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Hydroxy Bupropion (CAS 357399-43-0)

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Alternate Names:
2-Hydroxy-2-(3′-chlorophenyl)-3,5,5-trimethylmorpholine
Application:
Hydroxy Bupropion is a bupropion metabolite
CAS Number:
357399-43-0
Purity:
≥98%
Molecular Weight:
255.74
Molecular Formula:
C13H18ClNO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Hydroxy Bupropion is a major metabolite of the dopamine transport inhibitor and nicotinic antagonist bupropion (sc-201121). It is formed by hydroxylation of bupropion on the tert-butyl group and cyclizes to an acetal. Hydroxy Bupropion acts as a monoamine reuptake inhibitor (MRI). It It has been found to increase the levels of dopamine, serotonin, and norepinephrine in the brain, as well as decrease the levels of cortisol. This product is a racemic preparation of the R,R-hydroxy bupropion (sc-212634) and S,S-hydroxy bupropion (sc-212825) isomers.


Hydroxy Bupropion (CAS 357399-43-0) References

  1. Metabolism of some 'second'- and 'fourth'-generation antidepressants: iprindole, viloxazine, bupropion, mianserin, maprotiline, trazodone, nefazodone, and venlafaxine.  |  Rotzinger, S., et al. 1999. Cell Mol Neurobiol. 19: 427-42. PMID: 10379419
  2. Bupropion is a nicotinic antagonist.  |  Slemmer, JE., et al. 2000. J Pharmacol Exp Ther. 295: 321-7. PMID: 10991997
  3. Role of polymorphic human CYP2B6 in cyclophosphamide bioactivation.  |  Xie, HJ., et al. 2003. Pharmacogenomics J. 3: 53-61. PMID: 12629583
  4. Stereoselective analysis of hydroxybupropion and application to drug interaction studies.  |  Xu, H., et al. 2007. Chirality. 19: 163-70. PMID: 17167747
  5. Drug interaction study between bupropion and ticlopidine in male CF-1 mice.  |  Molnari, JC., et al. 2011. Biol Pharm Bull. 34: 447-51. PMID: 21372402
  6. Quantification of 4 antidepressants and a metabolite by LC-MS for therapeutic drug monitoring.  |  Choong, E., et al. 2011. J Chromatogr B Analyt Technol Biomed Life Sci. 879: 1544-50. PMID: 21524943
  7. Analysis of 100 pharmaceuticals and their degradates in water samples by liquid chromatography/quadrupole time-of-flight mass spectrometry.  |  Ferrer, I. and Thurman, EM. 2012. J Chromatogr A. 1259: 148-57. PMID: 22487190
  8. Widespread occurrence of neuro-active pharmaceuticals and metabolites in 24 Minnesota rivers and wastewaters.  |  Writer, JH., et al. 2013. Sci Total Environ. 461-462: 519-27. PMID: 23751335
  9. Differences in cytochrome p450-mediated pharmacokinetics between chinese and caucasian populations predicted by mechanistic physiologically based pharmacokinetic modelling.  |  Barter, ZE., et al. 2013. Clin Pharmacokinet. 52: 1085-100. PMID: 23818090
  10. A sensitive and high-throughput LC-MS/MS method for inhibition assay of seven major cytochrome P450s in human liver microsomes using an in vitro cocktail of probe substrates.  |  Liu, LY., et al. 2015. Biomed Chromatogr. 29: 437-44. PMID: 25098274
  11. Evaluation of metabolism dependent inhibition of CYP2B6 mediated bupropion hydroxylation in human liver microsomes by monoamine oxidase inhibitors and prediction of potential as perpetrators of drug interaction.  |  Nirogi, R., et al. 2015. Chem Biol Interact. 230: 9-20. PMID: 25656918
  12. The effect of chronic kidney disease on CYP2B expression and activity in male Wistar rats.  |  Kucey, AS., et al. 2019. Pharmacol Res Perspect. 7: e00475. PMID: 31049204
  13. Do the lockdown-imposed changes in a wastewater treatment plant catchment's socio-demographics impact longitudinal temporal trends in psychoactive pharmaceutical use?  |  Boogaerts, T., et al. 2023. Sci Total Environ. 876: 162342. PMID: 36842581
  14. Evidence that the acute behavioral and electrophysiological effects of bupropion (Wellbutrin) are mediated by a noradrenergic mechanism.  |  Cooper, BR., et al. 1994. Neuropsychopharmacology. 11: 133-41. PMID: 7840865
  15. Pharmacokinetics of bupropion and its metabolites in cigarette smokers versus nonsmokers.  |  Hsyu, PH., et al. 1997. J Clin Pharmacol. 37: 737-43. PMID: 9378846

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Hydroxy Bupropion, 10 mg

sc-211604
10 mg
$266.00