Hordenine (HCID 68313)

Overview

Hordenine is a phenethylamine alkaloid. It has a role as a mouse metabolite and a human metabolite.

Names & identifiers

Preferred name: Hordenine
IUPAC: 4-[2-(dimethylamino)ethyl]phenol
English name: Hordenine
Molecular formula: C10H15NO
Molecular weight: 165.23

Names & synonyms

Hordenine539-15-14-[2-(Dimethylamino)ethyl]phenol4-(2-(Dimethylamino)ethyl)phenolAnhalineN,N-Dimethyltyramine4-(2-Dimethylaminoethyl)phenolPeyocactineAnhalinCactineEremursineOrdenina

Show more names

HordeineHordeninHordetinOrdenineEremursin

p-(2-Dimethylaminoethyl)phenolDTXSID2046096K3489CA082CHEBI:5764DTXCID0026096N,N-Dimethyl-4-hydroxy-beta-phenethylamineRefChem:38568208-710-4

Database identifiers

CAS: 539-15-1
PubChem CID: 68313
DTXSID: DTXSID2046096
ChEMBL: CHEMBL505789
ChEBI: CHEBI:5764
UNII: K3489CA082
EC Number: 208-710-4
Nikkaji: J6.381I

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 23.5 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 12
Formal charge: 0
Complexity: 117

Experimental & physicochemical properties

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)]

Physicochemical properties

Melting point: 117 · 117-118°
Boiling point: 11 · bp11 173°
Density: 1.0203 · 1.0203 (rough estimate)
refractive index: 1.482 · 1.4820 (estimate)
storage temp.: Inert atmosphere,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 10.05 · 10.05±0.26(Predicted)
color: Pale Yellow to Dark Beige
Merck: 14 · 14,4746
BRN: 2207615 · 2207615
Major Application: metabolomicsvitamins, nutraceuticals, and natural products
Cosmetics Ingredients Functions: 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 DataBase Reference: 539 · 539-15-1(CAS DataBase Reference)
FDA UNII: 3489 CA082 · K3489CA082
NIST Chemistry Reference: 4 · Phenol, 4-[2-(dimethylamino)ethyl]-(539-15-1)
UNSPSC Code: 41116107 · 41116107
NACRES: 25 · NA.25
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xn
Risk Statements: 22 · 22-36-43
Safety Statements: 26 · 26-36/37
WGK Germany: 3 · 3
HS Code: 29222990 · 29222990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (92.7%)

Safety data

wgk: 3
hs_code: 29222990
risk_code: 22-36-43
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26-36/37
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Uses & manufacturing

Use ClassificationPharmaceuticals

Applications · 3 items

DescriptionHordenine (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.

UsesHordenine 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.

UsesA 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.