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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
Structure of HORDENINE SULFATE

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

HIDE SMILES / InChI

Molecular Formula C10H15NO
Molecular Weight 165.2322
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
13.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Role of Mitochondrial Enzymes and Sarcoplasmic ATPase in Cardioprotection Mediated by Aqueous Extract of Desmodium gangeticum (L) DC Root on Ischemic Reperfusion Injury.
2010-11
[Alkaloids from Senecio scandens].
2010-10
Alkaloids in marine algae.
2010-02-04
Anticancer drugs from marine flora: an overview.
2010
Changes in apolar metabolites during in vitro organogenesis of Pancratium maritimum.
2009-11-17
Antimicrobial evaluation of clerodane diterpenes from Polyalthia longifolia var. pendula.
2009-03
Examination of a pre-exercise, high energy supplement on exercise performance.
2009-01-06
Thermogenic effect of an acute ingestion of a weight loss supplement.
2009-01-06
The acute effects of the thermogenic supplement Meltdown on energy expenditure, fat oxidation, and hemodynamic responses in young, healthy males.
2008-12-16
Certification of standard reference materials containing bitter orange.
2008-07
Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium).
2007-11-28
Biomimetic total synthesis and antimicrobial evaluation of anachelin H.
2007-10-26
Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in Citrus natural products on a pentafluorophenylpropyl stationary phase.
2007-09-21
Determination of bitter orange alkaloids in dietary supplement Standard Reference Materials by liquid chromatography with atmospheric-pressure ionization mass spectrometry.
2007-09
Chromatographic and electrophoretic methods for the analysis of phenethylamine [corrected] alkaloids in Citrus aurantium.
2007-08-17
Revised NMR data for incartine: an alkaloid from Galanthus elwesii.
2007-07-12
Determination of synephrine in weight-loss products using high performance liquid chromatography with acidic potassium permanganate chemiluminescence detection.
2007-06-12
Determination of synephrine in bitter orange raw materials, extracts, and dietary supplements by liquid chromatography with ultraviolet detection: single-laboratory validation.
2007-03-22
Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.).
2006-12-13
Phenylalkylamine alkaloids from Stapelia hirsuta L.
2006-07-10
Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae).
2005-12
Characterization of cereal toxicity for celiac disease patients based on protein homology in grains.
2003-10
Galanthindole: a new indole alkaloid from Galanthus plicatus ssp. byzantinus.
2003-09
Screening and confirmation of drugs in urine: interference of hordenine with the immunoassays and thin layer chromatography methods.
1992-04
Patents

Sample Use Guides

In Vivo Use Guide
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
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:16:39 GMT 2025
Edited
by admin
on Mon Mar 31 19:16:39 GMT 2025
Record UNII
O6NSW8P8Y8
Record Status Validated (UNII)
Record Version
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Name Type Language
HORDENINE SULFATE
WHO-DD  
Common Name English
NSC-148336
Preferred Name English
HORDENINE SULPHATE
Common Name English
PEYOCACTINE SULFATE
Common Name English
Hordenine sulfate [WHO-DD]
Common Name English
PHENOL, P-(2-(DIMETHYLAMINO)ETHYL)-, SULFATE (2:1) (SALT)
Common Name English
P-HYDROXY-N,N-DIMETHYLPHENETHYLAMINE SULFATE
Common Name English
ANHALINE SULFATE
Common Name English
Code System Code Type Description
FDA UNII
O6NSW8P8Y8
Created by admin on Mon Mar 31 19:16:39 GMT 2025 , Edited by admin on Mon Mar 31 19:16:39 GMT 2025
PRIMARY
EPA CompTox
DTXSID201017262
Created by admin on Mon Mar 31 19:16:39 GMT 2025 , Edited by admin on Mon Mar 31 19:16:39 GMT 2025
PRIMARY
ECHA (EC/EINECS)
210-749-7
Created by admin on Mon Mar 31 19:16:39 GMT 2025 , Edited by admin on Mon Mar 31 19:16:39 GMT 2025
PRIMARY
NSC
148336
Created by admin on Mon Mar 31 19:16:39 GMT 2025 , Edited by admin on Mon Mar 31 19:16:39 GMT 2025
PRIMARY
PUBCHEM
76972130
Created by admin on Mon Mar 31 19:16:39 GMT 2025 , Edited by admin on Mon Mar 31 19:16:39 GMT 2025
PRIMARY
EVMPD
SUB14118MIG
Created by admin on Mon Mar 31 19:16:39 GMT 2025 , Edited by admin on Mon Mar 31 19:16:39 GMT 2025
PRIMARY
RXCUI
236237
Created by admin on Mon Mar 31 19:16:39 GMT 2025 , Edited by admin on Mon Mar 31 19:16:39 GMT 2025
PRIMARY RxNorm
CAS
622-64-0
Created by admin on Mon Mar 31 19:16:39 GMT 2025 , Edited by admin on Mon Mar 31 19:16:39 GMT 2025
PRIMARY
SMS_ID
100000077591
Created by admin on Mon Mar 31 19:16:39 GMT 2025 , Edited by admin on Mon Mar 31 19:16:39 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY