Hordenine
Basic information
- CAS
539-15-1- Standard SMILES
CN(C)CCc1ccc(O)cc1- InChIKey
KUBCEEMXQZUPDQ-UHFFFAOYSA-N- Molecular formula
- C10H15NO
- Average molar mass
- 165.23 g/mol
- Monoisotopic mass
- 165.1153641
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 Ų
- 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 Ų [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
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
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
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.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Hordenine is a phenethylamine alkaloid. It has a role as a human metabolite and a mouse metabolite.
Related reactions
16 records
Compound notes
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