Synephrine
(Synonyms: 辛弗林; Oxedrine) 目录号 : GC38438Synephrine (Oxedrine), a natural protoalkaloid in the extract of bitter orange and other citrus species, is commonly used for weight loss.
Cas No.:94-07-5
Sample solution is provided at 25 µL, 10mM.
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Synephrine (Oxedrine), a natural protoalkaloid in the extract of bitter orange and other citrus species, is commonly used for weight loss.
Synephrine is a compound commonly used for weight loss. Synephrine has gained significant popularity as an alternative to ephedrine. Products containing bitter orange or synephrine are suspected of causing adverse cardiovascular reactions. [1] [2] Synephrine can stimulate glucose consumption (Glut4-dependent glucose uptake) by stimulating AMPK activity, regardless of insulin-stimulated PI3 kinase-Akt activity in L6 skeletal muscle cells. [3]
LD50: Mice >1000mg/kg (s.c.) [4]
[1] Stohs SJ, et al. Int J Med Sci, 2012, 9(7), 527-538. [2] Haaz S, et al. Obes Rev, 2006, 7(1), 79-88. [3] Hong NY, et al. Biochem Biophys Res Commun, 2012, 418(4), 720-724.
Cas No. | 94-07-5 | SDF | |
别名 | 辛弗林; Oxedrine | ||
Canonical SMILES | OC(C1=CC=C(O)C=C1)CNC | ||
分子式 | C9H13NO2 | 分子量 | 167.21 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 5.9805 mL | 29.9025 mL | 59.805 mL |
5 mM | 1.1961 mL | 5.9805 mL | 11.961 mL |
10 mM | 0.5981 mL | 2.9903 mL | 5.9805 mL |
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给药剂量 | mg/kg | 动物平均体重 | g | 每只动物给药体积 | ul | 动物数量 | 只 | |||
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工作液浓度: mg/ml;
DMSO母液配制方法: mg 药物溶于 μL DMSO溶液(母液浓度 mg/mL,
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1. 首先保证母液是澄清的;
2.
一定要按照顺序依次将溶剂加入,进行下一步操作之前必须保证上一步操作得到的是澄清的溶液,可采用涡旋、超声或水浴加热等物理方法助溶。
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[Synephrine in dietary supplements and specialized foodstuffs: biological activity, safety and methods of analysis]
Vopr Pitan 2021;90(6):101-113.PMID:35032130DOI:10.33029/0042-8833-2021-90-6-101-113.
Synephrine is a natural protoalkaloid of the bitter orange Citrus aurantium L., it has structural similarity to ephedrine and adrenaline. Synephrine in the form of bitter orange extract is widely used as an ingredient of dietary supplements (DS) and specialized foodstuffs (SF) intended for weight loss and fitness improvement. Along with thermogenic and lipolytic effects, Synephrine can cause cardiovascular side effects, especially when combined with caffeine and physical activity. This aspect is important, insofar as the main consumers of weight loss products are overweight people who are at risk of developing cardiovascular diseases. The aim of the research is a hygienic assessment of the usage of bitter orange extract and Synephrine in DS and SF, which includes an analysis of approaches to technical regulation in the Russian Federation and abroad, a review of data on biological activity, safety, types of adulteration and methods for the determination of citrus protoalkaloids. Results. The adrenergic effect of bitter orange is caused by the presence of R-(-)-psynephrine, making up about 90% or more of the total protoalkaloids. Dry bitter orange fruit extracts, standardized to Synephrine content, which can vary from 4 to 98%, are used in the production of DS and SF. Synephrine is a weak adrenergic agonist, acting primarily through β3-adrenergic receptors, stimulating lipolysis. Because of insufficient safety data, the consumption of Synephrine is regulated in the Russian Federation and abroad. The upper permissible level of Synephrine consumption in the Russian Federation is 30 mg per day. Various cases of adulteration of DS and SF for weight loss and sport nutrition have been revealed: undeclared addition of Synephrine in the form of bitter orange extract, addition of synthetic Synephrine, its isomers or analogs. The main method for the determination of Synephrine and other biogenic amines in DS and SF is high performance liquid chromatography with ultraviolet and/or mass detection. Conclusion. The data presented in the review confirm the feasibility of developing an official method for determination of main protoalkaloids and monitoring of DS and SF for the content of Synephrine and other citrus protoalkaloids on its basis.
Synephrine: from trace concentrations to massive consumption in weight-loss
Food Chem Toxicol 2011 Jan;49(1):8-16.PMID:21075161DOI:10.1016/j.fct.2010.11.007.
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.
[Risk assessment of Synephrine in dietary supplements]
Bundesgesundheitsblatt Gesundheitsforschung Gesundheitsschutz 2017 Mar;60(3):323-331.PMID:28058460DOI:10.1007/s00103-016-2506-5.
