Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
Bartleby Related Questions Icon

Related questions

Question

Propose a reagent for the conversion of (G) to racemethorphan

The analgesic, soporific, and euphoriant properties of the dried juice obtained from unripe
seed pods of the opium poppy Papaver somniferum have been known for centuries. By the
beginning of the nineteenth century, the active principle, morphine, had been isolated
and its structure determined. Even though morphine is one of modern medicine's most
effective painkillers, it has two serious disadvantages. First, it is addictive. Second, it
depresses the respiratory control center of the central nervous system. Large doses of
morphine (or heroin, which is the 3,6-diacetyl ester of morphine) can lead to death by
respiratory failure.
Me.
H
Me.
OH
MeO
Morphine
Morphinan
(+/-) = Racemethorphan
(+) = Dextromethorphan
(-) = Levomethorphan
%3D
%3D
For these reasons, chemists have sought to produce painkillers related in structure
to morphine, but without the serious disadvantages. One strategy has been to mod-
ify the carbon-nitrogen skeleton of morphine in the hope of producing medications
equally effective but with reduced side effects. One target of this synthetic effort
was morphinan, the bare morphine skeleton. Among the compounds thus synthe-
sized, racemethorphan (the racemic mixture) and levomethorphan (the levorotatory
enantiomer) proved to be very potent analgesics. Interestingly, the dextrorotatory
enantiomer, dextromethorphan, has no analgesic activity. It does, however, show
approximately the same antitussive (cough-suppressing) activity as morphine and is
therefore used extensively in cough remedies.
Following is a synthesis of racemethorphan.
expand button
Transcribed Image Text:The analgesic, soporific, and euphoriant properties of the dried juice obtained from unripe seed pods of the opium poppy Papaver somniferum have been known for centuries. By the beginning of the nineteenth century, the active principle, morphine, had been isolated and its structure determined. Even though morphine is one of modern medicine's most effective painkillers, it has two serious disadvantages. First, it is addictive. Second, it depresses the respiratory control center of the central nervous system. Large doses of morphine (or heroin, which is the 3,6-diacetyl ester of morphine) can lead to death by respiratory failure. Me. H Me. OH MeO Morphine Morphinan (+/-) = Racemethorphan (+) = Dextromethorphan (-) = Levomethorphan %3D %3D For these reasons, chemists have sought to produce painkillers related in structure to morphine, but without the serious disadvantages. One strategy has been to mod- ify the carbon-nitrogen skeleton of morphine in the hope of producing medications equally effective but with reduced side effects. One target of this synthetic effort was morphinan, the bare morphine skeleton. Among the compounds thus synthe- sized, racemethorphan (the racemic mixture) and levomethorphan (the levorotatory enantiomer) proved to be very potent analgesics. Interestingly, the dextrorotatory enantiomer, dextromethorphan, has no analgesic activity. It does, however, show approximately the same antitussive (cough-suppressing) activity as morphine and is therefore used extensively in cough remedies. Following is a synthesis of racemethorphan.
H
NC
H,N-
H,PO,
Meo
(A)
(B)
(C)
H
NaBH,
(redraw)
H,PO,
MeO
MeO
MeO
(D)
(E)
H,C
EtO
MeO
MeO
MeO
(F)
(G)
Racemethorphan
expand button
Transcribed Image Text:H NC H,N- H,PO, Meo (A) (B) (C) H NaBH, (redraw) H,PO, MeO MeO MeO (D) (E) H,C EtO MeO MeO MeO (F) (G) Racemethorphan
Expert Solution
Check Mark
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY