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Merck

04476

Sigma-Aldrich

Hordenine

≥97.0% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C10H15NO
Número de CAS:
Peso molecular:
165.23
Beilstein/REAXYS Number:
2207615
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.25

Quality Level

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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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

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


Certificados de análisis (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)
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)
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
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

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