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04476

Sigma-Aldrich

Hordenine

≥97.0% (HPLC)

Synonyma:

2-(4-Hydroxyphenyl)-N,N-dimethylethylamine, 4-(2-Dimethylaminoethyl)phenol, N,N-Dimethyltyramine, p-Hydroxy-N,N-dimethylphenethylamine, Anhaline, Cactine, Eremursin, Peyocactine

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen
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About This Item

Empirický vzorec (Hillův zápis):
C10H15NO
Číslo CAS:
539-15-1
Molekulová hmotnost:
165.23
Beilstein/REAXYS Number:
2207615
EC Number:
208-710-4
MDL number:
MFCD00051462
UNSPSC Code:
41116107
PubChem Substance ID:
329747931
NACRES:
NA.25

Quality Level

100

assay

≥97.0% (HPLC)

form

powder or crystals

application(s)

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

InChI key

KUBCEEMXQZUPDQ-UHFFFAOYSA-N

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Související kategorie

Application

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 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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (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
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)
H J Hapke et al.
DTW. Deutsche tierarztliche Wochenschrift, 102(6), 228-232 (1995-06-01)
Hordenine is an ingredient of some plants which are used as feed for animals, i.e. in sprouting barley. After ingestion of such feed hordenine may be detected in blood or urine of horses which in case of racing horses may
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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