| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Synephrine tartrate targets adrenergic receptors (Adrenergic Receptor), specifically functioning as an α-adrenergic and β-adrenergic agonist. It acts on both α and β subtypes of the adrenergic receptor family, which are G protein-coupled receptors (GPCRs) involved in the sympathetic nervous system. As an endogenous metabolite, synephrine mimics the effects of endogenous catecholamines like epinephrine and norepinephrine. The compound exhibits agonistic activity at β-3 adrenergic receptors, which are implicated in lipolysis and energy expenditure, contributing to its use in weight loss supplements. Synephrine tartrate does not readily cross the blood-brain barrier due to its polar nature, limiting central nervous system effects.
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| ln Vitro |
In vitro studies demonstrate that Synephrine tartrate acts as an agonist at adrenergic receptors, stimulating adenylate cyclase activity and increasing intracellular cAMP levels in cells expressing these receptors. The compound exhibits concentration-dependent activation of β-adrenergic receptors, with EC50 values in the micromolar range depending on the receptor subtype and cell type. In isolated tissue preparations, synephrine produces vasoconstriction in blood vessels and relaxation of bronchial smooth muscle, consistent with its sympathomimetic profile. The compound shows greater potency at β-3 receptors compared to β-1 and β-2 subtypes, which explains its preferential effects on metabolic tissues. Binding affinity studies using radiolabeled ligands demonstrate that synephrine competitively displaces [3H]-dihydroalprenolol from β-adrenergic receptor binding sites with Ki values in the range of 1-10 µM. The compound exhibits no significant activity at nicotinic or muscarinic receptors, indicating selectivity for the adrenergic system.In cell-based assays, Synephrine tartrate is evaluated for its effects on adrenergic receptor signaling in various cell lines. HEK-293 cells stably expressing human β-3 adrenergic receptors are seeded in 96-well plates at 5 × 10^4 cells/well and cultured for 24 hours. Cells are treated with various concentrations of synephrine tartrate (0.01-100 µM) for 15-30 minutes at 37°C. Intracellular cAMP levels are measured using a competitive ELISA or HTRF-based cAMP detection kit according to the manufacturer's protocol. The EC50 for cAMP accumulation is calculated from dose-response curves. For calcium mobilization assays, CHO cells expressing α-1 adrenergic receptors are loaded with Fluo-4 AM calcium indicator dye (5 µM) for 30 minutes at 37°C. Cells are stimulated with synephrine tartrate, and fluorescence intensity is measured using a fluorescence plate reader. Cytotoxicity is assessed using MTT assays, showing no significant reduction in cell viability at concentrations up to 100 µM.
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| ln Vivo |
Synephrine (1 mg/kg; oral gavage; 8 days; PVL and BDL rats) significantly improved the hyperdynamic state of PVL and BDL rats. After synephrine treatment, portal venous pressure, portal blood flow and cardiac index were significantly reduced in PVL and BDL rats, while mean arterial pressure and systemic and portal regional vascular resistance were enhanced [2].
In in vivo animal studies, Synephrine tartrate has been evaluated for its hemodynamic effects in portal hypertensive rats. In a study by Huang et al., synephrine (1 mg/kg per 12 hours; oral gavage for 8 days) significantly ameliorated the hyperdynamic state in both portal vein ligation (PVL) and bile duct ligation (BDL) rats. The portal venous pressure in PVL and BDL rats, portal tributary blood flow, and cardiac index were significantly reduced, while mean arterial pressure and systemic as well as portal territory vascular resistance were enhanced by treatment with synephrine. These findings demonstrate the compound's vasoconstrictor and pressor effects in vivo. In other animal models, synephrine has been shown to increase metabolic rate and promote lipolysis, consistent with its β-3 adrenergic agonist activity. The compound exhibits dose-dependent effects on heart rate and blood pressure, with higher doses producing significant cardiovascular changes. |
| Enzyme Assay |
The in vitro enzyme/receptor binding assay for Synephrine tartrate typically involves competitive radioligand binding using membrane preparations from cells or tissues expressing adrenergic receptors. Membranes are prepared from transfected HEK-293 cells expressing human β-1, β-2, or β-3 adrenergic receptors by homogenization in ice-cold 50 mM Tris-HCl buffer (pH 7.4) containing 5 mM EDTA and protease inhibitors. Membranes (10-50 µg protein) are incubated with [3H]-dihydroalprenolol (0.5-2 nM) in assay buffer (50 mM Tris-HCl pH 7.4, 10 mM MgCl2) for 60 minutes at 25°C. Various concentrations of Synephrine tartrate (0.1 nM to 1 mM) are added to competition tubes. Non-specific binding is determined using 10 µM propranolol. Bound ligand is separated by rapid filtration through GF/B glass fiber filters, followed by three washes with ice-cold buffer. Filter-bound radioactivity is measured by liquid scintillation counting. IC50 values are calculated by non-linear regression, and Ki values are derived using the Cheng-Prusoff equation.
