Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C10H15NO.O4S |
Molecular Weight | 426.527 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | -2 |
SHOW SMILES / InChI
SMILES
[O-]S([O-])(=O)=O.CN(C)CCC1=CC=C(O)C=C1.CN(C)CCC2=CC=C(O)C=C2
InChI
InChIKey=PKCUSEDYJXJFJO-UHFFFAOYSA-L
InChI=1S/2C10H15NO.H2O4S/c2*1-11(2)8-7-9-3-5-10(12)6-4-9;1-5(2,3)4/h2*3-6,12H,7-8H2,1-2H3;(H2,1,2,3,4)/p-2
Hordenine is a natural Phenethylamine compound that occurs in a number of different plants, but especially barley grass. It is structurally similar to the amino acid Tyramine. It antagonized D2-mediated beta-arrestin recruitment indicating functional selectivity. Hordenine inhibited melanogenesis by suppressing cAMP production, which is involved in the expression of melanogenesis-related proteins. Hordenine may be an effective inhibitor of hyperpigmentation. Hordenine is an indirectly acting adrenergic drug. It liberates norepinephrine from stores. In isolated organs and those structures with reduced epinephrine contents, the hordenine-effect is only very poor. Experiments in intact animals (rats, dogs) show that hordenine has a positive inotropic effect upon the heart, increases systolic and diastolic blood pressure, peripheral blood flow volume, inhibits gut movements but has no effect upon the psychomotorical behavior of mice. Hordenine is considered to be generally very safe and well-tolerated in healthy adults. Hordenine is a nootropic compound that works equally well for cognitive enhancement and athletic performance.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2570842 |
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Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28281694 |
13.0 µM [Ki] | ||
Target ID: GO:0006171 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23768344 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Screening and confirmation of drugs in urine: interference of hordenine with the immunoassays and thin layer chromatography methods. | 1992 Apr |
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Characterization of cereal toxicity for celiac disease patients based on protein homology in grains. | 2003 Oct |
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Galanthindole: a new indole alkaloid from Galanthus plicatus ssp. byzantinus. | 2003 Sep |
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Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae). | 2005 Dec |
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Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.). | 2006 Dec 13 |
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Phenylalkylamine alkaloids from Stapelia hirsuta L. | 2006 Jul 10 |
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Chromatographic and electrophoretic methods for the analysis of phenethylamine [corrected] alkaloids in Citrus aurantium. | 2007 Aug 17 |
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Determination of synephrine in bitter orange raw materials, extracts, and dietary supplements by liquid chromatography with ultraviolet detection: single-laboratory validation. | 2007 Jan-Feb |
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Revised NMR data for incartine: an alkaloid from Galanthus elwesii. | 2007 Jul 12 |
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Determination of synephrine in weight-loss products using high performance liquid chromatography with acidic potassium permanganate chemiluminescence detection. | 2007 Jun 12 |
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Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium). | 2007 Nov 28 |
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Biomimetic total synthesis and antimicrobial evaluation of anachelin H. | 2007 Oct 26 |
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Determination of bitter orange alkaloids in dietary supplement Standard Reference Materials by liquid chromatography with atmospheric-pressure ionization mass spectrometry. | 2007 Sep |
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Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in Citrus natural products on a pentafluorophenylpropyl stationary phase. | 2007 Sep 21 |
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The acute effects of the thermogenic supplement Meltdown on energy expenditure, fat oxidation, and hemodynamic responses in young, healthy males. | 2008 Dec 16 |
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Certification of standard reference materials containing bitter orange. | 2008 Jul |
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Examination of a pre-exercise, high energy supplement on exercise performance. | 2009 Jan 6 |
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Thermogenic effect of an acute ingestion of a weight loss supplement. | 2009 Jan 6 |
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Antimicrobial evaluation of clerodane diterpenes from Polyalthia longifolia var. pendula. | 2009 Mar |
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Anticancer drugs from marine flora: an overview. | 2010 |
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Alkaloids in marine algae. | 2010 Feb 4 |
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Role of Mitochondrial Enzymes and Sarcoplasmic ATPase in Cardioprotection Mediated by Aqueous Extract of Desmodium gangeticum (L) DC Root on Ischemic Reperfusion Injury. | 2010 Nov |
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[Alkaloids from Senecio scandens]. | 2010 Oct |
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Changes in apolar metabolites during in vitro organogenesis of Pancratium maritimum. | 2010 Oct-Nov |
Sample Use Guides
In Vivo Use Guide
Sources: https://nootriment.com/hordenine-review/
30 mg taken two or three times a day. The best time to take this is about 30 minutes before exercise.
Route of Administration:
Rectal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2570842
Hordenine at concentrations up to 150 uM produced no measurable contraction but it did affect responses to both noradrenaline and tyramine. 25 uM hordenine potentiated significantly, the tonic responses to submaximal doses of noradrenaline and inhibited those to tyramine.
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ACTIVE MOIETY
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