tazomeline tazomeline tazomeline (ly-287,041) is a drug which acts as a non-selective muscarinic acetylcholine receptor agonist. it was in clinical trials for the treatment of cognitive dysfunction such as that seen in alzheimer's disease and schizophrenia, but development was apparently scrapped for unknown reasons. another of the patented uses is for the treatment of "severe painful conditions". tazomelineclinical dataatc codenoneidentifiers iupac name 5--1-methyl-1,2,3,6-tetrahydropyridine cas number131987-54-7pubchem cid131460chemspider116193uniiqdp6s14w5wchemblchembl131819comptox dashboard (epa)dtxsid80157288 chemical and physical dataformulac14h23n3s2molar mass297.48 g·mol−13d model (jsmol)interactive image smiles n2snc(/c1=c/ccn(c)c1)c2scccccc synthesis synthesis: patent: precursor (xxxv): ex 1: a strecker type alpha-amino nitrile between nicotinaldehyde, potassium cyanide and ammonium chloride gives amino(pyridin-3-yl)acetonitrile (2). the halogenation of this intermediate with sulfur monochloride in dmf led to 3-chloro-4-(3-pyridyl)-1,2,5-thiadiazole (3). ex 64: thioether formation with 1-hexanethiol (4) in the presence of sodium hydrogen sulfide, dmf and k2co3 gave 3-(4-hexylthio-1,2,5-thiadiazol-3-yl)pyridine, cid:10755149 (5). alkylation with methyl iodide gives 3-(4-hexylthio-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide, cid:19075299 (6). the reduction of the pyridine with sodium borohydride in alcohol gives the tetrahydropyridine and hence completed the synthesis of tazomeline (7).