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Details

Stereochemistry ACHIRAL
Molecular Formula C10H15NO.ClH
Molecular Weight 201.693
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HORDENINE HYDROCHLORIDE

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
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
Screening and confirmation of drugs in urine: interference of hordenine with the immunoassays and thin layer chromatography methods.
1992 Apr
Galanthindole: a new indole alkaloid from Galanthus plicatus ssp. byzantinus.
2003 Sep
Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.).
2006 Dec 13
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
The acute effects of the thermogenic supplement Meltdown on energy expenditure, fat oxidation, and hemodynamic responses in young, healthy males.
2008 Dec 16
Certification of standard reference materials containing bitter orange.
2008 Jul
Examination of a pre-exercise, high energy supplement on exercise performance.
2009 Jan 6
Thermogenic effect of an acute ingestion of a weight loss supplement.
2009 Jan 6
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
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 04:02:27 GMT 2023
Edited
by admin
on Sat Dec 16 04:02:27 GMT 2023
Record UNII
575FR6P9I9
Record Status Validated (UNII)
Record Version
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Name Type Language
HORDENINE HYDROCHLORIDE
MI  
Common Name English
ANHALINE HYDROCHLORIDE
Common Name English
HORDENINE HYDROCHLORIDE [MI]
Common Name English
NSC-172175
Code English
PHENOL, 4-(2-(DIMETHYLAMINO)ETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
PHENOL, 4-(2-(DIMETHYLAMINO)ETHYL)-, HYDROCHLORIDE
Systematic Name English
N,N-DIMETHYLTYRAMINE HYDROCHLORIDE
Systematic Name English
PHENOL, P-(2-(DIMETHYLAMINO)ETHYL)-, HYDROCHLORIDE
Common Name English
Code System Code Type Description
MERCK INDEX
m6055
Created by admin on Sat Dec 16 04:02:27 GMT 2023 , Edited by admin on Sat Dec 16 04:02:27 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID70209023
Created by admin on Sat Dec 16 04:02:27 GMT 2023 , Edited by admin on Sat Dec 16 04:02:27 GMT 2023
PRIMARY
PUBCHEM
165396
Created by admin on Sat Dec 16 04:02:27 GMT 2023 , Edited by admin on Sat Dec 16 04:02:27 GMT 2023
PRIMARY
CAS
6027-23-2
Created by admin on Sat Dec 16 04:02:27 GMT 2023 , Edited by admin on Sat Dec 16 04:02:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-892-6
Created by admin on Sat Dec 16 04:02:27 GMT 2023 , Edited by admin on Sat Dec 16 04:02:27 GMT 2023
PRIMARY
NSC
172175
Created by admin on Sat Dec 16 04:02:27 GMT 2023 , Edited by admin on Sat Dec 16 04:02:27 GMT 2023
PRIMARY
FDA UNII
575FR6P9I9
Created by admin on Sat Dec 16 04:02:27 GMT 2023 , Edited by admin on Sat Dec 16 04:02:27 GMT 2023
PRIMARY
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