1-(3,4-dihydroxyphenyl)-2-(methylamino)ethane-1-sulfonic acid

• ChemBase ID: 168091
• Molecular Formular: C9H13NO5S
• Molecular Mass: 247.26822
• Monoisotopic Mass: 247.05144352
• SMILES: c1(c(ccc(c1)C(CNC)S(=O)(=O)O)O)O
• Canonical SMILES: CNCC(S(=O)(=O)O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C9H13NO5S/c1-10-5-9(16(13,14)15)6-2-3-7(11)8(12)4-6/h2-4,9-12H,5H2,1H3,(H,13,14,15)
• InChIKey: TYYGQMPOZGEFQL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3,4-dihydroxyphenyl)-2-(methylamino)ethane-1-sulfonic acid
• IUPAC Traditional name: 1-(3,4-dihydroxyphenyl)-2-(methylamino)ethanesulfonic acid
• Synonyms: 3,4-Dihydroxy-α-[(methylamino)methyl]benzenemethanesulfonic Acid; 3,4-Dihydroxy-α-[(methylamino)methyl]-α-toluenesulfonic Acid; Epinephrine Sulfonic Acid

Database IDs

• CAS Number: 26405-77-6
• PubChem SID: 162262223
• PubChem CID: 13505616

CALCULATED PROPERTIES

• Acid pKa: -1.8051196
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.0618868
• LogD (pH = 7.4): -1.0756588
• Log P: -1.0617156
• Molar Refractivity: 57.7481 cm^3
• Polarizability: 23.317966 Å^3
• Polar Surface Area: 106.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO (Sparingly); Water
• Apperance: Beige Solid
• Melting Point: >220°C *dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - E588605

An Epinephrine (E588585) derivative formed in injection solutions and eye drops during sterilization and storage of L-Epinephrine Bitartrate.

REFERENCES

• De Mol, N.J. et al.: Pharmac. Week., 117, 1 (1982)
• Liu, C. et al.: Yao. Fen. Zaz., 2, 200 (1982)