methyl({2-[(2-methylphenyl)(phenyl)methoxy]ethyl})amine

• ChemBase ID: 129939
• Molecular Formular: C17H21NO
• Molecular Mass: 255.35474
• Monoisotopic Mass: 255.1623143
• SMILES: O(CCNC)C(c1ccccc1)c1ccccc1C
• Canonical SMILES: CNCCOC(c1ccccc1C)c1ccccc1
• InChI: InChI=1S/C17H21NO/c1-14-8-6-7-11-16(14)17(19-13-12-18-2)15-9-4-3-5-10-15/h3-11,17-18H,12-13H2,1-2H3
• InChIKey: PNYKGCPSFKLFKA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl({2-[(2-methylphenyl)(phenyl)methoxy]ethyl})amine
• IUPAC Traditional name: tofenacin
• Synonyms: N-Methyl-2-[(2-methylphenyl)phenylmethoxy]ethanamine; N-Methyl-2-[(o-methyl-α-phenylbenzyl)oxy]ethylamine; Demethylorphenadrine; N-Demethylorphenadrine; N-Desmethylorphenadrine; Tofenacine; Tofenacin

Database IDs

• CAS Number: 15301-93-6
• PubChem SID: 162224225
• PubChem CID: 25315
• Chemspider ID: 23647
• Wikipedia Title: Tofenacin

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.58734125
• LogD (pH = 7.4): 1.542377
• Log P: 3.7822807
• Molar Refractivity: 79.6735 cm^3
• Polarizability: 31.324652 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Semi-Solid

Pharmacology Properties

• Legal Status: Rx-only

DETAILS

Toronto Research Chemicals - T528500

A metabolite of Orphenadrine (O695300). An antidepressant prodrug.

REFERENCES

• Watkins, P., et al.: J. Biol. Chem., 261, 6264 (1986)
• McNeil, C., et al.: Biochem. Pharmacol., 51, 15 (1986)
• Hiessbock, R., et al.: J. Med. Chem., 42, 1921 (1986)