(2R,3R)-Hydroxybupropion

(2R,3R)-Hydroxybupropion
Clinical data
Other names	(R,R)-Hydroxybupropion
Pharmacokinetic data
Metabolism	Glucuronidation
Metabolites	Hydroxybupropion glucuronide
Elimination half-life	19–26 hours
Identifiers
	IUPAC name (2R,3R)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol;
CAS Number	192374-15-5;
PubChem CID	9943908;
ChemSpider	8119520;
ChEMBL	ChEMBL1172929;
CompTox Dashboard (EPA)	DTXSID40433176 ;
Chemical and physical data
Formula	C13H18ClNO2
Molar mass	255.74 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1[C@](OCC(N1)(C)C)(C2=CC(=CC=C2)Cl)O;
	InChI InChI=1S/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; Key:RCOBKSKAZMVBHT-RNCFNFMXSA-N;

(2R,3R)-Hydroxybupropion, or simply (R,R)-hydroxybupropion, is the major metabolite of the antidepressant, smoking cessation, and appetite suppressant medication bupropion. It is the (2R,3R)-enantiomer of hydroxybupropion, which in humans occurs as a mixture of (2R,3R)-hydroxybupropion and (2S,3S)-hydroxybupropion (radafaxine). Hydroxybupropion is formed from bupropion mainly by the cytochrome P450 enzyme CYP2B6. Levels of (2R,3R)-hydroxybupropion are dramatically higher than those of bupropion and its other metabolites during bupropion therapy.