A series of hexahydro[1,4]oxazino[3,4-a]isoquinolines as potential neuroleptics.
The synthesis and stereochemistry of trans-N,N-diethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro[1,4]oxazino[3,4-a]isoquinoline-3-carboxamide hydrochloride (16) and a series of analogues are described. 16 and its (+) isomer had neuroleptic properties in the Sidman avoidance test in gerbils. A few closely related amides of the trans series were active but cis amides were inactive as neuroleptics.
D000818:Animals; D014150:Antipsychotic Agents / Q000138:chemical synthesis*; D001362:Avoidance Learning / Q000187:drug effects; D003315:Cornea / Q000187:drug effects; D004924:Escape Reaction / Q000187:drug effects; D005849:Gerbillinae; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D008968:Molecular Conformation; D010078:Oxazines / Q000138:chemical synthesis / Q000494:pharmacology; D012018:Reflex / Q000187:drug effects
D014150:Antipsychotic Agents; D007546:Isoquinolines; D010078:Oxazines