4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol hydrochloride

• ChemBase ID: 153882
• Molecular Formular: C16H26ClNO2
• Molecular Mass: 299.83614
• Monoisotopic Mass: 299.16520676
• SMILES: CN(C)CC(c1ccc(cc1)O)C1(CCCCC1)O.Cl
• Canonical SMILES: CN(CC(C1(O)CCCCC1)c1ccc(cc1)O)C.Cl
• InChI: InChI=1S/C16H25NO2.ClH/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16;/h6-9,15,18-19H,3-5,10-12H2,1-2H3;1H
• InChIKey: IMWPSXHIEURNKZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol hydrochloride
• IUPAC Traditional name: desvenlafaxine hydrochloride
• Synonyms: 4-[2-(Dimethylamino)-1-(1-Hydroxycyclohexyl)Ethyl]-Phenol Hydrochloride; Desvenlafaxine hydrochloride; Desvenlafaxine Hydrochloride

Database IDs

• CAS Number: 300827-87-6
• MDL Number: MFCD11045287
• PubChem SID: 162248021
• PubChem CID: 25268065

CALCULATED PROPERTIES

• Acid pKa: 10.111714
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.5600763
• LogD (pH = 7.4): 1.0721254
• Log P: 2.2934265
• Molar Refractivity: 78.5419 cm^3
• Polarizability: 30.689209 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL; H2O: >20 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H25NO2 · HCl

DETAILS

Sigma Aldrich - D2069

Biochem/physiol Actions
Desvenlafaxine hydrochloride is a dual SERT/NET reuptake inhibitor. It is a major active metabolite of venlafaxine (#542); brain penetrant; Ki = 40 nM and 122 nM for hSERT and hNET, respectively (weak binding at the hDAT). Inhibition of [3H]5-HT or [3H]NE uptake for the hSERT or hNET produced IC50 values of 47 and 531 nM.