4-[2-(dimethylamino)ethyl]phenol

• ChemBase ID: 73009
• Molecular Formular: C10H15NO
• Molecular Mass: 165.2322
• Monoisotopic Mass: 165.11536411
• SMILES: c1c(ccc(c1)CCN(C)C)O
• Canonical SMILES: CN(CCc1ccc(cc1)O)C
• InChI: InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3
• InChIKey: KUBCEEMXQZUPDQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(dimethylamino)ethyl]phenol
• IUPAC Traditional name: hordenine
• Synonyms: N; N-dimethyl-4-hydroxyphenylethylamine; Hordenine; 2-(4-Hydroxyphenyl)-N,N-dimethylethylamine; 4-(2-Dimethylaminoethyl)phenol; N,N-Dimethyltyramine; p-Hydroxy-N,N-dimethylphenethylamine; Cactine; Eremursin; Peyocactine; Hordenine; N,N-Dimethyltyramine; Peyocactin; Anhaline; Eremursine; p-[2-(Dimethylamino)ethyl]phenol; Anhalin; Hordenin; N,N-Dimethyl-4-hydroxy-β-phenethylamine; N,N-Dimethyl-p-hydroxyphenethylamine; Ordenina

Database IDs

• CAS Number: 3595-05-9; 539-15-1
• EC Number: 208-710-4
• MDL Number: MFCD00051462
• Beilstein Number: 2207615
• PubChem SID: 162037929
• PubChem CID: 68313
• CHEBI ID: 5764
• CHEMBL: 505789
• Chemspider ID: 61609
• KEGG ID: C06199
• Wikipedia Title: Hordenine

CALCULATED PROPERTIES

• Acid pKa: 10.308364
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.4050452
• LogD (pH = 7.4): 0.058829598
• Log P: 1.6291746
• Molar Refractivity: 51.3366 cm^3
• Polarizability: 19.761398 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; high in: ethanol; ether; chloroform; Methanol
• Apperance: colorless solid; Pale Yellow Solid
• Melting Point: 114-116°C; 116-117°C
• Boiling Point: 173°C at 11 mm Hg; sublimes at 140-150°C

Safety Information

• Storage Condition: -20°C; Refrigerator
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317-H319
• GHS Precautionary statements: P280-P305 + P351 + P338

Product Information

• Purity: ≥97.0% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C10H15NO

DETAILS

Selleck Chemicals - S2385

Research Area: Cancer
Biological Activity:
Hordenine (N,N-dimethyl-4-hydroxyphenylethylamine) is a phenylethylamine alkaloid with antibacterial and antibiotic properties. It stimulates the release of norepinephrine in mammals, working as a stimulant. It is produced in nature by several varieties of plants in the family Cactaceae and by some in Acacia. [1]

Sigma Aldrich - 04476

Biochem/physiol Actions
Hordenine is an alkaloid found in plants, e.g. the roots of germinating barley1,2 and marine algae3. It is a metabolite in tyrosine metabolism, biosynthesized from tyramine by two subsequent N-methylations4, it is metabolized by monoamine oxidase5. Hordenine is a sympathomimetic and its pharmacological actions are of interest, as it is occasionally found in post race urine samples6.

Toronto Research Chemicals - H669600

A phenethylamine alkaloid with antibacterial and antibiotic properties found mainly in plants from the cactaceae family. It showed effects similar to Cytosine (C998950) and acted as a depressant on the central nervous system (CNS) during animal testing.

REFERENCES

• http://en.wikipedia.org/wiki/Hordenine
• Aliev, K.U. et al.: Med. Zhur. Uzbek., 8, 71 (1966)
• Ghosal, S. et al. Planta Medica, 22, 434 (1966)
• Starha, R. et al.: Biochem. Sys. Ecol., 27, 839 (1966)