Minor alterations of the chemical structure of the more familiar drugs often produce compounds with unusual and, in some cases, paradoxical effects. Since the late 19th century the morphine radical has been modified repeatedly by different workers. Some of the more familiar products of this alteration are apomorphine, heroin, ethylmorphine hydrochloride ("dionin"), and dihydro-morphinone (dilaudid®) hydrochloride. In 1941 a compound was prepared differing from morphine only by the substitution of an allyl for the methyl group in the heterocyciic ring. This compound, N-allylnormorphine ("nalline"), was investigated by Unna in 1943 and found to be an almost complete antagonist to the sedative, anal-gesic, and respiratory depressant action of morphine. Unna's work has been extended by other investigators who have shown that N-allylnormorphine is equally effective in antagonizing the effects of meperidine hydrochloride, methadone hydrochloride, codeine, and dihydromorphinone.
There have been few reports to date on the use of N-allylnormorphine in methorphinan
Bornstein M, Yorburg L, Johnston B. N-ALLYLNORMORPHINE IN TREATMENT OF METHORPHINAN (DROMORANA®) HYDRO-BROMIDE POISONING. JAMA. 1953;151(11):908–910. doi:10.1001/jama.1953.02940110030008
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