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Synephrine

$68

  • Brand : BIOFRON

  • Catalogue Number : BD-P0828

  • Specification : 98.5%(HPLC)

  • CAS number : 94-07-5

  • Formula : C9H13NO2

  • Molecular Weight : 167.21

  • PUBCHEM ID : 7172

  • Volume : 25mg

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Catalogue Number

BD-P0828

Analysis Method

Specification

98.5%(HPLC)

Storage

-20℃

Molecular Weight

167.21

Appearance

White powder

Botanical Source

This product is isolated and purified from the young fruits Citrus aurantium L.

Structure Type

Category

SMILES

CNCC(C1=CC=C(C=C1)O)O

Synonyms

synefrin/simpatol/4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]phenol/(-)-Oxedrine/oxedrine/(-)-Sympatol/(R)-4-(1-hydroxy-2-(methylamino)ethyl)phenol/1-(4-Hydroxyphenyl)-2-methylaminoethanol/synephrin/ethaphene/analeptin/simpalon/(-)-Synephrine/Benzenemethanol, 4-hydroxy-α-[(methylamino)methyl]-, (αR)-/Synephrine/D-synephrine/(-)-4-hydroxy-α-[(methylamino)methyl]benzenemethanol/sympathol/pentedrin/(-)-p-hydroxy-α-[(methylamino)methyl]benzyl alcohol

IUPAC Name

Applications

Characterization of antidepressant-like effects of p-synephrine stereoisomers.[Pubmed: 11485034]Naunyn Schmiedebergs Arch Pharmacol. 2001 Jul;364(1):21-6. We previously reported that p-Synephrine has antidepressant-like activity in the murine models of forced swimming and tail suspension. METHODS AND RESULTS: In the present study, we characterized antidepressant-like effects of p-Synephrine stereoisomers in both in vivo and in vitro systems. In the tail suspension test, S-(+)-p-Synephrine (3 mg/kg, p.o.) reduced the duration of immobility, while R-(-)-p-Synephrine (0.3-3 mg/kg, p.o.) had no effect. S-(+)-p-Synephrine (0.3, 1 and 3 mg/kg, p.o.) and R-(-)-p-Synephrine (1 mg/ kg and 3 mg/kg, p.o.) significantly reversed the reserpine (2.5 mg/kg, i.p.)-induced hypothermia. S-(+)-p-Synephrine was more effective than R-(-)-p-Synephrine in inhibition of both [3H]noradrenaline uptake in rat cerebral cortical slices (maximal inhibition 85.7 +/- 7.8% vs. 59.8 +/- 4.3%; EC50 5.8 +/- 0.7 microM vs. 13.5 +/- 1.2 microM) and [3H]nisoxetine binding (Ki 4.5 +/- 0.5 microM vs. 8.2 +/- 0.7 microM). In contrast, R-(-)-p-Synephrine was more effective than S-(+)-p-Synephrine in stimulation of [3H]noradrenaline release from rat cerebral cortical slices (maximal stimulation 23.9 +/- 1.8% vs. 20.1 +/- 1.7%; EC50 8.2 +/- 0.6 microM vs. EC50 12.3 +/- 0.9 microM). The stimulatory effect of R-(-)-p-Synephrine on [3H]noradrenaline release was inhibited by nisoxetine (100 nM), but tetrodotoxin (1 microM) and elimination of extracellular calcium had no effect. CONCLUSIONS: It is suggested that S-(+)-p-Synephrine has more effective antidepressant-like activity than R-(-)-p-Synephrine.

Density

1.2±0.1 g/cm3

Solubility

Methanol

Flash Point

163.4±14.3 °C

Boiling Point

341.1±27.0 °C at 760 mmHg

Melting Point

187 °C (dec.)(lit.)

