Threohydrobupropion

Threohydrobupropion
Clinical data
(1S,2S)-Threohydrobupropion
Other names	threo-Hydrobupropion; Threohydroxybupropion; BW 494; BW A494U; threo-3-Chloro-N-tert-butyl-β-hydroxy-α-methylphenethylamine; threo-3-Chloro-N-tert-butyl-β-hydroxyamphetamine
Pharmacokinetic data
Protein binding	42%
Metabolism	Hydroxylation (CYP2B6, CYP2C19), glucuronidation (UGTs)
Elimination half-life	37 hours
Identifiers
IUPAC name rel-(1R^,2R^)-2-(tert-Butylamino)-1-(3-chlorophenyl)propan-1-ol
CAS Number	92264-82-9^Y (racemate) 153365-82-3 (R,R) 102141-12-8 (S,S)
PubChem CID	9943534
ChemSpider	8010403
UNII	988C8SFV4F
ChEMBL	ChEMBL1304
CompTox Dashboard (EPA)	DTXSID70431488
ECHA InfoCard	100.216.731
Chemical and physical data
Formula	C₁₃H₂₀ClNO
Molar mass	241.76 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [C@H]([C@@H](NC(C)(C)C)C)(O)C1=CC(Cl)=CC=C1
InChI InChI=1/C13H20ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,12,15-16H,1-4H3/t9-,12+/s2 Key:NDPTTXIBLSWNSF-JVMLCUHDNA-N

Threohydrobupropion (developmental code names BW 494, BW A494U) is a substituted amphetamine derivative—specifically a β-hydroxyamphetamine—and a major active metabolite of the antidepressant drug bupropion (Wellbutrin). Bupropion is a norepinephrine–dopamine reuptake inhibitor and nicotinic acetylcholine receptor negative allosteric modulator, with its metabolites contributing substantially to its activities.