но NH OH A H. Ergotamine Lysergic acid diethylamide of

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
icon
Concept explainers
Question

Reagents and mechanism please 

This is a reaction pathway depicting the synthesis of Lysergic acid diethylamide (LSD) from Ergotamine.

1. **Ergotamine Structure:**
   - The chemical structure on the far left is Ergotamine, a complex molecule containing a bicyclic hexahydroindole ring system fused with a lysergic acid moiety.

2. **Transformation A:**
   - The first arrow labeled "A" indicates the initial transformation where Ergotamine undergoes a reaction to form an intermediary compound. This involves modifying the side chain while retaining the indole and hexahydroindole ring systems.

3. **Transformation B:**
   - The second arrow labeled "B" represents the conversion of the intermediate compound to another structure, showing the replacement of a hydroxyl group with a chlorine atom, and the retention of the core bicyclic structure.

4. **Transformation C:**
   - The final step, labeled "C", involves the transformation to Lysergic acid diethylamide (LSD), characterized by the addition of a diethylamide group.

5. **Lysergic Acid Diethylamide (LSD) Structure:**
   - The final structure on the far right is LSD, featuring a core lysergic acid structure with a diethylamide functional group.

This pathway illustrates the transformation of a natural compound into a synthetic derivative via a series of chemical reactions. It emphasizes synthetic organic chemistry techniques applied to medicinal chemistry.
Transcribed Image Text:This is a reaction pathway depicting the synthesis of Lysergic acid diethylamide (LSD) from Ergotamine. 1. **Ergotamine Structure:** - The chemical structure on the far left is Ergotamine, a complex molecule containing a bicyclic hexahydroindole ring system fused with a lysergic acid moiety. 2. **Transformation A:** - The first arrow labeled "A" indicates the initial transformation where Ergotamine undergoes a reaction to form an intermediary compound. This involves modifying the side chain while retaining the indole and hexahydroindole ring systems. 3. **Transformation B:** - The second arrow labeled "B" represents the conversion of the intermediate compound to another structure, showing the replacement of a hydroxyl group with a chlorine atom, and the retention of the core bicyclic structure. 4. **Transformation C:** - The final step, labeled "C", involves the transformation to Lysergic acid diethylamide (LSD), characterized by the addition of a diethylamide group. 5. **Lysergic Acid Diethylamide (LSD) Structure:** - The final structure on the far right is LSD, featuring a core lysergic acid structure with a diethylamide functional group. This pathway illustrates the transformation of a natural compound into a synthetic derivative via a series of chemical reactions. It emphasizes synthetic organic chemistry techniques applied to medicinal chemistry.
**Question 35**

Ergotamine, an alkaloid isolated from a fungus that infects rye, is used medicinally for the treatment of acute migraine attacks (sometimes in combination with caffeine). It is a controlled substance in the United States as it is a commonly used precursor for the production of lysergic acid diethylamide (LSD).

Look at the synthetic pathway below. 

[Note: There is no diagram or graph present in the image above.]
Transcribed Image Text:**Question 35** Ergotamine, an alkaloid isolated from a fungus that infects rye, is used medicinally for the treatment of acute migraine attacks (sometimes in combination with caffeine). It is a controlled substance in the United States as it is a commonly used precursor for the production of lysergic acid diethylamide (LSD). Look at the synthetic pathway below. [Note: There is no diagram or graph present in the image above.]
Expert Solution
steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Lipids
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
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY