4-(2-Dimethylaminoethyl)phenol
Hordeine · Hordenin · Anhalin · Cactine · Anhaline · Hordetin · Ordenina · Ordenine
Identifikatoren & physikalische Daten
| CAS No. | 539-15-1 |
|---|---|
| Summenformel | C10H15NO |
| Durchschnittliche Molmasse | 165,23 g/mol |
| Monoisotopische Masse | 165,1153641 g/mol |
| SMILES | CN(C)CCc1ccc(O)cc1 |
| InChIKey | KUBCEEMXQZUPDQ-UHFFFAOYSA-N |
| PubChem CID | 68313 |
| ChEMBL | CHEMBL505789 |
| ChEBI | CHEBI:5764 |
| EC No. | 208-710-4 |
| DTXSID | DTXSID2046096 |
| Lokaler Name | 4-(2-Dimethylaminoethyl)phenol |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 23,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 117 |
| Arzneimittel | Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds |
| Löslichkeit | 7 mg/mLDMSO (Slightly), Methanol (Slightly) |
| Human Drugs | Pharmaceuticals |
| Schmelzpunkt | 117.5 °C117-118° |
| Physical Description | Solid |
| Collision Cross Section | 137.8 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| Siedepunkt | bp11 173° |
| Dichte | 1.0203 (rough estimate) |
| Brechungsindex | 1.4820 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 10.05±0.26(Predicted) |
| Farbe | Pale Yellow to Dark Beige |
| Merck | 14,4746 |
| BRN | 2207615 |
| Hauptanwendungen | metabolomicsvitamins, nutraceuticals, and natural products |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN PROTECTING |
| 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 |
| SMILES | CN(C)CCc1ccc(O)cc1 || CN(C)CCc1ccc(O)cc1 |
| LogP (Verteilungskoeffizient) | 1.400 (est) |
| CAS Datenbank | 539-15-1(CAS DataBase Reference) |
| NIST chemische Informationen | Phenol, 4-[2-(dimethylamino)ethyl]-(539-15-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (92.7%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (92.7%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29222990 |
| R-Sätze (R) | 22-36-43 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36/37 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
Hordenine (Item No. 21626) is a naturally occurring alkaloid found in a variety of plants, most commonly germinated barley (Hordeum species) from which the name is derived, and is structurally classified as a phenethylamine. It is biosynthesized by the step-wise double methylation of tyramine . Hordenine binds to and activates the dopamine D2 receptor (Ki = 13 μM) but antagonizes D2 receptor β-arrestin recruitment. It inhibits tyrosinase activity and expression at concentrations ≥ 50 μM resulting in reduced melanin accumulation in human melanocytes. Hordenine is present in significant amounts in beer and can be measured in serum in the free form, for up to 2 hours, and the glucuronidated form, for up to 6 hours, after beer consumption. This product is intended for research and forensic applications.
Verwenden
Hordenine is suitable to study the effect of reed canary grass alkoloids on in vito digestibility. It is also suitable for use as a standard to identify endogenous hordenine in ungerminated and germinated barley by HPLC/diode array detection analysis. Hordenine may be used as an analytical reference material and in research on the activities of phenethylamine type alkaloids.