oxalic acid methyl (3R,4S)-3-methyl-1-(2-phenylethyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate

• ChemBase ID: 172363
• Molecular Formular: C27H34N2O7
• Molecular Mass: 498.56806
• Monoisotopic Mass: 498.23660144
• SMILES: C1C[C@@]([C@@H](CN1CCc1ccccc1)C)(N(c1ccccc1)C(=O)CC)C(=O)OC.C(=O)(O)C(=O)O
• Canonical SMILES: OC(=O)C(=O)O.CCC(=O)N([C@]1(CCN(C[C@H]1C)CCc1ccccc1)C(=O)OC)c1ccccc1
• InChI: InChI=1S/C25H32N2O3.C2H2O4/c1-4-23(28)27(22-13-9-6-10-14-22)25(24(29)30-3)16-18-26(19-20(25)2)17-15-21-11-7-5-8-12-21;3-1(4)2(5)6/h5-14,20H,4,15-19H2,1-3H3;(H,3,4)(H,5,6)/t20-,25+;/m1./s1
• InChIKey: CBKLICUQYUTWQL-NLEDUAFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: oxalic acid methyl (3R,4S)-3-methyl-1-(2-phenylethyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate
• IUPAC Traditional name: lofentanil; oxalic acid
• Synonyms: (3R,4S)-rel-(-)-3-Methyl-4-[(1-oxopropyl)phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylic Acid Ethanedioate; (-)-cis-3-Methyl-1-phenethyl-4 -(N-phenyl-propionamido)isonipecotic Acid Methyl Ester Oxalate; R 34995; Lofentanil Oxalate

Database IDs

• CAS Number: 61380-41-4
• PubChem SID: 164228273
• PubChem CID: 20055412

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.3782328
• LogD (pH = 7.4): 3.1458476
• Log P: 4.146847
• Molar Refractivity: 118.7924 cm^3
• Polarizability: 46.549965 Å^3
• Polar Surface Area: 49.85 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 84-86°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - L469370

Analgesic (narcotic).Controlled Substance.

REFERENCES

• Stahl, K.D., et al.: Eur. J. Pharmacol., 46, 199 (1977)
• Janssen, P., et al.: Life Sci., 31, 457 (1977)