Rice K C, Jacobson A E
J Med Chem. 1975 Oct;18(10):1033-5. doi: 10.1021/jm00244a019.
3,6-Diacetylnormorphine (norheroin) and 6-acetylnormorphine have been prepared in excellent yield through the 3,N-bis(tert-butoxycarbonyl) derivative of normorphine via acetylation and selective removal of protecting groups. This general procedure would be applicable to the preparation of various 3,6-diesters or 6-monoesters of normorphine. The analgesic potency of norheroin was found to be the same as that of 6-acetylnormorphine, about 0.05 that of heroin. The onset, peak, and duration of action of these compounds were nearly identical and comparable with morphine.
通过吗啡的3,N-双(叔丁氧羰基)衍生物经乙酰化和保护基团的选择性去除，已以优异的产率制备出3,6-二乙酰基吗啡（去甲海洛因）和6-乙酰基吗啡。这一通用方法适用于制备吗啡的各种3,6-二酯或6-单酯。发现去甲海洛因的镇痛效力与6-乙酰基吗啡相同，约为海洛因的0.05倍。这些化合物的起效时间、峰值和作用持续时间几乎相同，且与吗啡相当。
