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NALORPHINE (N-ALLYLNORMORPHINE)Practical and Theoretical Considerations
LOUIS LASAGNA, M.D.
AMA Arch Intern Med. 1954;94(4):532-558.
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HISTORY
THE HISTORY of N-substituted allyl compounds of the morphine series is both fascinating and instructive. Pohl,1 almost 40 years ago, became interested in the work of a colleague named Piazza. The latter worker had found allyl compounds to be, in general, irritating to tissues and (under some circumstances) productive of stimulant effects on the respiration. Pohl reasoned that this "stimulant" or "irritant" effect might be "directed towards the central nervous system" by incorporating an allyl group into the opium alkaloids. He accordingly experimented with O-allylnormorphine and N-allylnorcodeine. Investigations in rabbits revealed that the latter drug, while essentially inactive per se, would antagonize the respiratory depression of morphine in rabbit and dog. For over 25 years this exciting fact Structural formula of morphine and of nalorphine (N-allylnormorphine). lay buried in the literature. In 1941, McCawley, Hart, and Marsh2 synthetized what they thought to be N-allylnormorphine (Figure), in a
. . . [Full Text PDF of this Article]
Author Affiliations
BOSTON
From the Anesthesia Laboratory of the Harvard Medical School, at the Massachusetts General Hospital.
Footnotes
This work was supported in part by a grant from the Medical Research and Development Board of the United States Army, Contract No. DA-49-007-MD-92 (made to Dr. H. K. Beecher), and in part by a grant awarded by the Committee on Drug Addiction and Narcotics, National Research Council, from funds contributed by a group of interested pharmaceutical manufacturers.
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