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

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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 - May, Everette L.

AU - Jacobson, Arthur E.

AU - Mattson, Mariena V.

AU - Coop, Andrew

AU - Aceto, Mario D.

AU - Bowman, Edward R.

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AU - Woods, James H.

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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