Opium Analgesics

1
Opium Analgesics

• Chapter 21

2
Opiates

• Analgesic properties
• Problem?
• Why opiates?
• What are opiates?

3
Poppy

• Papaver somniferum
• Sleep-bringing poppy
• Many varieties, colors
• Poppy seed
• Latex from pod
• Tincture
• Smoked

4
Opium

• Oldest drug
• History
• Mixture of alkaloids
• Morphine

5
Morphine

• Timeline
• 1803 isolated
• 1833 purified
• 1853 medicine
• 1881 functional groups identified
• 1925 structure proposed
• 1953 synthesis
• 1968 structure confirmed
• Properties
• Structure
• Stereochemistry

6
Structure-activityrelationships

• Phenolic OH
• Other alcohol
• Double bond
• N-methyl group
• Aromatic ring
• Ether bridge

7
Development of morphine analogs

• Remember this pharmacophore example?

8
Development of morphine analogs

• Vary substituents

9
Development of morphine analogs

• Vary substituents
• Extension of drug

10
Development of morphine analogs

• Vary substituents
• Extension of drug
• Simplification of structure

11
Development of morphine analogs

• Vary substituents
• Extension of drug
• Simplification of structure
• Rigidification

12
Receptor theory

• m receptor
• k receptor
• d receptor

13
A question.