Remy D C, Rittle K E, Hunt C A, Anderson P S, Engelhardt E L, Clineschmidt B V, Scriabine A
J Med Chem. 1977 Dec;20(12):1681-4. doi: 10.1021/jm00222a031.
The synthesis and resolution of (+/-)-3-methoxycyproheptadine [(+/-)-4] are described. As a peripheral serotonin antagonist, (+/-)-4 was found to be one-half as potent as cyproheptadine (1b). The peripheral anticholinergic and antihistaminic 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 activity also resides in (-)-4 but these properties are reduced compared to those of 1b.
描述了(+/-)-3-甲氧基赛庚啶[(+/-)-4]的合成与拆分。作为一种外周5-羟色胺拮抗剂，发现(+/-)-4的效力是赛庚啶(1b)的一半。(+/-)-4的外周抗胆碱能和抗组胺活性以及促食欲特性均低于1b。对映体(+)-4和(-)-4的进一步比较表明，(+/-)-4的所有抗胆碱能活性仅存在于右旋对映体(+)-4中，而与1b相似的抗5-羟色胺活性则存在于左旋对映体(-)-4中。抗组胺和促食欲活性也存在于(-)-4中，但与1b相比，这些特性有所降低。
