3-methyl-4-(morpholin-4-yl)-2,2-diphenyl-1-(pyrrolidin-1-yl)butan-1-one

• ChemBase ID: 1316
• Molecular Formular: C25H32N2O2
• Molecular Mass: 392.53378
• Monoisotopic Mass: 392.24637827
• SMILES: O=C(N1CCCC1)C(C(CN1CCOCC1)C)(c1ccccc1)c1ccccc1
• Canonical SMILES: CC(C(C(=O)N1CCCC1)(c1ccccc1)c1ccccc1)CN1CCOCC1
• InChI: InChI=1S/C25H32N2O2/c1-21(20-26-16-18-29-19-17-26)25(22-10-4-2-5-11-22,23-12-6-3-7-13-23)24(28)27-14-8-9-15-27/h2-7,10-13,21H,8-9,14-20H2,1H3
• InChIKey: INUNXTSAACVKJS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-4-(morpholin-4-yl)-2,2-diphenyl-1-(pyrrolidin-1-yl)butan-1-one
• IUPAC Traditional name: dextromoramide tartrate; dauran
• Synonyms: Dextromoramide; 3-Methyl-4-(4-morpholinyl)-2,2-diphenyl-1-(1-pyrrolidinyl)-1-butanone; 1-[3-Methyl-4-(4-morpholinyl)-1-oxo-2,2-diphenylbutyl]-pyrrolidine; (±)-4-[2-Methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl]morpholine; R 610; Racemoramide; rac-Moramide

Database IDs

• CAS Number: 545-59-5; 357-56-2
• PubChem SID: 46507896; 160964776
• PubChem CID: 9648

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.5076978
• LogD (pH = 7.4): 3.2307322
• Log P: 3.7531147
• Molar Refractivity: 117.3748 cm^3
• Polarizability: 45.848522 Å^3
• Polar Surface Area: 32.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.18
• LOG S: -4.35
• Solubility (Water): 1.75e-02 g/l

DETAILS

DrugBank - DB01529

• Drug Groups: illicit; experimental
• Description: An opioid analgesic structurally related to methadone and used in the treatment of severe pain. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1070)
• External Links: Wikipedia

Toronto Research Chemicals - M630200

The racemic Moramide. (S)-Moramide or Dextromoramide is a controlled substance (opiate). Analgesic (narcotic).

REFERENCES

• Aoyama, T., et al.: J. Pharm. Sci., 79, 465 (1990)
• Decamp, W., et al.: J. Pharm. Biomed. Anal., 11, 1167 (1990)