This document discusses drugs that affect the central nervous system, specifically morphine alkaloids. It provides information on morphine, codeine, thebaine, apomorphine, oxycodone, and oxymorphone, including their molecular formulas and brief histories. It also discusses the chemistry, structure-activity relationships, mechanisms of action, and uses of morphine alkaloids. The presentation was given by Aswini Sasidharan of the Department of Pharmaceutical Chemistry at Grace College of Pharmacy in Palakkad.

1. Drugs Affecting
the Central Nervous System
Presented by,
ASWINI SASIDHARAN
DEPT. OF PHARMACEUTICAL CHEMISTRY
GRACE COLLEGE OF PHARMACY, PALAKKAD

2. Morphine Alkaloids
•Drugs acting on the CNS.
•Natural opium alkaloids.
•Dried extract obtained from the capsule of poppy plant
known as papaverum somniferum.

3. Morphine Alkaloids
1. Morphine
2. Codeine
3. Thebaine
4. Apomorphine
5. Oxycodone
6. Oxymorphone

4. Morphine
Molecular Formula: C H NO
19
17 3

5. Oxymorphone
Molecular Formula: C H NO
19
17 4

6. History
•Morphine was isolated from opium.
•By the German Chemist F W A Serturner in 1804.
•It has the power to reduce the level of physical
distress.

7. Codeine
Molecular Formula: C H NO
18 21 3

8. Oxycodone
Molecular Formula: C H NO
18 21 4

9. History
•First isolated by French chemist Pierre-Jean Robiquet
in 1832.
•Codein is extracted directly from opium, but mostly
from morphine & another opium derivatives.

10. Thebaine
Molecular Formula: C H NO
19 21 3

11. History
•Thebaine (paramorphine), also known as Codeine
methyl enol ether.
•It is an opiate alkaloid.
•Name comes from the Greek word “Theber” an ancient
city in Upper Egypt.

12. Apomorphine
Molecular Formula: C H NO
17 17 2

13. History
•The use of apomorphine was suggested by Weil in
France in 1884, although seemingly not pursued until
1951.
•Clinical use was reported in 1970.

14. CHEMISTRY
A
B
C
D
E
•5 Membered ring structure.
•Ring A - Aromatic ring.
•Ring B - Cyclohexane ring.
•Ring C - Cyclohexene ring.
•Ring D - Pyridine ring.
•Ring E- Tetrahydro Furan Ring.
•3 Rings (A,B, & C) lies in the same plane.
•2 Rings (D & E) are perpenticular to the
plane.
•Tertiary Nitrogen, Alcoholic & Phenolic
hydroxyl group, Ether bridge.

15. SAR
•The presence of OH group at C-3 position
will enhances the activity.
Eg; Morphine.
•The removal of ether bridge from the
compound increases the potency.
•The modification in the OH group at C-6
position yields ester or ether, that increases
the activity of the compound.
Eg; Thebaine.
Ether bridge

16. •Oxidation & Reduction at 7th & 8th
position (C=C), increases the activity of
the compound.
•Masking the phenol group will decreases
the activity.
•Modification in N-CH3 to N-CH at C-9,
decreases the activty.
•Modification in N-CH3 to CH2-CH2-
C6H5, increases the activity.
•Removal of double bond (C7-C8),
enhances the potency of the drug.
MORPHINE

17. Mechanism Of Action

18. Uses
•Relieve moderate to severe pain (Analgesics).
•Relieve stuffy nose (Decongestants).
•Used for the pain relief in: Myocardial Infarction.
Long bone fracture.
Postoperative Patients.
Terminal stages of cancer.
Pulmonary embolism.

19. REFERENCES
1. Natural products chemistry- sources, separation & structure by Raymond Cooper &
George Nicola, Pageno; 91-95.
2.Textbook of medicinal chemistry, volume I by V Alagarsamy, Pageno; 247-252.
3.Wilson and Gisvolds Textbook of organic Medicinal Pharmaceutical chemistry, 12 th
Edition by John M Beale & John H Block, Pageno; 783-785.
4. Essential’s of pharmacology, 7th Edition by K D Thripathi.

20. THANK YOU