4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol

• ChemBase ID: 179851
• Molecular Formular: C9H13NO2
• Molecular Mass: 167.20502
• Monoisotopic Mass: 167.09462866
• SMILES: c1(ccc(cc1)O)[C@H](O)CNC
• Canonical SMILES: CNC[C@H](c1ccc(cc1)O)O
• InChI: InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3
• InChIKey: YRCWQPVGYLYSOX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
• IUPAC Traditional name: 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
• Synonyms: Oxedrine; Analeptin; Ethaphene; Simpalon; Sympathol; Synephrine

Database IDs

• CAS Number: 94-07-5
• PubChem SID: 164235761
• PubChem CID: 667452

CALCULATED PROPERTIES

• Acid pKa: 9.755471
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.5592577
• LogD (pH = 7.4): -1.3917326
• Log P: -0.0709516
• Molar Refractivity: 47.2494 cm^3
• Polarizability: 18.594215 Å^3
• Polar Surface Area: 52.49 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: alpha1-Adrenergic agonist; beta3-Adrenergic agonist

Product Information

• Biological Source: Alkaloid from a number of Coryphantha spp. and from Dolichothele longimamma (Cactaceae)
• Application(s): Possesses decongestant props.; Promotes weight loss; Sympathomimetic agent showing vasoconstrictor, hypertensive and bronchial muscle relaxant props.

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 613C, (nmr)
• Priestley, H.M. et al., J.O.C., 1940, 5, 355, (synth)
• Corrigan, J.R. et al., J.A.C.S., 1945, 67, 1894, (synth)
• Stewart, I.S. et al., J. Biol. Chem., 1964, 239, 930, (isol)
• Kappe, T. et al., J. Med. Chem., 1965, 8, 368, (uv)
• Wheaton, T.A. et al., Phytochemistry, 1969, 8, 85, (biosynth)
• McLaughlin, J.L. et al., J. Pharm. Sci., 1972, 61, 41; 1973, 62, 408; 411; 1663, (isol, derivs)
• Ranieri, R.L. et al., J.O.C., 1976, 41, 319, (isol, derivs)
• Smith, T.A., Phytochemistry, 1977, 16, 9, (occur)
• Hengstmann, J.H. et al., Arzneim.-Forsch., 1978, 28, 2326, (metab)
• Dattagupta, J.K. et al., Acta Cryst. B, 1982, 38, 2830, (cryst struct)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1283
• Midgley, J.M. et al., J.C.S. Perkin 2, 1989, 963, (cryst struct, abs config)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1250
• Kusu, F. et al., Chem. Pharm. Bull., 1995, 43, 1158, (resoln)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HLV500; SPD000