Threohydrobupropion

Threohydrobupropion
	(1S,2S)-Threohydrobupropion
Clinical data
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 (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).^[1]^[2] Bupropion is a norepinephrine–dopamine reuptake inhibitor and nicotinic acetylcholine receptor negative allosteric modulator, with its metabolites contributing substantially to its activities.^[1]

^ ^a ^b ^c ^d ^e Costa R, Oliveira NG, Dinis-Oliveira RJ (August 2019). "Pharmacokinetic and pharmacodynamic of bupropion: integrative overview of relevant clinical and forensic aspects". Drug Metab Rev. 51 (3): 293–313. doi:10.1080/03602532.2019.1620763. PMID 31124380. S2CID 163167323.
^ ^a ^b Jefferson JW, Pradko JF, Muir KT (November 2005). "Bupropion for major depressive disorder: Pharmacokinetic and formulation considerations". Clin Ther. 27 (11): 1685–95. doi:10.1016/j.clinthera.2005.11.011. PMID 16368442.