Esters of 4-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]-1-piperazieneethanol and related compounds as long-acting antipsychotic agents. Synthesis of the 1-adamantoate, the first crystalline base.
A number of new esters of fluphenazine are described: among these was the 1-adamantoate, 1h, the first highly crystalline ester of that drug. The 1-adamantoate of pipotiazine, 2b, typically, was an oil. Following a single subcutaneous or intramuscular injection of 25 mg/kg of either 1h or 2b, dissolved in sesame oil, each ester was found to be a potent and long-acting inhibitor of conditioned avoidance behavior in the rat.
D000218:Adamantane / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D014150:Antipsychotic Agents / Q000138:chemical synthesis*; D001362:Avoidance Learning / Q000187:drug effects; D003460:Crystallization; D003692:Delayed-Action Preparations; D005260:Female; D005476:Fluphenazine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D010640:Phenothiazines / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D051381:Rats; D011930:Reaction Time / Q000187:drug effects
D014150:Antipsychotic Agents; D003692:Delayed-Action Preparations; D010640:Phenothiazines; D000218:Adamantane; D005476:Fluphenazine