Hydroxybupropion is a major metabolite of Bupropion (trade names Wellbutrin and Zyban) which is a marketed antidepressant and a smoking cessation drug.
Physicochemical Properties
| Molecular Formula | C₁₃H₁₈CLNO₂ |
| Molecular Weight | 255.74 |
| Exact Mass | 255.103 |
| CAS # | 92264-81-8 |
| Related CAS # | Bupropion morpholinol; 357399-43-0; Bupropion morpholinol-d6; 1216893-18-3; Radafaxine; 192374-14-4 |
| PubChem CID | 446 |
| Appearance | White to off-white solid |
| Density | 1.15 g/cm3 |
| Boiling Point | 393.9ºC at 760 mmHg |
| Melting Point | 121-123ºC |
| Flash Point | 192ºC |
| LogP | 2.662 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 17 |
| Complexity | 268 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=C(C(C)NC(CO)(C)C)C1C=C(Cl)C=CC=1 |
| InChi Key | AKOAEVOSDHIVFX-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C13H18ClNO2/c1-9(15-13(2,3)8-16)12(17)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3 |
| Chemical Name | 1-(3-chlorophenyl)-2-[(1-hydroxy-2-methylpropan-2-yl)amino]propan-1-one |
| Synonyms | Hydroxybupropion |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | nACh receptor; Norepinephrine uptake ( IC50 = 1.7 μM ) |
| ln Vivo | The concentration of hydroxybupropion greatly exceeds the concentration of the parent drug, reaching 10 to 100 times the concentration of bupropion. Hydroxybupropion exhibits greater anti-bupropion activity (indicating antidepressant activity in animals) and has pharmacological activity than erythro- and threo-hydroxybupropion, inhibiting solutions of norbenazol and dopamine, Antagonizes nicotine and exhibits antidepressant effects in rodents [1]. |
| References |
[1]. Enantioselective effects of hydroxy metabolites of bupropion on behavior and on function of monoamine transporters and nicotinic receptors. Mol Pharmacol. 2004 Sep;66(3):675-82. |
| Additional Infomation | Hydroxybupropion is an aromatic ketone. |
Solubility Data
| Solubility (In Vitro) | DMSO: ~100 mg/mL (~391.0 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.78 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.78 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (9.78 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9102 mL | 19.5511 mL | 39.1022 mL | |
| 5 mM | 0.7820 mL | 3.9102 mL | 7.8204 mL | |
| 10 mM | 0.3910 mL | 1.9551 mL | 3.9102 mL |