192374-15-5

Usage

Uses

Used in Pharmaceutical Industry:
(R,R)-Hydroxy Bupropion is used as an active pharmaceutical ingredient (API) for its antidepressant properties. As a metabolite of Bupropion, it contributes to the overall therapeutic effects of the parent drug, potentially enhancing the treatment of depression and related mood disorders.
Used in Research and Development:
In the field of scientific research, (R,R)-Hydroxy Bupropion serves as a crucial compound for studying the mechanisms of action, metabolism, and potential side effects of Bupropion. This helps in understanding the drug's behavior in the human body and aids in the development of more effective and safer antidepressant medications.
Used in Drug Metabolism Studies:
(R,R)-Hydroxy Bupropion is utilized as a reference compound in drug metabolism studies. These studies are essential for understanding how drugs are processed and eliminated from the body, which can lead to the optimization of drug dosages and the development of personalized treatment plans for patients.
Used in Quality Control and Standardization:
The (R,R)-Hydroxy Bupropion is also used as a reference standard in the quality control and standardization of Bupropion-containing pharmaceutical products. This ensures that the active ingredient's purity, potency, and consistency meet the required standards, ultimately contributing to the safety and efficacy of the medication.

InChI:InChI=1/C13H18ClNO2/c1-9-13(16,17-8-12(2,3)15-9)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3/t9-,13+/m1/s1

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Relevant academic research and scientific papers

HYDROXYBUPROPION ANALOGUES FOR TREATING DRUG DEPENDENCE

The invention provides hydroxybupropion analogues capable of inhibiting the reuptake of one or more monoamines and/or acting as antagonists at nicotinic acetylcholine receptors. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin and/or may selectively bind to one or more nicotinic acetylcholine receptor subtypes. Such compounds may be used to treat conditions that are responsive to modification of monoamine levels and/or antagonism of nicotinic acetylcholine receptors, including drug dependency, depression, and obesity.

Synthesis and characterization of in vitro and in vivo profiles of hydroxybupropion analogues: Aids to smoking cessation

To create potentially superior aids to smoking cessation and/or antidepressants and to elucidate bupropions possible mechanisms of action(s), 23 analogues based on its active hydroxymetabolite (2S,3S)-4a were synthesized and tested for their abilities to inhibit monoamine uptake and nAChR subtype activities in vitro and acute effects of nicotine in vivo. The 3′,4′-dichlorophenyl [(±)-4n], naphthyl (4r), and 3-chlorophenyl or 3-propyl analogues 4s and 4t, respectively, had higher inhibitory potency and/or absolute selectivity than (2S,3S)-4a for inhibition of DA, NE, or 5HT uptake. The 3′-fluorophenyl, 3′-bromophenyl, and 4-biphenyl analogues 4c, 4d, and 4l, respectively, had higher potency for antagonism of α4β2-nAChR than (2S,3S)-4a. Several analogues also had higher potency than (2S,3S)-4a as antagonists of nicotine-mediated antinociception in the tail-flick assay. The results suggest that compounds acting via some combination of DA, NE, or 5HT inhibition and/or antagonism of α4β2-nAChR can potentially be new pharmacotherapeutics for treatment of nicotine dependence.

Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate

A stereospecific method for the synthesis of enantiopure α-aminoketone from its corresponding α-hydroxy-ketone via the triflate intermediate is discussed. This strategy provides a rapid and efficient route for the preparation of either enantiomer of bupro