Clarke F H, Hill R T, Koo J, Lopano R M, Maseda M A, Smith M, Soled S, VonVeh G, Vlattas I
J Med Chem. 1978 Aug;21(8):785-91. doi: 10.1021/jm00206a013.
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.
