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04476

Sigma-Aldrich

Hordenin

≥97.0% (HPLC)

Synonym(e):

4-(2-Dimethylaminoethyl)-phenol, N,N-Dimethyl-tyramin, p-Hydroxy-N,N-dimethyl-phenethylamin, Anhalin, Cactin, Eremursine, Peyocactin

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About This Item

Empirische Formel (Hill-System):
C10H15NO
CAS-Nummer:
539-15-1
Molekulargewicht:
165.23
Beilstein:
2207615
EG-Nummer:
208-710-4
MDL-Nummer:
MFCD00051462
UNSPSC-Code:
41116107
PubChem Substanz-ID:
329747931
NACRES:
NA.25

Assay

≥97.0% (HPLC)

Form

powder or crystals

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES String

CN(C)CCc1ccc(O)cc1

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

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Anwendung

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.

Biochem./physiol. Wirkung

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.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Hordenine content of the marine alga Mastocarpus stellatus and the algal food product carrageen.
Barwell, C.J., et al.
Phytotherapy Research, 3, 67-69 (1989)
C A Bourke et al.
Australian veterinary journal, 65(7), 218-220 (1988-07-01)
The acute toxicity for sheep of 3 alkaloids that occur in Phalaris acquatica was examined by intravenous and oral administration. The lowest tested dose rates that produced clinically observed signs were, for 5-methoxy dimethyltryptamine, 0.1 mg/kg body weight intravenously and
C J Barwell et al.
The Journal of pharmacy and pharmacology, 41(6), 421-423 (1989-06-01)
The selectivity of the naturally occurring amine, N,N-dimethyltyramine (hordenine) for monoamine oxidase (MAO) and its action upon isolated vasa deferentia of the rat was investigated. Hordenine was deaminated by rat liver MAO with a Michaelis constant of 479 microM and
Studies on the mechanism of action of monoamine oxidase: metabolism of N,N-dimethyltryptamine and N,N-dimethyltryptamine-N-oxide.
T E SMITH et al.
Biochemistry, 1, 137-143 (1962-01-01)
A K Singh et al.
Forensic science international, 54(1), 9-22 (1992-04-01)
Hordenine cross-reacted with various enzyme linked immunosorbent assay (ELISA) or radioimmunoassay (RIA) kits used for the screening of urine samples. Morphine-ELISA kit was most sensitive, whereas etorphine- and buprenorphine-ELISA kits were least sensitive to hordenine cross-reactivity. Hordenine also interfered with
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