(2R,3R)-3-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-2-phenylpiperidine hydrochloride

• ChemBase ID: 131379
• Molecular Formular: C20H20ClF6NO
• Molecular Mass: 439.8223192
• Monoisotopic Mass: 439.11376127
• SMILES: c1ccc(cc1)[C@@H]1[C@@H](CCCN1)OCc1cc(cc(c1)C(F)(F)F)C(F)(F)F.Cl
• Canonical SMILES: FC(c1cc(CO[C@@H]2CCCN[C@@H]2c2ccccc2)cc(c1)C(F)(F)F)(F)F.Cl
• InChI: InChI=1S/C20H19F6NO.ClH/c21-19(22,23)15-9-13(10-16(11-15)20(24,25)26)12-28-17-7-4-8-27-18(17)14-5-2-1-3-6-14;/h1-3,5-6,9-11,17-18,27H,4,7-8,12H2;1H/t17-,18-;/m1./s1
• InChIKey: DYEUTIUITGHIEO-JAXOOIEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-3-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-2-phenylpiperidine hydrochloride
• IUPAC Traditional name: (2R,3R)-3-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-2-phenylpiperidine hydrochloride
• Synonyms: (2S,3S)-3-[(3,5-bis(Trifluoromethyl)phenyl)methoxy]-2-phenylpiperidine hydrochloride; L-733,060 hydrochloride; (2R,3R)-3-[(3,5-bis(Trifluoromethyl)phenyl)methoxy]-2-phenylpiperidine hydrochloride; L-733,061 hydrochloride

Database IDs

• CAS Number: 148687-76-7
• MDL Number: MFCD06798982
• PubChem SID: 162225657; 24896280; 24278530
• PubChem CID: 11568371

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.4140062
• LogD (pH = 7.4): 3.8186169
• Log P: 5.490121
• Molar Refractivity: 93.7909 cm^3
• Polarizability: 34.66278 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... TACR1(6869)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - L137

Legal Information
Manufactured and sold under license from Merck, Sharp and Dohme Ltd.
Biochem/physiol Actions
Non-peptide NK1 tachykinin receptor antagonist; selective for guinea pig/human versus rat/mouse. Micromolar concentrations of L-733,060 inhibit the growth of human gastric and colon adenocarcinomas.in a dose-dependent manner, eventually leading to apoptosis in both cell lines.1

Sigma Aldrich - L138

Biochem/physiol Actions
Weak NK-1 tachykinin receptor antagonist; less active enantiomer of L-733,060 hydrochloride.
Legal Information
Manufactured and sold under license from Merck, Sharp and Dohme Ltd.