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04476

Sigma-Aldrich

Hordenine

≥97.0% (HPLC)

Synonyme(s) :

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

Formule empirique (notation de Hill):
C10H15NO
Numéro CAS:
539-15-1
Poids moléculaire :
165.23
Numéro Beilstein :
2207615
Numéro CE :
208-710-4
Numéro MDL:
MFCD00051462
Code UNSPSC :
41116107
ID de substance PubChem :
329747931
Nomenclature NACRES :
NA.25

Niveau de qualité

100

Pureté

≥97.0% (HPLC)

Forme

powder or crystals

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Chaîne SMILES 

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

Clé InChI

KUBCEEMXQZUPDQ-UHFFFAOYSA-N

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Catégories apparentées

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.

Actions biochimiques/physiologiques

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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)
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