In

Class/tutorial Activity

Consider the ‘Deconstructing’ of Morphine

H3C H3C

N Removal of N
Removal of N

(ring-C and E)

(ring- E) H

HO O

OH HO HO

Removal of
µ -opioid agonist
(ring-B, C k-opioid agonist
µ -opioid agonist µ-opioid antagonist

and E)

N N
N Removal of
µ -opioid agonist
rings B, C,

O D and E
µ -opioid agonist

H O µ -opioid agonist Structure

N modified of 4- O

phenylpiperidine O

( plus anilido
group)

39


• Morphine Structure Highly analgesics -Tolerance -dependence.

• morphinans are more potent and longer acting than morphine.

• Benzomorphans are clinically useful compounds with reasonable analgesic activity,

activity less addictive and tolerance.

• The first of these agents is pethidine (meperdine) :Rapid onset -short dution of action
(ethyl ester)?? -µ agoinst with 25% the activity of morphine - analgesic activity. - does
not inhibit cough - euphoria.

• fentanyl: which is 100 times more active than - no ester group (longer duration of
action than pethidine) - very lipophilic (it has got an ethyl phenyl group).

• oraly active diphenylheptanone Morphine (Methadone) : has less side effects