4-(2-aminoethyl)-2-sulfanylphenol hydrochloride

• ChemBase ID: 172788
• Molecular Formular: C8H12ClNOS
• Molecular Mass: 205.70498
• Monoisotopic Mass: 205.03281269
• SMILES: c1c(c(cc(c1)CCN)S)O.Cl
• Canonical SMILES: NCCc1ccc(c(c1)S)O.Cl
• InChI: InChI=1S/C8H11NOS.ClH/c9-4-3-6-1-2-7(10)8(11)5-6;/h1-2,5,10-11H,3-4,9H2;1H
• InChIKey: YPPBZPYBTMVFNW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-aminoethyl)-2-sulfanylphenol hydrochloride
• IUPAC Traditional name: 4-(2-aminoethyl)-2-sulfanylphenol hydrochloride
• Synonyms: 4-(2-Aminoethyl)-2-mercaptophenol Hydrochloride; 3-Mercaptotyramine Hydrochloride

Database IDs

• CAS Number: 37736-93-9
• PubChem SID: 164228698
• PubChem CID: 71437312

CALCULATED PROPERTIES

• Acid pKa: 6.196839
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 0.14523375
• LogD (pH = 7.4): 0.89033914
• Log P: 0.905774
• Molar Refractivity: 49.2771 cm^3
• Polarizability: 19.109726 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off White Solid
• Melting Point: 182-185°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Sensitive to Oxidation

DETAILS

Toronto Research Chemicals - M257500

3-Mercaptotyramine, the mercapto analog of dopamine, irreversibly inhibits the enzyme, catechol-O-methyltransferase, presumably by the formation of an SS bridge to a reactive mercapto group in the reactive site.

REFERENCES

• Lutz, W.B., et al.: J. Med. Chem., 15, 795 (1972)