1.
J Med Chem
; 27(8): 1090-2, 1984 Aug.
Article
in English
| MEDLINE
| ID: mdl-6086925
ABSTRACT
8 beta-[Bis(2-chloroethyl)amino]-6,7-didehydro-3-hydroxy-17-methyl-4 ,5 alpha-epoxymorphinan (3) was synthesized from codeine, and its configuration at C-8 was determined by NMR. When evaluated in the guinea pig ileum and mouse vas deferens preparations, 3 was found to be a feeble, reversible agonist in both tissues without any irreversible agonist or antagonist activity. The fact that the 8 beta-bis-(2-hydroxyethyl)amino analogue was devoid of opioid activity suggests that steric hindrance to ligand-receptor association by a bulky 8-substituent may be responsible for this inactivity.
Subject(s)
Morphinans/chemical synthesis , Receptors, Opioid/metabolism , Animals , Guinea Pigs , Ileum/metabolism , Magnetic Resonance Spectroscopy , Male , Mice , Morphinans/metabolism , Vas Deferens/metabolism
2.
J Med Chem
; 17(1): 124-9, 1974 Jan.
Article
in English
| MEDLINE
| ID: mdl-4808459
Subject(s)
Methadone , Chemical Phenomena , Chemistry , Circular Dichroism , Deuterium , Isomerism , Magnetic Resonance Spectroscopy , Molecular Conformation , Stereoisomerism
3.
J Med Chem
; 17(1): 129-31, 1974 Jan.
Article
in English
| MEDLINE
| ID: mdl-4808460
Subject(s)
Analgesics/chemical synthesis , Piperidines/chemical synthesis , Analgesics/pharmacology , Animals , Magnetic Resonance Spectroscopy , Mice , Molecular Conformation , Optical Rotation , Piperidines/pharmacology , Propionates/chemical synthesis , Propionates/pharmacology , Reaction Time/drug effects , Stereoisomerism , Structure-Activity Relationship
4.
J Med Chem
; 16(6): 589-91, 1973 Jun.
Article
in English
| MEDLINE
| ID: mdl-4714984
5.
J Med Chem
; 16(3): 203-5, 1973 Mar.
Article
in English
| MEDLINE
| ID: mdl-4733100