Synephrine is a sympathomimetic phenylethylamine derivative that occurs naturally in citrus fruits. It is often added to dietary supplements intended for weight loss and enhancement of sports performance, typically in the form of Citrus aurantium extracts and in many cases in combination with caffeine. The health risks of Synephrine were evaluated on the basis of the available toxicological data and in accordance to the EFSA guidance on the safety assessment of botanicals and botanical preparations intended for use in food supplements. In animal studies, orally applied Synephrine induced adrenergic effects on the cardiovascular system (increase of blood pressure, ventricular arrhythmias), which were enhanced by the concomitant application of caffeine as well as physical activity. Some human intervention studies investigating the acute effects of Synephrine on blood pressure and heart rate of healthy, normotensive test persons indicate that Synephrine can induce cardiovascular effects in humans. A series of published case reports of adverse cardiovascular effects (hypertension, cardiac arrhythmia, myocardial infarction) were associated with consumption of synephrine- and caffeine-containing dietary supplements. In conclusion, consumption of high amounts of Synephrine, especially in combination with caffeine and physical exercise, is associated with an increased risk of adverse effects on the cardiovascular system. According to the assessment by the BfR (Bundesinstitut für Risikobewertung), daily intake of Synephrine through dietary supplements should not exceed the median intake from conventional foods.
Effects of ingesting a pre-workout dietary supplement with and without Synephrine for 8 weeks on training adaptations in resistance-trained males
J Int Soc Sports Nutr 2017 Jan 3;14:1.PMID:28096757DOI:10.1186/s12970-016-0158-3.
Background: The purpose of this study was to examine whether ingesting a pre-workout dietary supplement (PWS) with and without Synephrine (S) during training affects training responses in resistance-trained males. Methods: Resistance-trained males (N = 80) were randomly assigned to supplement their diet in a double-blind manner with either a flavored placebo (PLA); a PWS containing beta-alanine (3 g), creatine nitrate as a salt (2 g), arginine alpha-ketoglutarate (2 g), N-Acetyl-L-Tyrosine (300 mg), caffeine (284 mg), Mucuna pruiriens extract standardized for 15% L-Dopa (15 mg), Vitamin C as Ascorbic Acid (500 mg), niacin (60 mg), folate as folic acid (50 mg), and Vitamin B12 as Methylcobalamin (70 mg); or, the PWS supplement with Citrus aurantium extract containing 20 mg of Synephrine (PWS + S) once per day for 8-weeks during training. Participants donated a fasting blood sample and had body composition (DXA), resting heart rate and blood pressure, cognitive function (Stroop Test), readiness to perform, bench and leg press 1 RM, and Wingate anaerobic capacity assessments determined a 0, 4, and 8-weeks of standardized training. Data were analyzed by MANOVA with repeated measures. Performance and cognitive function data were analyzed using baseline values as covariates as well as mean changes from baseline with 95% confidence intervals (CI). Blood chemistry data were also analyzed using Chi-square analysis. Results: Although significant time effects were seen, no statistically significant overall MANOVA Wilks' Lambda interactions were observed among groups for body composition, resting heart and blood pressure, readiness to perform questions, 1RM strength, anaerobic sprint capacity, or blood chemistry panels. MANOVA univariate analysis and analysis of changes from baseline with 95% CI revealed some evidence that cognitive function and 1RM strength were increased to a greater degree in the PWS and/or PWS + S groups after 4- and/or 8-weeks compared to PLA responses. However, there was no evidence that PWS + S promoted greater overall training adaptations compared to the PWS group. Dietary supplementation of PWS and PWS + S did not increase the incidence of reported side effects or significantly affect the number of blood values above clinical norms compared to PLA. Conclusion: Results provide some evidence that 4-weeks of PWS and/or PWS + S supplementation can improve some indices of cognitive function and exercise performance during resistance-training without significant side effects in apparently health males. However, these effects were similar to PLA responses after 8-weeks of supplementation and inclusion of Synephrine did not promote additive benefits. Trial registration: This trial (NCT02999581) was retrospectively registered on December 16th 2016.
Electrochemical determination of Synephrine by using nafion/UiO-66/graphene-modified screen-printed carbon electrode
Curr Res Food Sci 2022 Jul 20;5:1158-1166.PMID:35899039DOI:10.1016/j.crfs.2022.07.008.
The screen-printed carbon electrode (SPCE) was one step modified with graphene (GN) and UiO-66 composites in nafion solution as a portable sensor (nafion/UiO-66/GN/SPCE) for the detection of Synephrine. The used GN and UiO-66 were well-characterized, exhibiting typical structures by scanning electron microscope (SEM) with energy dispersive spectroscopy (EDS), X-ray powder diffraction (XRD), and Fourier transform infrared spectroscopy (FTIR). The nafion/UiO-66/GN/SPCE showed the maximum electrochemical signals for Synephrine when comparing fabricated components in the cyclic voltammetric method. It was systematically investigated in modifier composition, modification volumes, pH, scan rate, and quantitative analysis ability. Under optimal conditions, the sensor exhibited a good detection limit (0.04 μmol L-1) for Synephrine with a linear range of 0.5 μmol L-1 to 60 μmol L-1 (r2 = 0.995). The nafion/UiO-66/GN/SPCE had adequate reproducibility and stability with relative standard deviations lower than 2.01%. It was also applied to determine Synephrine in the extract of Citrus aurantium L. with recoveries between 99.0% and 102.0%. The content of Synephrine was in good agreement with that of the HPLC method. Based on its convenience and stability, the proposed nafion/UiO-66/GN/SPCE could be further developed as a portable and rapid detection sensor for natural active compounds in food, agricultural, and pharmaceutical fields.