Optical isomers of 2-(2-ethoxyphenoxymethyl)tetrahydro-1,4-oxazine (viloxazine) and related compounds.
The optical isomers of 2-(2-ethoxyphenoxymethyl)tetrahydro-1,4-oxazine (viloxazine) and 2-(3-methoxyphenoxymethyl)tetrahydro-1,4-oxazine have been prepared and absolute configurations have been assigned. In their action on the central nervous system the S isomers are at least ten times more potent than the R isomers. The intermediate 4-benzyl-2-(p-toluensulfonyloxymethyl)tetrahydro-1,4-oxazine has been resolved. Its isomers provide a convenient starting point for the preparation of optical isomers of viloxazine analogues of known configuration.
D000818:Animals; D001831:Body Temperature / Q000187:drug effects; D009043:Motor Activity / Q000187:drug effects; D009904:Optical Rotation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship