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
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
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.58P
Related questions
Question
Propose a reagent for the conversion of (G) to racemethorphan
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 2 images
Knowledge Booster
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
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning
Chemistry for Today: General, Organic, and Bioche…
Chemistry
ISBN:
9781305960060
Author:
Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:
Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:
9781133949640
Author:
John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:
Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:
9781337399074
Author:
John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:
Cengage Learning