An active metabolite of bupropion
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S,S-hydroxy Bupropion (hydrochloride)

Item No. 35718

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol, monohydrochloride
CAS Number
106083-71-0
Synonyms
  • BUPOH
  • BW 306U
  • GW 353162A
  • Radafaxine
Molecular Formula
C13H18ClNO2 • HCl
Formula Weight
292.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
SMILES
O[C@]1(C2=CC(Cl)=CC=C2)[C@@H](NC(C)(CO1)C)C.Cl
InChi Code
InChI=1S/C13H18ClNO2.ClH/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;1H/t9-,13+;/m0./s1
InChi Key
ORXTVTDGPVINDN-BTJVGWIPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $32

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    5 mg

    $141

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    10 mg

    $248

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    25 mg

    $542

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    Product Description

    S,S-hydroxy Bupropion is an active metabolite of the antidepressant bupropion.1,2 It is formed from bupropion by the cytochrome P450 (CYP) isoform CYP2B6.3 S,S-hydroxy Bupropion inhibits dopamine and norepinephrine but not serotonin (5-HT) reuptake in HEK293 cells expressing the human transporters (IC50s = 0.63, 0.241, and >100 µM, respectively).1 It is also an antagonist of α3β4-, α4β2-, α4β4-, and α1β1 subunit-containing nicotinic acetylcholine receptors (nAChRs; IC50s = 11, 3.3, 30, and 28 µM, respectively). S,S-hydroxy Bupropion inhibits nicotine-induced analgesia in the tail-flick and hot plate tests, hyperlocomotion, and hypothermia in mice (ED50s = 0.2, 1, 0.9, and 1.5 mg/kg, respectively). It substitutes for (+)-amphetamine in rats in a two-lever drug discrimination test (ED50 = 4.4 mg/kg).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lukas, R.J., Muresan, A.Z., Damaj, M.I., et al. Synthesis and characterization of in vitro and in vivo profiles of hydroxybupropion analogues: Aids to smoking cessation. J. Med. Chem. 53(12), 4731-4748 (2010).

    2. Bondarev, M.L., Bondareva, T.S., Young, R., et al. Behavioral and biochemical investigations of bupropion metabolites. Eur. J. Pharmacol. 474(1), 85-93 (2003).

    3. Coles, R., and Kharasch, E.D. Stereoselective metabolism of bupropion by cytochrome P4502B6 (CYP2B6) and human liver microsomes. Pharm. Res. 25(6), 1405-1411 (2008).