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Higenamine

$225

  • Brand : BIOFRON

  • Catalogue Number : BF-H4002

  • Specification : 98%(HPLC)

  • CAS number : 5843-65-2

  • Formula : C16H17NO3

  • Molecular Weight : 271.314

  • PUBCHEM ID : 114840

  • Volume : 20mg

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Catalogue Number

BF-H4002

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

271.314

Appearance

White crystalline powder

Botanical Source

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O

Synonyms

Higenamine/1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydroisochinolin-6,7-diol/(R,S)-norcoclaurine/(+-)-O-Demethylcoclaurine/Coclaurine,O-demethyl-,(+-)/1-(p-hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline/6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-/(+-)-Demethylcoclaurine/rac-norcoclaurine/1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydro-6,7-isoquinolinediol/(±)-HIGENAMINE/Norcoclaurine/1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol/1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol/Isoquinolin-6,7-diol, 1,2,3,4-tetrahydro-1-[4-hydroxybenzyl]-/6,7-Isoquinolinediol, 1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-, (±)-/6,7-Isoquinolinediol,1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-,(+-)

IUPAC Name

1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Applications

Density

1.3±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

209.6±20.7 °C

Boiling Point

522.4±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2

InChl Key

WZRCQWQRFZITDX-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:5843-65-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31642280

Abstract

A method combining QuEChERS with liquid chromatography-tandem mass spectrometry (LC-MS/MS) was developed for the determination of higenamine in Chinese herbal medicine, condiments, and topical medicine. The sample was subjected to extraction using a formic acid-ethanol mixture, followed by purification of the QuEChERS sorbents; then, the extraction solution was introduced into the LC-MS/MS system for detection in multiple reaction monitoring (MRM) mode. Under the optimal conditions, the detection limit of the developed method was 0.03 ng/g, and the linear range was 0.10-100 ng/g with a relative standard deviation (RSD) of 4.33% (0.5 ng/g, n=7). The method was then applied to the determination of higenamine in 13 kinds of Chinese herbal medicine, four kinds of condiments, and a topical medicine. Higenamine was detected in dried lotus leaf, dried lotus seed, Chinese yam, Yuzhu, Yam, Sichuan pepper, Cassia, and the topical medicine at 9667.6, 1183.8, 21.5, 8.2, 8.5, 148.6, 21.3, and 173.3 μg/kg, respectively. The recoveries of higenamine in Sichuan pepper and cassia was 92.6%-109.8%. In conclusion, the method is fast, simple, reliable, and suitable for use in batch operation.

KEYWORDS

Chinese herbal medicine; QuEChERS; condiments; higenamine; liquid chromatography-tandem mass spectrometry (LC-MS/MS)

Title

[Determination of higenamine in Chinese herbal medicine, condiments, and topical medicine by QuEChERS combined with liquid chromatography-tandem mass spectrometry].

Author

Wang H1, Tang Y2, Zhao X1, Ye C1, Guo S1, Luo J1, Xiong L1, Cao W1, Wu J1, Wang P1.

Publish date

2019 Oct 8

PMID

31240795

Abstract

RATIONALE:
Retroactive analysis of previously tested urine samples has become an important sports anti-doping tool. Retroactive reprocessing of old data files acquired from a generic screening procedure can reveal detection of initially unknown substances, like illegal drugs and newly identified metabolites.

METHODS:
To be able to efficiently search through hundreds to thousands of liquid chromatography high-resolution full-scan Orbitrap mass spectrometry data files of anti-doping samples, a combination of MetAlign and HR_MS_Search software has been developed. MetAlign reduced the data size ca 100-fold making possible local storage of a massive volume of data.

RESULTS:
The newly developed HR_MS_Search module can search through the reduced data files for new compounds (mass or isotope pattern) defined by mass windows and retention time windows. A search for 33 analytes in 940 reduced data files lasted 10 s. The output of the automatic search was compared to the standard manual routine evaluation. The results of searching were evaluated in terms of false negatives and false positives. The newly banned b2-agonist higenamine and its metabolite coclaurine were successfully searched in reduced data files originating from a testing period for which these substances were not banned, as an example of retroactive analysis.

CONCLUSIONS:
The freeware MetAlign software and its automatic searching module HR_MS_Search facilitated the retroactive reprocessing of reduced full-scan high-resolution liquid chromatography/mass spectrometry screening data files and created a new tool in anti-doping laboratories’ network.

© 2019 John Wiley & Sons, Ltd.

Title

Ultra-fast retroactive processing of liquid chromatography high-resolution full-scan Orbitrap mass spectrometry data in anti-doping screening of human urine.

Author

Lommen A1, Elaradi A2, Vonaparti A2, Blokland M1, Nielen MW1, Saad KA2, Abushreeda WM2, Horvatovich P3, Al-Muraikhi AE2, Al-Maadheed M2, Georgakopoulos C2.

Publish date

2019 Oct 30;

PMID

31185502

Abstract

Chronic heart failure is the terminal stage of various cardiovascular diseases. Despite the availability of several classes of drugs, there is still an unmet need for effective treatment. Based on bench work during the past two decades, we have proposed that enhancement of β 2-adrenergic receptor signaling in combination with the presently preferred β 1-adrenergic receptor blockade would be a promising strategy. Chinese herbal medicines have been shown to be effective in the treatment of heart failure, although the mechanisms largely remain unknown. In the present study, we screened an herbal medicine compound/extract library for β-adrenergic receptor ligands to determine the target of certain effective botanical remedies and seek a leading compound(s) for chronic heart failure treatment. Using a high-throughput screening assay, we identified higenamine, which has a long history in chronic heart failure treatment in traditional Chinese medicine, to be a potent β-adrenergic receptor agonist. Further experiments using specific inhibitors showed that higenamine activated both β 1-adrenergic receptor and β 2-adrenergic receptor. Inhibition of its action by pertussis toxin (a Gi inhibitor) indicated that it is a β 2-adrenergic receptor Gs/Gi dual agonist. Contractility experiments demonstrated a positive inotropic effect of higenamine. In conclusion, we found an herbal compound, higenamine, to be a dual agonist for β 1/β 2-adrenergic receptors with no preference in stimulating the Gs and Gi pathways in β 2-adrenergic receptor signaling. Our results elucidated not only the target of higenamine to explain its pharmacological effect in treating chronic heart failure, but also the mechanisms of its cardiac toxicity.

Georg Thieme Verlag KG Stuttgart · New York.

Title

Higenamine, a Dual Agonist for β 1- and β 2-Adrenergic Receptors Identified by Screening a Traditional Chinese Medicine Library.

Author

Chen Y1, Guo B1, Zhang H1, Hu L2, Wang J1.

Publish date

2019 Jul