(+)- and (-)-3-Methoxycyproheptadine. A comparative evaluation of the antiserotonin, antihistaminic, anticholinergic, and orexigenic properties with cyproheptadine

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Abstract
The synthesis and resolution of (.+-.)-3-methoxycyproheptadine [(.+-.)-4] are described. As a peripheral serotonin antagonist [rat], (.+-.)-4 was 1/2 as potent as cyproheptadine (1b). The peripheral anticholinergic [mouse] and antihistaminic [guinea pig] activities as well as the orexigenic property of (.+-.)-4 are less than those of 1b. A further comparison of the enantiomers (+)-4 and (-)-4 shows that all of the anticholinergic activity of (.+-.)-4 resides solely in the dextrorotatory enantiomer, (+)-4 while the antiserotonin activity, which is similar to that of 1b, resides in the levorotatory enantiomer, (-)-4. Antihistaminic and orexigenic [cat] activity also resides in (-)-4 but these properties are reduced compared to those of 1b.