Hordes

Structural formula
General
Surname	Hordes
other names	N , N -dimethyltyramine; Anhalonin; Peyocactin; HORD;
Molecular formula	C 10 H 15 NO
Brief description	white to light yellow powder with bulbs
External identifiers / databases
EC number	208-710-4
ECHA InfoCard	100.007.920
PubChem	68313
Wikidata	Q119915
properties
Molar mass	165.23 g · mol -1
Physical state	firmly
Melting point	117.5 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-317-319
	P: 280-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hordenine is a chemical compound found in many plants. Hordenine is one of the alkaloids . It arises biochemically from tyramine .

Hordenin was discovered in 1894 in the cactus Anhalonium fissuratum by Arthur Heffter and named by him anhalonin . In 1906 Leger demonstrated its occurrence in barley ( Hordeum vulgare ), which gave the substance its name, and was able to determine its structure.

pharmacology

Hordenine is a sympathomimetic and activates nicotinic acetylcholine receptors and adrenoceptors in high intravenous doses . This effect does not occur with oral intake (via the digestive tract). Because it is also found in small amounts in forage crops such as barley , animals inadvertently ingest hordes. In horse races, doping can therefore be suspected.

In addition, hordenine has an inhibitory effect on the growth of other plants. Therefore, it is believed that this substance is used for the self-defense of the producing plant.

Analytics

The reliable qualitative and quantitative determination of hordenine is possible after adequate sample preparation by using HPLC .

Cultural meaning

Of the 13,000 different food ingredients that were investigated by a research group at the University of Erlangen-Nürnberg, the beer ingredient hordenine has the best activity against the dopamine D2 receptor.

literature

Mann JD, Steinhart CE, Mudd SH: Alkaloids and Plant Metabolism. V. The Distribution And Formation Of Tyramine Methylpherase During Germination Of Barley . In: J Biol Chem . 238, No. 2, February 1963, pp. 676-681.
Sommer, Thomas; Huebner, Harald; El Kerdawy, Ahmed; Gmeiner, Peter; Pischetsrieder, Monika ; Clark, Tim: Identification of the Beer Component Hordenine as Food-Derived Dopamine D2 Receptor Agonist by Virtual Screening a 3D Compound Database. Scientific Reports (2017), 7: 44201, doi : 10.1038 / srep44201 .

Individual evidence

↑ ^a ^b ^c ^d Hordenine data sheet at Sigma-Aldrich , accessed on April 4, 2011 ( PDF ).

↑ Arthur Heffter: About two Cacteenalkaloids . In: Reports of the German Chemical Society . Volume 27, number 3, pp. 2975-2979, doi : 10.1002 / cber.18940270362 .

↑ Güven KC, Percot A, Sezik E: Alkaloids in marine algae . In: Mar Drugs . 8, No. 2, 2010, pp. 269-284. doi : 10.3390 / md8020269 . PMID 20390105 . PMC 2852838 (free full text).

↑ Hapke HJ, Strathmann W: [Pharmacological effects of hordenine] . In: DTW. German Veterinarian Weekly . 102, No. 6, June 1995, pp. 228-232. PMID 8582256 .

↑ Frank M, Weckman TJ, Wood T, et al. : Hordenine: pharmacology, pharmacokinetics and behavioral effects in the horse . In: Equine Vet J.. . 22, No. 6, November 1990, pp. 437-441. PMID 2269269 .

^ Richard A. Sams: Review of Possible Sources of Exposure of Horses to Natural Products and Environmental Contaminants Resulting in Regulatory Action . (PDF) In: Proceedings of the Annual Convention of the AAEP . 43, 1997, pp. 220-223. Retrieved August 11, 2010.

^ Lovett JV: Changing perceptions of allelopathy and biological control . In: Biol Agric Hortic . 8, No. 2, 1991, pp. 89-100.

^ Lovett JV, Hoult AHC: Biological activity of barley secondary metabolites . In: Proceedings of the 7th Australian Agronomy Conference . 1993.

^ Hoult AH, Lovett JV: Biologically active secondary metabolites of barley. III. A method for identification and quantification of hordenine and gramine in barley by high-performance liquid chromatography. , J Chem Ecol. 1993 Oct; 19 (10): 2245-54, PMID 24248573

↑ https://www.fau.de/2017/09/news/wissenschaft/bier-macht-gluecklich/

[Sigma-1] Hordenine data sheet at Sigma-Aldrich , accessed on April 4, 2011 ( PDF ).

[2] Arthur Heffter: About two Cacteenalkaloids . In: Reports of the German Chemical Society . Volume 27, number 3, pp. 2975-2979, doi : 10.1002 / cber.18940270362 .

[3] Güven KC, Percot A, Sezik E: Alkaloids in marine algae . In: Mar Drugs . 8, No. 2, 2010, pp. 269-284. doi : 10.3390 / md8020269 . PMID 20390105 . PMC 2852838 (free full text).

[4] Hapke HJ, Strathmann W: [Pharmacological effects of hordenine] . In: DTW. German Veterinarian Weekly . 102, No. 6, June 1995, pp. 228-232. PMID 8582256 .

[5] Frank M, Weckman TJ, Wood T, et al. : Hordenine: pharmacology, pharmacokinetics and behavioral effects in the horse . In: Equine Vet J.. . 22, No. 6, November 1990, pp. 437-441. PMID 2269269 .

[6] Richard A. Sams: Review of Possible Sources of Exposure of Horses to Natural Products and Environmental Contaminants Resulting in Regulatory Action . (PDF) In: Proceedings of the Annual Convention of the AAEP . 43, 1997, pp. 220-223. Retrieved August 11, 2010.

[7] Lovett JV: Changing perceptions of allelopathy and biological control . In: Biol Agric Hortic . 8, No. 2, 1991, pp. 89-100.

[8] Lovett JV, Hoult AHC: Biological activity of barley secondary metabolites . In: Proceedings of the 7th Australian Agronomy Conference . 1993.

[9] Hoult AH, Lovett JV: Biologically active secondary metabolites of barley. III. A method for identification and quantification of hordenine and gramine in barley by high-performance liquid chromatography. , J Chem Ecol. 1993 Oct; 19 (10): 2245-54, PMID 24248573

[10] ttps://www.fau.de/2017/09/news/wissenschaft/bier-macht-gluecklich/