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

• ChemBase ID: 72987
• Molecular Formular: C9H13NO2
• Molecular Mass: 167.20502
• Monoisotopic Mass: 167.09462866
• SMILES: c1c(ccc(c1)C(O)CNC)O
• Canonical SMILES: CNCC(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-[1-hydroxy-2-(methylamino)ethyl]phenol
• IUPAC Traditional name: synephrine
• Synonyms: Oxedrine; p-Synephrine; Sympatol; Parasympatol; Sympaethamine; Synephrine; 4-Hydroxy-α-[(methylamino)methyl]benzenemethanol; Analeptin; Ethaphene; Simpalon; Synephrin; Synthenate; rac-Synephrine; 1-(4-Hydroxyphenyl)-2-methylaminoethanol; 4-Hydroxy-α-(methylaminomethyl)benzyl alcohol; (±)-Synephrine

Database IDs

• CAS Number: 94-07-5
• EC Number: 202-300-9
• MDL Number: MFCD00002370
• PubChem SID: 24278691; 162037907
• PubChem CID: 7172

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

Physical Property

• Solubility: DMSO
• Apperance: Off-White to Beige Powder
• Melting Point: 184-185°C; 187 °C (dec.)(lit.)

Safety Information

• Storage Condition: -20°C; Hygroscopic, -20°C Freezer, Under inert atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), ADRA2A(150), ADRA2B(151), ADRA2C(152)

Product Information

• Purity: ≥98%
• Salt Data: Free Base
• Linear Formula: HOC6H4CH(CH2NHCH3)OH

DETAILS

Selleck Chemicals - S2362

Research Area: Oxedrine, p-Synephrine, Sympatol, Parasympatol, Sympaethamine
Biological Activity:
Synephrine (Oxedrine) is a compound commonly used for weight loss. Synephrine has gained significant popularity as an alternative to ephedrine. Products containing bitter orange or synephrine are suspected of causing adverse cardiovascular reactions. Synephrine (Oxedrine) is derived primarily from the fruit of Citrus aurantium, a relatively small citrus tree, of which several of its more common names include Bitter Orange, Sour Orange, and Zhi shi. [1]

Sigma Aldrich - S0752

Biochem/physiol Actions
α-adrenoceptor agonist, vasoconstrictor.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S0752.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - S920000

A α-adrenergic receptor agonist, vasoconstrictor.

REFERENCES

• http://en.wikipedia.org/wiki/Synephrine