Homework Help is Here – Start Your Trial Now!
Science
Chemistry
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
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
See similar textbooks
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.
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
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
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Ammonium Salts
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.
Similar questions
Recommended textbooks for you
Organic Chemistry
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
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
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning
Chemistry for Today: General, Organic, and Bioche…
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 & Chemical Reactivity
Chemistry
ISBN:
9781133949640
Author:
John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:
Cengage Learning
Chemistry & Chemical Reactivity
Chemistry & Chemical Reactivity
Chemistry
ISBN:
9781337399074
Author:
John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:
Cengage Learning
SEE MORE TEXTBOOKS