Hordenine Chemical Properties

Melting point:

117-118°

Boiling point:

bp11 173°

Density 

1.0203 (rough estimate)

refractive index 

1.4820 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

10.05±0.26(Predicted)

form 

Solid

color 

Pale Yellow to Dark Beige

Merck 

14,4746

BRN 

2207615

LogP

1.400 (est)

CAS DataBase Reference

539-15-1(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 4-[2-(dimethylamino)ethyl]-(539-15-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43

Safety Statements 

26-36/37

WGK Germany 

3

HS Code 

29222990

Hordenine Usage And Synthesis

Description

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 (K_i = 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.

Chemical Properties

Light yellow solid

Uses

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.

Uses

A 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.

Definition

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

Biochem/physiol Actions

Hordenine is an alkaloid found in plants, e.g. the roots of germinating barley and marine algae. It is a metabolite in tyrosine metabolism, biosynthesized from tyramine by two subsequent N-methylations, it is metabolized by monoamine oxidase. Hordenine is a sympathomimetic and its pharmacological actions are of interest, as it is occasionally found in post race urine samples. Hordenine inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production. cAMP is involved in the expression of melanogenesis-related proteins. Hordenine may be used in the inhibition of hyperpigmentation. It is present in barley roots from the first day of seed germination, but is not present in seeds.

Purification Methods

Crystallise Hordenine from EtOH or H2O and sublime it at 105o/5mm. The 4,4’-dichlorodiphenyl disulfimide salt has m 145-146o (from Me2CO/H2O) [Runge et al. Chem Ber 88 50 1955]. [Beilstein 13 H 626, 13 I 236, 13 II 356, 13 III 1640, 13 IV 1790.]

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