The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans.
To investigate the effects of carboxylic ester and acid moieties as the N-substituent of opioids, a short series of racemic N-substituted normetazocines was prepared. The introduction of both groups as the normetazocine N-substituent produced compounds which displayed low potency in vitro and in vivo, with the esters displaying the greater activity. The pharmacology of the compounds is discussed with implications resulting from potential in vivo metabolic hydrolysis.
Metcalf
Matthew D
MD
Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Room 637, Baltimore, MD 21201, USA.
Aceto
Mario D
MD
Harris
Louis S
LS
Woods
James H
JH
Traynor
John R
JR
Coop
Andrew
A
May
Everette L
EL
D000701:Analgesics, Opioid / Q000737:chemistry* / Q000494:pharmacology*; D001575:Benzomorphans / Q000737:chemistry / Q000494:pharmacology; D002264:Carboxylic Acids / Q000737:chemistry / Q000494:pharmacology; D004952:Esters; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000701:Analgesics, Opioid; D001575:Benzomorphans; D002264:Carboxylic Acids; D004952:Esters