The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans

Matthew D. Metcalf; Mario D. Aceto; Louis S. Harris; James H. Woods; John R. Traynor; Andrew Coop; Everette L. May

doi:10.1016/j.bmc.2007.10.030

The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans

Matthew D. Metcalf, Mario D. Aceto, Louis S. Harris, James H. Woods, John R. Traynor, Andrew Coop, Everette L. May

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	869-873
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	2
DOIs	https://doi.org/10.1016/j.bmc.2007.10.030
State	Published - Jan 15 2008
Externally published	Yes

Keywords

Benzomorphan
N-Normetazocine
Normetazocine
Opioid

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2007.10.030

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title = "The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans",

abstract = "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.",

keywords = "Benzomorphan, N-Normetazocine, Normetazocine, Opioid",

author = "Metcalf, {Matthew D.} and Aceto, {Mario D.} and Harris, {Louis S.} and Woods, {James H.} and Traynor, {John R.} and Andrew Coop and May, {Everette L.}",

note = "Funding Information: The authors thank the College on Problems of Drug Dependence, the Drug Evaluation Committee, NIDA Grants DA-13583 and DA-00254. M.D.M. is the recipient of a Ruth L. Kirschstein NRSA fellowship DA-18025, and A.C. is the recipient of an Independent Scientist Award, DA-19634. ",

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AU - Metcalf, Matthew D.

AU - Aceto, Mario D.

AU - Harris, Louis S.

AU - Woods, James H.

AU - Traynor, John R.

AU - Coop, Andrew

AU - May, Everette L.

N1 - Funding Information: The authors thank the College on Problems of Drug Dependence, the Drug Evaluation Committee, NIDA Grants DA-13583 and DA-00254. M.D.M. is the recipient of a Ruth L. Kirschstein NRSA fellowship DA-18025, and A.C. is the recipient of an Independent Scientist Award, DA-19634.

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Y1 - 2008/1/15

N2 - 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.

AB - 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.

KW - Benzomorphan

KW - N-Normetazocine

KW - Normetazocine

KW - Opioid

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The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans

Abstract

Keywords

ASJC Scopus subject areas

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