4-(2-Dimethylaminoethyl)phenol
Hordenine
Grundinformationen
- CAS
539-15-1- Standard-SMILES
CN(C)CCc1ccc(O)cc1- InChIKey
KUBCEEMXQZUPDQ-UHFFFAOYSA-N- Summenformel
- C10H15NO
- Durchschnittliche Molmasse
- 165,23 g/mol
- Monoisotopische Masse
- 165,1153641
Überblick
Hordenine is a phenethylamine alkaloid. It has a role as a mouse metabolite and a human metabolite.
Namen und Bezeichner
- Bevorzugter Name
- Hordenine
- IUPAC
- 4-[2-(dimethylamino)ethyl]phenol
- Lokaler Name
- 4-(2-Dimethylaminoethyl)phenol
- Englischer Name
- Hordenine
- Summenformel
- C10H15NO
- Molmasse
- 165.23
Namen und Synonyme
Hordenine539-15-14-[2-(Dimethylamino)ethyl]phenol4-(2-(Dimethylamino)ethyl)phenolAnhalineN,N-Dimethyltyramine4-(2-Dimethylaminoethyl)phenolPeyocactineAnhalinCactineEremursineOrdenina
Weitere Namen anzeigen
HordeineHordeninHordetinOrdenineEremursin
p-(2-Dimethylaminoethyl)phenolDTXSID2046096K3489CA082CHEBI:5764DTXCID0026096N,N-Dimethyl-4-hydroxy-beta-phenethylamineRefChem:38568208-710-4
Datenbank-Bezeichner
- CAS
539-15-1- PubChem CID
- 68313
- DTXSID
DTXSID2046096- ChEMBL
CHEMBL505789- ChEBI
CHEBI:5764- UNII
- K3489CA082
- EC Number
- 208-710-4
- Nikkaji
- J6.381I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,1
- Polarare Oberfläche (TPSA)
- 23,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 117
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Solubility7 mg/mL
Human DrugsPharmaceuticals
Melting Point117.5 °C
Physical DescriptionSolid
Collision Cross Section137.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physikochemische Eigenschaften
- Schmelzpunkt
- 117 · 117-118°
- Siedepunkt
- 11 · bp11 173°
- Dichte
- 1.0203 · 1.0203 (rough estimate)
- Brechungsindex
- 1.482 · 1.4820 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (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.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (92.7%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29222990
- risk_code
- 22-36-43
- hazard_code
- Xn
- safety_code
- 26-36/37
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Verwendung und Herstellung
Use ClassificationPharmaceuticals
Anwendungen
BeschreibungHordenine (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.
VerwendenHordenine 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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Zugehörige Reaktionen
16
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