Literature DB >> 8240925

Synthesis and evaluation of the antidepressant activity of the enantiomers of bupropion.

D L Musso1, N B Mehta, F E Soroko, R M Ferris, E B Hollingsworth, B T Kenney.   

Abstract

The synthesis of the enantiomers of bupropion, (rac)-2-tert-butylamino-3'-chloropropiophenone 1 (Wellbutrin) is described. The enantiomers were compared with the racemate in both the tetrabenazine-induced sedation model and the inhibition of uptake of biogenic amine assay. No significant differences were found in their potencies to reverse tetrabenazine-induced sedation in mice or in their IC50 values as inhibitors of biogenic amine uptake into nerve endings obtained from mouse brain.

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Year:  1993        PMID： 8240925     DOI： 10.1002/chir.530050704

Source DB:  PubMed          Journal:  Chirality        ISSN： 0899-0042            Impact factor:   2.437


  9 in total

Review 1.  Review of the pharmacology and clinical profile of bupropion, an antidepressant and tobacco use cessation agent.

Authors:  Linda P Dwoskin; Anthony S Rauhut; Kelley A King-Pospisil; Michael T Bardo
Journal:  CNS Drug Rev       Date:  2006 Fall-Winter

2.  Development and validation of a high-throughput stereoselective LC-MS/MS assay for bupropion, hydroxybupropion, erythrohydrobupropion, and threohydrobupropion in human plasma.

Authors:  Aaron M Teitelbaum; Alicia M Flaker; Evan D Kharasch
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2016-02-27       Impact factor: 3.205

3.  Conformational preferences of the potent dopamine reuptake blocker BTCP and its analogs and their incorporation into a pharmacophore model.

Authors:  M Froimowitz; K M Wu; J Rodrigo; C George
Journal:  J Comput Aided Mol Des       Date:  2000-02       Impact factor: 3.686

4.  Amphetamine enantiomers inhibit homomeric α7 nicotinic receptor through a competitive mechanism and within the intoxication levels in humans.

Authors:  Daniel R Garton; Sharmaine G Ross; Rafael Maldonado-Hernández; Matthias Quick; José A Lasalde-Dominicci; José E Lizardi-Ortiz
Journal:  Neuropharmacology       Date:  2018-10-23       Impact factor: 5.250

5.  1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors.

Authors:  Peter C Meltzer; David Butler; Jeffrey R Deschamps; Bertha K Madras
Journal:  J Med Chem       Date:  2006-02-23       Impact factor: 7.446

6.  Stereoselective Effects of Abused "Bath Salt" Constituent 3,4-Methylenedioxypyrovalerone in Mice: Drug Discrimination, Locomotor Activity, and Thermoregulation.

Authors:  Brenda M Gannon; Adrian Williamson; Masaki Suzuki; Kenner C Rice; William E Fantegrossi
Journal:  J Pharmacol Exp Ther       Date:  2016-01-14       Impact factor: 4.030

7.  Development, validation and application of a comprehensive stereoselective LC/MS-MS assay for bupropion and oxidative, reductive, and glucuronide metabolites in human urine.

Authors:  Aaron M Teitelbaum; Alicia M Flaker; Evan D Kharasch
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2016-05-24       Impact factor: 3.205

8.  Probing the Release of Bupropion and Naltrexone Hydrochloride Salts from Biopolymeric Matrices of Diverse Chemical Structures.

Authors:  Angeliki Siamidi; Aikaterini Dedeloudi; Marilena Vlachou
Journal:  Polymers (Basel)       Date:  2021-04-30       Impact factor: 4.329

9.  Population model analysis of chiral inversion and degradation of bupropion enantiomers, and application to enantiomer specific fraction unbound determination in rat plasma and brain.

Authors:  Chandrali Bhattacharya; Andrea R Masters; Christine Bach; Robert E Stratford
Journal:  J Pharm Biomed Anal       Date:  2020-12-26       Impact factor: 3.935
  9 in total

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