InChl

InChl Key

YRCWQPVGYLYSOX-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:94-07-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

21075161

Abstract

Synephrine is cited as ‘the active component’ of plants and dietary supplements used in weight loss. It became one of the most popular stimulants present in weight-loss products after the US Food and Drug Administration had interdicted the use of ephedrine-containing dietary supplements. Synephrine is also a trace amine that can be found in vertebrates and invertebrates. Synephrine acts on several adrenergic and serotonergic receptors and its activity on trace-amine-associated receptors has long been discussed. Synephrine exists in three different positional isomers; however, only p- and m-synephrine have been described in weight-loss products. The alleged effectiveness of synephrine-containing supplements is attributed to the thermogenic effects arising from synephrine’s adrenergic stimulation. The growing use of synephrine has raised concerns since it has been accompanied by reports of adverse effects. Cardiac adverse events, including hypertension, tachyarrhythmia, variant angina, cardiac arrest, QT prolongation, ventricular fibrillation, myocardial infarction, and sudden death, have been the most common adverse effects associated with synephrine intake. The mechanisms involved in synephrine-induced cardiotoxicity are still unknown since studies related to its safety are scarce. This review will address general aspects concerning the pharmacology of synephrine, but will focus on the efficacy and toxicity aspects related to the use of synephrine in weight-loss.

Copyright © 2010 Elsevier Ltd. All rights reserved.

Title

Synephrine: from trace concentrations to massive consumption in weight-loss.

Author

Rossato LG1, Costa VM, Limberger RP, Bastos Mde L, Remião F.

Publish date

2011 Jan

PMID

28372211

Abstract

A LC-MS/MS method for synephrine as a biomarker for orange honey authenticity was developed and validated. The sample was extracted with 5% TCA and cleaned up with Florisil providing 83.7% recoveries. Ions transitions for quantification and identification were 168→135.0 and 168→107.0, respectively. The limits of detection and quantification were 0.66 and 1.0ng/g, respectively. Synephrine was detected in orange honey at levels from 79.2 to 432.2ng/g, but not in other monofloral honeys. It was also present in some wildflower honeys (9.4-236.5ng/g), showing contribution of citrus to this polyfloral honey. Results were confirmed by qualitative pollen analysis. No citrus pollen was detected in honey containing synephrine levels ≤43.8ng/g, suggesting that synephrine in honey is more sensitive compared to pollen analysis. Synephrine was found in citrus but not in other apiculture flowers. Therefore, synephrine is a botanical marker to differentiate and attest authenticity of orange honey.

Copyright © 2017 Elsevier Ltd. All rights reserved.

KEYWORDS

Amines; Biomarker; Botanical origin; Citrus honey; Honey; Orange honey; Synephrine; Synephrine (PubChem CID: 7172)

Title

Synephrine - A potential biomarker for orange honey authenticity.

Author

Tette PA1, Guidi LR1, Bastos EM2, Fernandes C3, Gloria MB4.

Publish date

2017 Aug 15

PMID

28532150

Abstract

To validate the suitability of synephrine, known to be a highly abundant alkaloid in oranges, as a dietary biomarker for orange consumption, a highly sensitive and robust stable isotope dilution analysis (SIDA) as well as an ECHO method, using the analyte itself as a pseudointernal standard injected into the analysis run to provide an “echo peak” of the analyte, was developed to quantitate synephrine by liquid chromatography-tandem mass spectrometry (LC-MS/MS) in citrus juices and human urine before and after the ingestion of orange juice. A citrus juice screening revealed high synephrine concentrations of 150-420 nmol/mL in orange (n = 11) and tangerine (n = 2) juices, whereas 20-100 times lower levels were found in juice from grapefruit (n = 14), lemon (n = 5), pomelo (n = 2), and lime (n = 4). Application of the SIDA to quantitate synephrine in sulfatase/glucuronidase-treated urine samples (n = 10) after orange juice consumption showed an increase of synephrine from trace levels (0.1 ± 0.1 nmol/mL) in the 2-day washout phase to a maximum concentration of 8.9 (±5.5) nmol/mL found 4 h after ingestion of orange juice. Whereas proline betaine was recently reported as a dietary biomarker indicating the ingestion of any citrus product and Chinese artichoke, synephrine can be used a reliable additional biomarker with high specificity for orange and tangerine.

KEYWORDS

ECHO quantitation; citrus; dietary biomarker; oranges; synephrine

Title

Synephrine as a Specific Marker for Orange Consumption.

Author

Bader M1, Lang T1, Lang R1, Hofmann T1,2.

Publish date

2017 Jun 14