1-(3,4-dihydroxyphenyl)-2-(methylamino)ethan-1-one

• ChemBase ID: 179838
• Molecular Formular: C9H11NO3
• Molecular Mass: 181.18854
• Monoisotopic Mass: 181.07389322
• SMILES: c1(cc(c(cc1)O)O)C(=O)CNC
• Canonical SMILES: CNCC(=O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C9H11NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,10-12H,5H2,1H3
• InChIKey: PZMVOUYYNKPMSI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3,4-dihydroxyphenyl)-2-(methylamino)ethan-1-one
• IUPAC Traditional name: 1-(3,4-dihydroxyphenyl)-2-(methylamino)ethan-1-one
• Synonyms: Adrenon; Chemosan; Damazor; Haemodan; Kephrine; Ketogaze; Remestyp; Stryphnon; Stypnon; Adrenalone

Database IDs

• CAS Number: 99-45-6
• PubChem SID: 164235748
• PubChem CID: 7436

CALCULATED PROPERTIES

• Acid pKa: 7.4984984
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.8581022
• LogD (pH = 7.4): -0.28453013
• Log P: -0.17845818
• Molar Refractivity: 48.5569 cm^3
• Polarizability: 18.655052 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Sympathomimetic-Alpha; Vasoconstrictor

Product Information

• Application(s): Haemostatic; Shows similar physiological activity to Adrenaline FDN25-T

REFERENCES

• Stolz, F., Ber., 1904, 37, 4152
• Friedmann, E., Chem. Zentralbl., 1906, 1, 1620, (synth)
• Lands, A.M. et al., J. Pharmacol. Exp. Ther., 1948, 92, 369, (pharmacol)
• Ravina, A. et al., Therapie, 1953, 8, 224, (props, use)
• Biniecki, S. et al., Acta Pol. Pharm., 1963, 20, 245, (synth)
• Bergin, R., Acta Cryst. B, 1971, 27, 2139, (cryst struct)
• Hussain, A. et al., J. Pharm. Sci., 1976, 65, 1510, (deriv)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1240
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MGC350