2-diphenylmethanesulfinyl-N-hydroxyacetamide

• ChemBase ID: 153193
• Molecular Formular: C15H15NO3S
• Molecular Mass: 289.3495
• Monoisotopic Mass: 289.07726435
• SMILES: c1ccc(cc1)C(c1ccccc1)S(=O)CC(=O)NO
• Canonical SMILES: ONC(=O)CS(=O)C(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C15H15NO3S/c17-14(16-18)11-20(19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15,18H,11H2,(H,16,17)
• InChIKey: CGNMLOKEMNBUAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-diphenylmethanesulfinyl-N-hydroxyacetamide
• IUPAC Traditional name: adrafinil
• Synonyms: 2-[(Diphenylmethyl)sulfinyl]acetohydroxamic acid; CRL 40028; Olmifon; Adrafinil; 2-[(Diphenylmethyl)sulfinyl]-N-hydroxyacetamide; 2-(Benzhydrylsulfinyl)acetohydroxamic Acid; Adrafinil

Database IDs

• CAS Number: 63547-13-7
• EC Number: 264-303-1
• MDL Number: MFCD00865357
• PubChem SID: 24890429; 162247332
• PubChem CID: 3033226

CALCULATED PROPERTIES

• Acid pKa: 8.104461
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.5285765
• LogD (pH = 7.4): 1.4515502
• Log P: 1.5296527
• Molar Refractivity: 79.1532 cm^3
• Polarizability: 30.885447 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble35 mg/mL; Methanol; Water
• Apperance: Light Pink Solid; white solid
• Melting Point: 159-160°C

Safety Information

• Storage Condition: -20°C Freezer; desiccated
• RTECS: AB8139500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H15NO3S

DETAILS

Sigma Aldrich - A0479

Biochem/physiol Actions
Agent promoting wakefulness; analog of Modafinil.
Caution
Hygroscopic

Toronto Research Chemicals - A301500

α-Adrenergic agonist. Treatment of depression.

REFERENCES

• Duteil, J., et al.: Eur. J. Pharmacol., 59, 121 (1979)
• Roze, C., et al.: Arch. Int. Pharmacodyn. Ther., 265, 119 (1979)
• Rambert, F.A., et al.: J. Pharmacol., 17, 37 (1979)