Literature DB >> 24393077

Preliminary pharmacological evaluation of enantiomeric morphinans.

Anna W Sromek1, Brian A Provencher, Shayla Russell, Elena Chartoff, Brian I Knapp, Jean M Bidlack, John L Neumeyer.   

Abstract

A series of levo- and dextromorphinan pairs have been synthesized and evaluated for their affinities to the mu, kappa, and delta opioid receptors, the N-methyl-D-aspartate (NMDA) channel, and sigma 1 and 2 receptors. It was found that levo isomers tended to have higher affinities at the opioid receptors and moderate to high affinities to the NMDA and sigma receptors, while dextro isomers tended to have lower affinities to the opioid receptors but comparatively higher affinities to the NMDA and sigma receptors. This series of compounds have interesting and complex pharmacological profiles, and merit further investigation as potential therapies for drug abuse treatment.

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Year:  2014        PMID: 24393077      PMCID: PMC3930996          DOI: 10.1021/cn400205z

Source DB:  PubMed          Journal:  ACS Chem Neurosci        ISSN: 1948-7193            Impact factor:   4.418


  28 in total

1.  Comparative effects of dextromethorphan and dextrorphan on morphine, methamphetamine, and nicotine self-administration in rats.

Authors:  S D Glick; I M Maisonneuve; H A Dickinson; B A Kitchen
Journal:  Eur J Pharmacol       Date:  2001-06-22       Impact factor: 4.432

2.  Anticonvulsant effects of new morphinan derivatives.

Authors:  H C Kim; T Nabeshima; W K Jhoo; K H Ko; W K Kim; E J Shin; M Cho; P H Lee
Journal:  Bioorg Med Chem Lett       Date:  2001-07-09       Impact factor: 2.823

3.  Kappa-Opioid and NMDA glutamate receptors are differentially targeted within rat medial prefrontal cortex.

Authors:  Adena L Svingos; Eric E O Colago
Journal:  Brain Res       Date:  2002-08-16       Impact factor: 3.252

4.  Effects of mixed-action kappa/mu opioids on cocaine self-administration and cocaine discrimination by rhesus monkeys.

Authors:  Carrie A Bowen; S Stevens Negus; Rushi Zong; John L Neumeyer; Jean M Bidlack; Nancy K Mello
Journal:  Neuropsychopharmacology       Date:  2003-03-05       Impact factor: 7.853

5.  Studies in the (+)-morphinan series. 5. Synthesis and biological properties of (+)-naloxone.

Authors:  I Iijima; J Minamikawa; A E Jacobson; A Brossi; K C Rice
Journal:  J Med Chem       Date:  1978-04       Impact factor: 7.446

6.  Attenuation of the stimulant and convulsant effects of cocaine by 17-substituted-3-hydroxy and 3-alkoxy derivatives of dextromethorphan.

Authors:  Agustin Zapata; Maciej Gasior; Beth Geter-Douglass; Frank C Tortella; Amy Hauck Newman; Jeffrey M Witkin
Journal:  Pharmacol Biochem Behav       Date:  2003-01       Impact factor: 3.533

7.  Opioid activation of toll-like receptor 4 contributes to drug reinforcement.

Authors:  M R Hutchinson; A L Northcutt; T Hiranita; X Wang; S S Lewis; J Thomas; K van Steeg; T A Kopajtic; L C Loram; C Sfregola; E Galer; N E Miles; S T Bland; J Amat; R R Rozeske; T Maslanik; T R Chapman; K A Strand; M Fleshner; R K Bachtell; A A Somogyi; H Yin; J L Katz; K C Rice; S F Maier; L R Watkins
Journal:  J Neurosci       Date:  2012-08-15       Impact factor: 6.167

8.  Kappa opioid agonists as targets for pharmacotherapies in cocaine abuse.

Authors:  J L Neumeyer; N K Mello; S S Negus; J M Bidlack
Journal:  Pharm Acta Helv       Date:  2000-03

9.  d-morphine, but not l-morphine, has low micromolar affinity for the non-competitive N-methyl-D-aspartate site in rat forebrain. Possible clinical implications for the management of neuropathic pain.

Authors:  M Stringer; M K Makin; J Miles; J S Morley
Journal:  Neurosci Lett       Date:  2000-12-01       Impact factor: 3.046

10.  Synthesis and pharmacological evaluation of aminothiazolomorphinans at the mu and kappa opioid receptors.

Authors:  Brian A Provencher; Anna W Sromek; Wei Li; Shayla Russell; Elena Chartoff; Brian I Knapp; Jean M Bidlack; John L Neumeyer
Journal:  J Med Chem       Date:  2013-10-29       Impact factor: 7.446

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  4 in total

1.  A Cyclic Tetrapeptide ("Cyclodal") and Its Mirror-Image Isomer Are Both High-Affinity μ Opioid Receptor Antagonists.

Authors:  Grazyna Weltrowska; Thi M-D Nguyen; Nga N Chung; JodiAnne Wood; Xiaoyu Ma; Jason Guo; Brian C Wilkes; Yang Ge; André Laferrière; Terence J Coderre; Peter W Schiller
Journal:  J Med Chem       Date:  2016-10-03       Impact factor: 7.446

Review 2.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

3.  Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.

Authors:  Bryan T Ingoglia; Corin C Wagen; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2019-05-11       Impact factor: 2.457

4.  In silico design of novel probes for the atypical opioid receptor MRGPRX2.

Authors:  Katherine Lansu; Joel Karpiak; Jing Liu; Xi-Ping Huang; John D McCorvy; Wesley K Kroeze; Tao Che; Hiroshi Nagase; Frank I Carroll; Jian Jin; Brian K Shoichet; Bryan L Roth
Journal:  Nat Chem Biol       Date:  2017-03-13       Impact factor: 15.040

  4 in total

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