2-diphenylmethanesulfinylacetamide

• ChemBase ID: 174671
• Molecular Formular: C15H15NO2S
• Molecular Mass: 273.3501
• Monoisotopic Mass: 273.08234973
• SMILES: c1ccccc1C([S@](=O)CC(=O)N)c1ccccc1
• Canonical SMILES: NC(=O)C[S@@](=O)C(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)/t19-/m1/s1
• InChIKey: YFGHCGITMMYXAQ-LJQANCHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-diphenylmethanesulfinylacetamide
• IUPAC Traditional name: modafinil
• Synonyms: 2-[(R)-(diphenylmethyl)sulfinyl]acetamide; (-)-Modafinil; (R)-(-)-Modafinil; Armodafinil; (R)-Modafinil

Database IDs

• CAS Number: 112111-43-0
• PubChem SID: 164230581
• PubChem CID: 9690109

CALCULATED PROPERTIES

• Acid pKa: 8.8397665
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.5326362
• LogD (pH = 7.4): 1.517359
• Log P: 1.5328344
• Molar Refractivity: 77.3886 cm^3
• Polarizability: 30.265642 Å^3
• Polar Surface Area: 60.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 153-155°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M482505

Used for treatment of excessive sleepiness, α1-adrenoceptor agonist.

REFERENCES

• Saletu, B., et al.: Int. J. Clin. Pharmacol. Res., 9, 183 (1989)
• Chemelli, R.M., et al.: Cell, 98, 437 (1989)
• Purnell, M., et al.: J. Sleep Res., 11, 219 (1989)
• Dinges, D., et al.: Curr. Med. Res. Opin., 22, 159 (2006)