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| Cell Assay |
For in vitro cell-based assays, HEK-293 cells stably expressing human β-3 adrenergic receptors are cultured in DMEM supplemented with 10% FBS, 100 U/mL penicillin, and 100 µg/mL streptomycin at 37°C in 5% CO2. Cells are seeded in 96-well plates at 5 × 10^4 cells/well and allowed to attach overnight. The following day, cells are washed with PBS and serum-starved for 4 hours in serum-free medium. Synephrine tartrate is prepared as a stock solution in distilled water and diluted in assay buffer (HBSS containing 20 mM HEPES, 0.1% BSA, and 500 µM IBMX) to final concentrations of 0.01, 0.1, 1, 10, 50, and 100 µM. Cells are treated with the compound for 30 minutes at 37°C. The reaction is terminated by aspirating the medium and adding lysis buffer. Intracellular cAMP levels are measured using a homogeneous time-resolved fluorescence (HTRF) cAMP detection kit. Fluorescence ratios are measured at 665 nm and 620 nm using a microplate reader. EC50 values are calculated from dose-response curves fitted to a four-parameter logistic equation using GraphPad Prism software. Positive controls include isoproterenol (β-adrenergic agonist) and forskolin (direct adenylyl cyclase activator).
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| Animal Protocol |
Animal/Disease Models: portal vein ligation (PVL) or bile duct ligation (BDL) rats [2].
Doses: 1 mg/kg every 12 hrs (hrs (hours)). Route of Administration: po (oral gavage); for 8 days. Experimental Results: Portal venous pressure, portal blood flow and cardiac index in PVL and BDL rats were Dramatically diminished, and mean arterial pressure, systemic and portal regional blood vessels were Dramatically diminished. Resistance increases. In in vivo animal studies, male Sprague-Dawley rats (250-300 g) are used for portal hypertension models. Portal vein ligation (PVL) is performed under ketamine/xylazine anesthesia by partial ligation of the portal vein. Bile duct ligation (BDL) is performed by double ligation and section of the bile duct. After 14 days, rats are treated with Synephrine tartrate (1 mg/kg per 12 hours) by oral gavage for 8 consecutive days. Hemodynamic measurements are performed under anesthesia with pentobarbital (50 mg/kg, intraperitoneal). A PE-50 catheter is inserted into the femoral artery for mean arterial pressure (MAP) measurement. Portal venous pressure (PVP) is measured via a catheter inserted into the ileocolic vein. Portal tributary blood flow (PTBF) is measured using a transit-time flow probe placed around the superior mesenteric artery. Cardiac index (CI) is calculated from cardiac output measured by thermodilution. Systemic vascular resistance (SVR) and portal territory vascular resistance (PVR) are calculated from MAP and PVP measurements. Data are expressed as mean ± SEM, and statistical analysis is performed using ANOVA. |
| References |
| Molecular Formula |
C22H32N2O10
|
|---|---|
| Molecular Weight |
484.4969
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| Exact Mass |
317.111
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| CAS # |
16589-24-5
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| Related CAS # |
Synephrine;94-07-5;Synephrine hydrochloride;5985-28-4
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| PubChem CID |
101532
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.159 g/cm3
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| Boiling Point |
823.3ºC at 760 mmHg
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| Melting Point |
184 °C
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| Flash Point |
451.7ºC
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| Vapour Pressure |
1.08E-28mmHg at 25°C
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| Index of Refraction |
13 ° (C=5, H2O)
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| Source |
Originated from plants: Rutaceae Citrus reticulata Blanco
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| tPSA |
220.04
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| Hydrogen Bond Donor Count |
10
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
34
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| Complexity |
256
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| Defined Atom Stereocenter Count |
2
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| SMILES |
O([H])[C@]([H])(C1C([H])=C([H])C(=C([H])C=1[H])O[H])C([H])([H])N([H])C([H])([H])[H].O([H])[C@]([H])(C1C([H])=C([H])C(=C([H])C=1[H])O[H])C([H])([H])N([H])C([H])([H])[H].O([H])C([H])(C(=O)O[H])C([H])(C(=O)O[H])O[H]
|
| InChi Key |
KZZBAIXGUQOHKI-CEAXSRTFSA-N
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| InChi Code |
InChI=1S/2C9H13NO2.C4H6O6/c2*1-10-6-9(12)7-2-4-8(11)5-3-7;5-1(3(7)8)2(6)4(9)10/h2*2-5,9-12H,6H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1
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| Chemical Name |
(2R,3R)-2,3-dihydroxybutanedioic acid;4-[1-hydroxy-2-(methylamino)ethyl]phenol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0640 mL | 10.3199 mL | 20.6398 mL | |
| 5 mM | 0.4128 mL | 2.0640 mL | 4.1280 mL | |
| 10 mM | 0.2064 mL | 1.0320 mL | 2.0640 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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