U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

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
Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae).
2005 Dec
Determination of synephrine in bitter orange raw materials, extracts, and dietary supplements by liquid chromatography with ultraviolet detection: single-laboratory validation.
2007 Jan-Feb
Revised NMR data for incartine: an alkaloid from Galanthus elwesii.
2007 Jul 12
Determination of synephrine in weight-loss products using high performance liquid chromatography with acidic potassium permanganate chemiluminescence detection.
2007 Jun 12
Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium).
2007 Nov 28
Biomimetic total synthesis and antimicrobial evaluation of anachelin H.
2007 Oct 26
Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in Citrus natural products on a pentafluorophenylpropyl stationary phase.
2007 Sep 21
Certification of standard reference materials containing bitter orange.
2008 Jul
Antimicrobial evaluation of clerodane diterpenes from Polyalthia longifolia var. pendula.
2009 Mar
Anticancer drugs from marine flora: an overview.
2010
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
[Alkaloids from Senecio scandens].
2010 Oct
Changes in apolar metabolites during in vitro organogenesis of Pancratium maritimum.
2010 Oct-Nov
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 Fri Dec 15 18:36:25 GMT 2023
Edited
by admin
on Fri Dec 15 18:36:25 GMT 2023
Record UNII
O6NSW8P8Y8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HORDENINE SULFATE
WHO-DD  
Common Name English
HORDENINE SULPHATE
Common Name English
PEYOCACTINE SULFATE
Common Name English
Hordenine sulfate [WHO-DD]
Common Name English
NSC-148336
Code 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 Fri Dec 15 18:36:25 GMT 2023 , Edited by admin on Fri Dec 15 18:36:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID201017262
Created by admin on Fri Dec 15 18:36:25 GMT 2023 , Edited by admin on Fri Dec 15 18:36:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
210-749-7
Created by admin on Fri Dec 15 18:36:25 GMT 2023 , Edited by admin on Fri Dec 15 18:36:25 GMT 2023
PRIMARY
NSC
148336
Created by admin on Fri Dec 15 18:36:25 GMT 2023 , Edited by admin on Fri Dec 15 18:36:25 GMT 2023
PRIMARY
PUBCHEM
76972130
Created by admin on Fri Dec 15 18:36:25 GMT 2023 , Edited by admin on Fri Dec 15 18:36:25 GMT 2023
PRIMARY
EVMPD
SUB14118MIG
Created by admin on Fri Dec 15 18:36:25 GMT 2023 , Edited by admin on Fri Dec 15 18:36:25 GMT 2023
PRIMARY
RXCUI
236237
Created by admin on Fri Dec 15 18:36:25 GMT 2023 , Edited by admin on Fri Dec 15 18:36:25 GMT 2023
PRIMARY RxNorm
CAS
622-64-0
Created by admin on Fri Dec 15 18:36:25 GMT 2023 , Edited by admin on Fri Dec 15 18:36:25 GMT 2023
PRIMARY
SMS_ID
100000077591
Created by admin on Fri Dec 15 18:36:25 GMT 2023 , Edited by admin on Fri Dec 15 18:36:25 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY