ethyl (1R,2R)-2-[(2H3)methylamino]-1-phenylcyclohex-3-ene-1-carboxylate hydrochloride

• ChemBase ID: 175722
• Molecular Formular: C16H22ClNO2
• Molecular Mass: 295.80438
• Monoisotopic Mass: 295.13390663
• SMILES: C1=CCC[C@@]([C@@H]1NC)(C(=O)OCC)c1ccccc1.Cl
• Canonical SMILES: CCOC(=O)[C@]1(CCC=C[C@H]1NC)c1ccccc1.Cl
• InChI: InChI=1S/C16H21NO2.ClH/c1-3-19-15(18)16(13-9-5-4-6-10-13)12-8-7-11-14(16)17-2;/h4-7,9-11,14,17H,3,8,12H2,1-2H3;1H/t14-,16-;/m1./s1
• InChIKey: REPHWVDUMWCCKC-VNYZMKMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (1R,2R)-2-[(^2H₃)methylamino]-1-phenylcyclohex-3-ene-1-carboxylate hydrochloride
• IUPAC Traditional name: ethyl (1R,2R)-2-[(^2H₃)methylamino]-1-phenylcyclohex-3-ene-1-carboxylate hydrochloride
• Synonyms: trans-2-(Methyl-d3)amino-1-phenyl-3-cyclohexene-1-carboxylic Acid Ethyl Ester Hydrochloride; Nortilidine-d3 Hydrochloride

Database IDs

• CAS Number: 1217648-75-3
• PubChem SID: 164231632
• PubChem CID: 71751250

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.030447962
• LogD (pH = 7.4): 1.4909406
• Log P: 2.9715502
• Molar Refractivity: 76.8698 cm^3
• Polarizability: 30.071012 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 208-210°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - N831002

The labelled active metabolite of Tilidine. A receptor antagonist. Nortilidine easily penetrates the blood-brain barrier and activates the μ-opioid receptor. The enzymes involved in Tilidine metabolism are unknown.

REFERENCES

• Boesch, D., et al.: Cancer Res., 51, 4226 (1991)
• Austin, R., et al.: Drug Metab. Dispos., 30, 1497 (1991)
• Hajda, J., et al.: J. Clin. Pharmacol., 42, 1257 (1991)
• Thierry, C., et al.: Eur. J. Pharmacol., 506, 205 (1991)