(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol hydrochloride

• ChemBase ID: 154967
• Molecular Formular: C13H19Cl2NO2
• Molecular Mass: 292.20146
• Monoisotopic Mass: 291.07928421
• SMILES: C[C@H]1[C@@](OCC(N1)(C)C)(c1cccc(c1)Cl)O.Cl
• Canonical SMILES: Clc1cccc(c1)[C@]1(O)OCC(N[C@H]1C)(C)C.Cl
• InChI: 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
• InChIKey: ORXTVTDGPVINDN-BTJVGWIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol hydrochloride
• IUPAC Traditional name: radafaxine hydrochloride
• Synonyms: (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride; (2S,3S)-2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride; (2S,3S)-Hydroxybupropion hydrochloride; GW 353162; Radafaxine hydrochloride; SS-hydroxybupropion hydrochloride; (2S,3S)-Hydroxybupropion hydrochloride

Database IDs

• CAS Number: 106083-71-0
• MDL Number: MFCD10565921
• PubChem SID: 162249105
• PubChem CID: 9838996

CALCULATED PROPERTIES

• Acid pKa: 10.754683
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.81730276
• LogD (pH = 7.4): 2.479874
• Log P: 2.9009485
• Molar Refractivity: 67.7986 cm^3
• Polarizability: 27.185991 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥12 mg/mL
• Apperance: white to tan powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H18ClNO2 · HCl

DETAILS

Sigma Aldrich - H3167

Biochem/physiol Actions
(2S,3S)-hydroxybupropion is a DAT (dopamine transporter) and NET(norepinephrine transporter) transporters inhibitor, and nAChR family modulator. (2S,3S)-hydroxybupropion is a major metabolite of bupropion. Hydroxybupropions were reported to contribute to antidepressant and perhaps smoking cessation activities. Both (2S,3S) and (2R,3R) metabolites reverse affective and somatic withdrawal signs in nicotine-dependent mice, but (2S,3S)-hydroxybupropion is more potent. (2S,3S)-hydroxybupropion significantly decreases the development of nicotine reward in mice.