuran; Reflux;

DOI:10.1139/V10-149

Reference yield:

3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide (131988-19-7) → xanomeline (131986-45-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -10 ℃; for 1h;

DOI:10.1021/jm00090a019

upstream raw materials:

3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide

3-(3-Chloro-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine

hexan-1-ol

3-pyridinecarboxaldehyde

Refernces

• 1、 Van Oosten, Erik M.,Wilson, Alan A.,Mamo, David C.,Pollock, Bruce G.,Mulsant, Benoit H.,Houle, Sylvain,Vasdev, Neil. "Towards the development of new subtype-specific muscarinic receptor radiopharmaceuticals - Radiosynthesis and ex vivo biodistribution of [ 18F]3-(4-(2-(2-(2-fluoroethoxy)ethoxy)ethylthio)-1,2, 5-thiadiazol-3-yl)-1-methyl-1,2,5,6-tetrahydropyrid". experimental part. p. 1222 - 1232. Retrieved 2011/02/24.
• 2、 -. "Combination therapy for treatment of psychoses". . . Retrieved 2008/06/13.