5-(dimethylamino)-N-[2-(methanesulfonylsulfanyl)ethyl]naphthalene-1-sulfonamide

• ChemBase ID: 154093
• Molecular Formular: C15H20N2O4S3
• Molecular Mass: 388.5253
• Monoisotopic Mass: 388.05852013
• SMILES: CN(C)c1cccc2c1cccc2S(=O)(=O)NCCSS(=O)(=O)C
• Canonical SMILES: CN(c1cccc2c1cccc2S(=O)(=O)NCCSS(=O)(=O)C)C
• InChI: InChI=1S/C15H20N2O4S3/c1-17(2)14-8-4-7-13-12(14)6-5-9-15(13)24(20,21)16-10-11-22-23(3,18)19/h4-9,16H,10-11H2,1-3H3
• InChIKey: ZKELPZYUWUFQLZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(dimethylamino)-N-[2-(methanesulfonylsulfanyl)ethyl]naphthalene-1-sulfonamide
• IUPAC Traditional name: 5-(dimethylamino)-N-[2-(methanesulfonylsulfanyl)ethyl]naphthalene-1-sulfonamide
• Synonyms: 2-(5-Dimethylamino1-naphthylsulfonamido)ethyl methanethiosulfonate; MTS-Dansyl; Dansylamidoethyl methanethiosulfonate; 2-(5-Dimethylaminonaphth-1-ylsulfonamido)ethyl Methanethiosulfonate; Methanesulfonothioic Acid S-[2-[[[5-(Dimethylamino)-1-naphthalenyl]sulfonyl]amino]ethyl]ester; Dansylamidoethyl Methanethiosulfonate

Database IDs

• CAS Number: 355115-41-2
• PubChem SID: 162248232
• PubChem CID: 3307199

CALCULATED PROPERTIES

• Acid pKa: 9.911227
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.3580209
• LogD (pH = 7.4): 1.4108603
• Log P: 1.4127781
• Molar Refractivity: 99.6455 cm^3
• Polarizability: 40.767265 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichlormethane; DMSO; Ethyl Acetate; Methanol
• Apperance: Yellow Solid
• Melting Point: 94-97°C
• Fluorescence: λem 510-530 nm

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥75.0% (coupling rate)
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C15H20N2O4S3

DETAILS

Toronto Research Chemicals - D173500

Reacts specifically and rapidly with thiols to form mixed disulfides. Used to probe the structures of the ACh receptor channel, the GABAA receptor channel, and lactose permease.Fluorescence: max. Abs. 335nm; max. Em. 526nm; e x 10-3: 4.1

REFERENCES

• Xu, M., et al.: J. Biol. Chem., 268, 21505 (1993)
• Duhten, R.L., et al.: Biochemistry, 32, 3139 (1993)
• Yang, N. et al.: Neuron., 16, 113 (1993)