4-(2-Dimethylaminoethyl)phenol

Hordenine

HCID 68313CAS 539-15-1

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Grundinformationen

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 Å²
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 Å² [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)
Aggregatzustand: Solid
pka: 10.05 · 10.05±0.26(Predicted)
Farbe: Pale Yellow to Dark Beige
Merck: 14 · 14,4746
BRN: 2207615 · 2207615
Major Application: 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: 1.4 · 1.400 (est)
CAS Datenbank: 539 · 539-15-1(CAS DataBase Reference)
NIST chemische Informationen: 4 · Phenol, 4-[2-(dimethylamino)ethyl]-(539-15-1)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 2 Einträge

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.