Synthesis, in vitro, and in vivo activity of N-p-substituted-benzyl- (- )- and (+)-N-normetazocines, (-)- and (+)-N-normorphinans, N- norketobemidones, and (-)-N-nor-4,5-epoxymorphinans

Everette L. May; Arthur E. Jacobson; Mariena V. Mattson; Andrew Coop; Mario D. Aceto; Edward R. Bowman; John R. Traynor; James H. Woods; Louis S. Harris

Synthesis, in vitro, and in vivo activity of N-p-substituted-benzyl- (- )- and (+)-N-normetazocines, (-)- and (+)-N-normorphinans, N- norketobemidones, and (-)-N-nor-4,5-epoxymorphinans

Everette L. May, Arthur E. Jacobson, Mariena V. Mattson, Andrew Coop, Mario D. Aceto, Edward R. Bowman, John R. Traynor, James H. Woods, Louis S. Harris

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

13 Scopus citations

Abstract

N-benzyl- and N-p-nitrobenzyl-N-norketobemidone, and N-p-fluorobenzyl- N-normetazocine have been synthesized and found to have equivalent or higher affinity for the (σ(i)-binding site than the previously described (+)-N- benzylnormetazocine. None of the examined compounds had significant affinity for the σ₂-binding site and few had high affinity for μ-, δ-, and κ- opioid receptors. (-)-N-Benzyl-N-normetazocine displayed weak agonist- antagonist activity and (-)-N-benzylnoroxymorphone had one-tenth the antagonist activity of naloxone.

Original language	English (US)
Pages (from-to)	311-321
Number of pages	11
Journal	Medicinal Chemistry Research
Volume	8
Issue number	6
State	Published - 1998
Externally published	Yes

ASJC Scopus subject areas

Pharmacology, Toxicology and Pharmaceutics(all)
Organic Chemistry

Cite this

May, E. L., Jacobson, A. E., Mattson, M. V., Coop, A., Aceto, M. D., Bowman, E. R., Traynor, J. R., Woods, J. H., & Harris, L. S. (1998). Synthesis, in vitro, and in vivo activity of N-p-substituted-benzyl- (- )- and (+)-N-normetazocines, (-)- and (+)-N-normorphinans, N- norketobemidones, and (-)-N-nor-4,5-epoxymorphinans. Medicinal Chemistry Research, 8(6), 311-321.

Synthesis, in vitro, and in vivo activity of N-p-substituted-benzyl- (- )- and (+)-N-normetazocines, (-)- and (+)-N-normorphinans, N- norketobemidones, and (-)-N-nor-4,5-epoxymorphinans. / May, Everette L.; Jacobson, Arthur E.; Mattson, Mariena V.; Coop, Andrew; Aceto, Mario D.; Bowman, Edward R.; Traynor, John R.; Woods, James H.; Harris, Louis S.

In: Medicinal Chemistry Research, Vol. 8, No. 6, 1998, p. 311-321.

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

May, Everette L. ; Jacobson, Arthur E. ; Mattson, Mariena V. ; Coop, Andrew ; Aceto, Mario D. ; Bowman, Edward R. ; Traynor, John R. ; Woods, James H. ; Harris, Louis S. / Synthesis, in vitro, and in vivo activity of N-p-substituted-benzyl- (- )- and (+)-N-normetazocines, (-)- and (+)-N-normorphinans, N- norketobemidones, and (-)-N-nor-4,5-epoxymorphinans. In: Medicinal Chemistry Research. 1998 ; Vol. 8, No. 6. pp. 311-321.

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title = "Synthesis, in vitro, and in vivo activity of N-p-substituted-benzyl- (- )- and (+)-N-normetazocines, (-)- and (+)-N-normorphinans, N- norketobemidones, and (-)-N-nor-4,5-epoxymorphinans",

abstract = "N-benzyl- and N-p-nitrobenzyl-N-norketobemidone, and N-p-fluorobenzyl- N-normetazocine have been synthesized and found to have equivalent or higher affinity for the (σ(i)-binding site than the previously described (+)-N- benzylnormetazocine. None of the examined compounds had significant affinity for the σ2-binding site and few had high affinity for μ-, δ-, and κ- opioid receptors. (-)-N-Benzyl-N-normetazocine displayed weak agonist- antagonist activity and (-)-N-benzylnoroxymorphone had one-tenth the antagonist activity of naloxone.",

author = "May, {Everette L.} and Jacobson, {Arthur E.} and Mattson, {Mariena V.} and Andrew Coop and Aceto, {Mario D.} and Bowman, {Edward R.} and Traynor, {John R.} and Woods, {James H.} and Harris, {Louis S.}",

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AU - Jacobson, Arthur E.

AU - Mattson, Mariena V.

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AU - Harris, Louis S.

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AB - N-benzyl- and N-p-nitrobenzyl-N-norketobemidone, and N-p-fluorobenzyl- N-normetazocine have been synthesized and found to have equivalent or higher affinity for the (σ(i)-binding site than the previously described (+)-N- benzylnormetazocine. None of the examined compounds had significant affinity for the σ2-binding site and few had high affinity for μ-, δ-, and κ- opioid receptors. (-)-N-Benzyl-N-normetazocine displayed weak agonist- antagonist activity and (-)-N-benzylnoroxymorphone had one-tenth the antagonist activity of naloxone.

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Synthesis, in vitro, and in vivo activity of N-p-substituted-benzyl- (- )- and (+)-N-normetazocines, (-)- and (+)-N-normorphinans, N- norketobemidones, and (-)-N-nor-4,5-epoxymorphinans

Abstract

ASJC Scopus subject areas

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