A-Phenylindole

Sertindole is one of the newer antipsychotic medications available. It is classified chemically as a phenylindole derivative and has activity at dopamine and serotonin receptors. It is not associated with sedative effects. Sertindole was voluntarily withdrawn from the market late 1998 due to concerns over the risk of cardiac arrhythmia s. The European Commission recommended lifting the marketing restrictions on sertindole in 2005 with a regulatory requirement of ECG monitoring. 

A clue to a possible a-phenylindole origin of these compounds was recently provided by the isolation of trikentramine (104) from the Senegalese sponge Trikentrion loeve (102). 

Diphenylliodonium salts react with amines in the presence of a copper catalyst. Diphenyliodonium tetrafluoroborate, Ph2l+BF4, reacts with indole in DMF at 150°C with a Cu(OAc)2 catalyst, for example, to give A-phenylindole. ... 

BIMU 8 is a benzimidazole-carboxamide derivative, a selective (5-HT4-subtype) 5-hydroxytryptamine receptor AGONIST. It has experimental GASTRIC motility stimulant (gastroprokinetic) activity used as a pharmacological tool, binedaline [inn] (Scha 1659) is a phenylindole, a noradrenaline uptake inhibitor and antidepressant. Never marketed. 

Owing to metal chlorides titration by the coulometric method, and carboxylic acid titration by the potentiometric method, it is possible to follow the metal soaps consumption during thermomechanical heat treatments. This new technique provides a better understanding of the stabilization mechanisms of PVC with the calciumr-zinc system, and offers a better explanation of synergistic effects between metal soaps and secondary stabilizers such as epoxidized soya-bean oil, a-phenylindole, and butanediol-p-aminocroto-nate. The influence of these last stabilizers on zinc chloride formation enables us to classify them into short- and longterm stabilizers. 

To study the influence of secondary stabilizers on zinc chloride formation, we have prepared PVC sheets on a rolling mill with the different binary mixtures zinc stearate and a-phenylindole, epoxidized soya-bean oil, or /3-aminocrotonate esters, and we have followed the zinc chloride formation by coulometric titration of chloride ions. In Figure 5 we have combined the percentage of zinc chloride that may be liberated with respect to the initial amount of zinc stearate in the presence of a-phenyl-indole (Curve 1 )> epoxidized soya-bean oil (Curves 2 and 3), and butane-diol- -aminocrotonate (Curve 4) during heating in a stove at 180°C. 

These results show that a-phenylindole does not influence zinc chloride formation and that it may catalyze the substitution reaction of allylic chlorine atoms on the polymer as it catalyzes the esterification reaction of 4-chloro-2-hexene (6). But its accumulation quickly implies discoloration. From these experiments, it is clear that a-phenylindole is a shortterm stabilizer that only impedes initial coloring. Nevertheless, the darkening develops as quickly as the cross-linking. These results account also for Ta variations, implying that the time prior to cross-linking is not very... 

CAS 948-65-2 EINECS/ELINCS 213-436-3 Synonyms IH-Indole, 2-phenyl- Indole, 2-phenyl- 2-Phenyl-1H-indole a-Phenylindole... 

Of the heterocyclic nitrogen-containing compounds, a-phenylindole is used to stabilize latex polymers and copolymers of vinyl chloride [99]. Melamine has foimd use for the stabilizing of suspension polymers, where a-phenylindole proves inactive [63]. Derivatives of morpholine [274], symmetrical triazine [275], pyrazole [276], as well as derivatives of imidazole, imidazoline, oxazole, oxazoline, thiazole, and thiazoline [277] are recommended in the patent literature for stabilization. 

These stabilizers are also called secondary stabilizers and they comprise epoxides, organic phosphites, antioxidants, a-phenylindole, urea derivatives, and 3-aminocrotonic acid esters. 

Typical thermal stabilizers for PVC are organic metal salts and soaps, phosphite, esters, and epoxy compounds. Examples are barium/zinc carboxylates [46], barium/cadmium carboxy-lates [47], calcium/zinc stearate [48], lead stearate [49],organotinmercaptides[50],organotin sulfides, organotin carboxylates[51], among others. Costabilizers such as 1,3-diketones, dihydropyridines, epoxy plasticizers, P-ketocarboxylic acid esters, phenolic antioxidants, a-phenylindols, and phosphates are used to improve the stabilizer s elfectiveness. 

---