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Details

Stereochemistry ACHIRAL
Molecular Formula C10H15NO
Molecular Weight 165.2322
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HORDENINE

SMILES

CN(C)CCC1=CC=C(O)C=C1

InChI

InChIKey=KUBCEEMXQZUPDQ-UHFFFAOYSA-N
InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3

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

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
Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.).
2006 Dec 13
Revised NMR data for incartine: an alkaloid from Galanthus elwesii.
2007 Jul 12
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
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 Sat Dec 16 03:24:15 UTC 2023
Edited
by admin
on Sat Dec 16 03:24:15 UTC 2023
Record UNII
K3489CA082
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HORDENINE
INCI   MI   WHO-DD  
INCI  
Official Name English
P-(2-(DIMETHYLAMINO)ETHYL)PHENOL
Common Name English
P-HYDROXY-N,N-DIMETHYLPHENETHYLAMINE
Common Name English
PHENOL, P-(2-(DIMETHYLAMINO)ETHYL)-
Common Name English
4-(2-DIMETHYLAMINOETHYL)PHENOL
Systematic Name English
N,N-DIMETHYLTYRAMINE
Systematic Name English
ANHALIN
Brand Name English
CACTINE
Brand Name English
N,N-DIMETHYL-P-HYDROXYPHENETHYLAMINE
Common Name English
HORDENINE [INCI]
Common Name English
Hordenine [WHO-DD]
Common Name English
HORDENINE [MI]
Common Name English
ORDENINA
Brand Name English
PEYOCACTINE
Brand Name English
HORDENIN
Common Name English
ANHALINE
Brand Name English
N,N-DIMETHYL-4-HYDROXY-.BETA.-PHENETHYLAMINE
Systematic Name English
EREMURSINE
Brand Name English
Classification Tree Code System Code
DSLD 1786 (Number of products:143)
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
DSLD 1118 (Number of products:214)
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
Code System Code Type Description
CAS
539-15-1
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY
SMS_ID
300000033935
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID2046096
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY
RXCUI
27120
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY RxNorm
PUBCHEM
68313
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY
FDA UNII
K3489CA082
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY
MESH
C007964
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY
CHEBI
5764
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY
MERCK INDEX
m6055
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
208-710-4
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY
WIKIPEDIA
HORDENINE
Created by admin on Sat Dec 16 03:24:16 UTC 2023 , Edited by admin on Sat Dec 16 03:24:16 UTC 2023
PRIMARY
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