Novel aminopropiophenones as potential antidepressants

@article{Foley2003NovelAA,
  title={Novel aminopropiophenones as potential antidepressants},
  author={Kevin F. Foley and Nicholas V Cozzi},
  journal={Drug Development Research},
  year={2003},
  volume={60}
}
  • K. Foley, N. Cozzi
  • Published 1 December 2003
  • Psychology, Biology
  • Drug Development Research
The atypical antidepressant drug bupropion and the psychostimulant drug methcathinone are both members of a chemical class known as aminopropiophenones. Differences in the psychoactive effects of these two drugs result from small variations in their chemical structures, but the relationship between chemical structure and psychoactivity has not been characterized. To investigate how structural modifications to aminopropiophenones affect antidepressant or stimulant activity, we synthesized… 
View on Wiley
bitnest.netfirms.com
55 Citations
Highly Influential Citations
1
Background Citations
10
Methods Citations
1
Results Citations
3

55 Citations

Pharmacological examination of trifluoromethyl ring-substituted methcathinone analogs.
Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention.
  • R. Glennon
  • Chemistry, Biology
    Advances in pharmacology
  • 2014
Bupropion and bupropion analogs as treatments for CNS disorders.
The naphyrone story: The alpha or beta-naphthyl isomer?
TLDR
This provides the first report of α-naphyrone in the scientific literature and the ability to differentiate it from the β-isomer should be of interest to forensic and clinical communities.
Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for cocaine addiction.
TLDR
2-(N-Cyclopropylamino)-3-chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction.
Systematic Structure-Activity Studies on Selected 2-, 3-, and 4-Monosubstituted Synthetic Methcathinone Analogs as Monoamine Transporter Releasing Agents.
TLDR
The releasing ability of several simple methcathinone analogs at the three monoamine transporters at the DAT, NET, and SERT was examined, suggesting relatively similar structure-activity relationships (at least for the compounds examined here).
Structure-Activity Relationships of Synthetic Cathinones.
TLDR
An SAR picture is beginning to emerge, and key structural features, such as the nature of the terminal amine, the size of the α-substituent, stereochemistry, and the presence and position of aromatic substituents, are being found to impact action and transporter selectivity.
Analytical characterization of three trifluoromethyl-substituted methcathinone isomers.
TLDR
Three trifluoromethyl analogues of the psychostimulant methcathinone, with a CF(3) substituent at the 2-, 3- and 4-position of the phenyl ring, have been prepared for analytical characterization and show central nervous system effects.
Pharmacokinetic and pharmacodynamic of bupropion: integrative overview of relevant clinical and forensic aspects
TLDR
The characterization of the polymorphic enzymes involved in the metabolism of bupropion is essential to understand factors that may influence the interindividual and intraindividual variability in bupropions metabolite exposure, including the evaluation of potential drug–drug interactions and pharmacogenetic implications.
Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for smoking cessation.
Bupropion (2a) analogues were synthesized and tested for their ability to inhibit monoamine uptake and to antagonize the effects of human alpha3beta4*, alpha4beta2, alpha4beta4, and alpha1* nAChRs.…
...
...

References

SHOWING 1-10 OF 57 REFERENCES
Cathinone: An Investigation of Several N-Alkyl and Methylenedioxy-Substituted Analogs
The effect of N‐alkyl chain length and stereochemistry on the absorption, metabolism and urinary excretion of N‐alkylamphetamines in man *
Urinary excretion in man, of the unchanged drug and metabolite amphetamine, has been investigated after the (+)‐ and (‐)‐isomers of methyl‐, ethyl‐, n‐propyl‐ and n‐butyl‐ amphetamine had been taken…
Methcathinone: A new and potent amphetamine-like agent
Effects of amphetamine and its hydroxylated metabolites on central noradrenergic mechanisms.
TLDR
The results of the present study emphasize the importance of metabolic considerations in the interpretation of the action of A after its systemic or intraventricular administration.
The contribution of the metabolite p-hydroxyamphetamine to the central actions of p-methoxyamphetamine
TLDR
Data indicate that although PHA is more effective than PMA at altering 5HT and dopamine kinetics in vivo, it is unlikely to achieve sufficient brain concentrations to contribute to the central effects of PMA.
Ephedrone: 2-Methylamino-1-Phenylpropan-1-One (Jeff)
Ephedrine and pseudoephedrine, commonly used in clandestine laboratories within the United States to synthesize methamphetamine by means of reduction, are utilized within the Union of Soviet…
Bupropion: clinical assay for amphetamine-like abuse potential.
TLDR
It is concluded that, despite bupropion's reinforcing properties in animals, the compound is not amphetamine-like and is unlikely to give rise to such abuse in humans.
Evidence that the Acute Behavioral and Electrophysiological Effects of Bupropion (Wellbutrin®) Are Mediated by a Noradrenergic Mechanism
TLDR
The results suggest that bupropion preferentially affects NE neurons in locus coeruleus at doses that are active in animal antidepressant tests, and require a reserpine-sensitive store of NE and occur at doses having activity in antidepressant screening tests.
Anorectic and behavioural effects of bupropion.
Cocaine-stimulus generalization to two new designer drugs: Methcathinone and 4-methylaminorex
...
...