D-TetrahydropalmatineCAS# 3520-14-7 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 3520-14-7 | SDF | Download SDF |
| PubChem ID | 969488 | Appearance | Powder |
| Formula | C21H25NO4 | M.Wt | 355.41 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (13aR)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline | ||
| SMILES | COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC | ||
| Standard InChIKey | AEQDJSLRWYMAQI-QGZVFWFLSA-N | ||
| Standard InChI | InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | D-Tetrahydropalmatine is a organic cation transporter 1 (OCT1) inhibitor, it can obviously inhibit the uptake of monocrotaline (MCT) in MDCK-hOCT1 cells and isolate rat primary hepatocytes, and attenuate the viability reduction and LDH release of the primary cultured rat hepatocytes caused by MCT. |
| Targets | P450 (e.g. CYP17) | Dopamine Receptor |
| In vitro | Organic cation transporter 1 mediates the uptake of monocrotaline and plays an important role in its hepatotoxicity.[Pubmed: 23831208]Toxicology. 2013 Sep 15;311(3):225-30.Monocrotaline (MCT) is a kind of toxic retronecine-type pyrrolizidine alkaloids (PAs) from plants of Crotalaria, which can be bio-activated by cytochrome P450 (CYP) enzymes in liver and then induce hepatotoxicity. Since CYPs are localized in the endoplasmic reticulum, the influx of MCT to the liver is the key step for its hepatotoxicity. |
| Kinase Assay | Effects of tetrahydroprotoberberines on dopamine receptor subtypes in brain.[Pubmed: 2530755]hongguo Yao Li Xue Bao. 1989 Mar;10(2):104-10.The effects of 12 tetrahydroprotoberberines (THPBs) on D1 and D2 receptors labelled with [3H]DA, [3H]Sch-23390 and [3H]spiperone were evaluated. Their effects on the activity of adenylate cyclase stimulated with DA 40 mumols/L were also assessed. |
D-Tetrahydropalmatine Dilution Calculator
D-Tetrahydropalmatine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.8137 mL | 14.0683 mL | 28.1365 mL | 56.273 mL | 70.3413 mL |
| 5 mM | 0.5627 mL | 2.8137 mL | 5.6273 mL | 11.2546 mL | 14.0683 mL |
| 10 mM | 0.2814 mL | 1.4068 mL | 2.8137 mL | 5.6273 mL | 7.0341 mL |
| 50 mM | 0.0563 mL | 0.2814 mL | 0.5627 mL | 1.1255 mL | 1.4068 mL |
| 100 mM | 0.0281 mL | 0.1407 mL | 0.2814 mL | 0.5627 mL | 0.7034 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Organic cation transporter 1 mediates the uptake of monocrotaline and plays an important role in its hepatotoxicity.[Pubmed:23831208]
Toxicology. 2013 Sep 15;311(3):225-30.
Monocrotaline (MCT) is a kind of toxic retronecine-type pyrrolizidine alkaloids (PAs) from plants of Crotalaria, which can be bio-activated by cytochrome P450 (CYP) enzymes in liver and then induce hepatotoxicity. Since CYPs are localized in the endoplasmic reticulum, the influx of MCT to the liver is the key step for its hepatotoxicity. The objective of the present study was to investigate the role of organic cation transporter 1 (OCT1), a transporter mainly expressed in liver, in the uptake of MCT and in hepatotoxicity induced by MCT. The results revealed that MCT markedly inhibited the uptake of 1-methyl-4-phenylpyridinium (MPP(+)), an OCT1 substrate, in Madin-Darby canine kidney (MDCK) cells stably expressing human OCT1 (MDCK-hOCT1) with the IC50 of 5.52+/-0.56muM. The uptake of MCT was significantly higher in MDCK-hOCT1 cells than in MDCK-mock cells, and MCT uptake in MDCK-hOCT1 cells followed Michaelis-Menten kinetics with the Km and Vmax values of 25.0+/-6.7muM and 266+/-64pmol/mg protein/min, respectively. Moreover, the OCT1 inhibitors, such as quinidine, D-Tetrahydropalmatine (d-THP), obviously inhibited the uptake of MCT in MDCK-hOCT1 cells and isolated rat primary hepatocytes, and attenuated the viability reduction and LDH release of the primary cultured rat hepatocytes caused by MCT. In conclusion, OCT1 mediates the hepatic uptake of MCT and may play an important role in MCT induced-hepatotoxicity.
Effects of tetrahydroprotoberberines on dopamine receptor subtypes in brain.[Pubmed:2530755]
Zhongguo Yao Li Xue Bao. 1989 Mar;10(2):104-10.
The effects of 12 tetrahydroprotoberberines (THPBs) on D1 and D2 receptors labelled with [3H]DA, [3H]Sch-23390 and [3H]spiperone were evaluated. Their effects on the activity of adenylate cyclase stimulated with DA 40 mumols/L were also assessed. All of the l-THPBs tested behaved as DA receptor antagonists with preferential affinity toward the D1 receptors. Among them, l-stepholidine (l-SPD), a THPB analog with 2 hydroxy groups at the C2 and C10 positions, was the most potent. Its affinity toward D1 receptors was 4-7 times higher than that toward D2 receptors. The results suggest that the hydroxy groups in l-THPBs are very important factors in determining the affinity to DA receptors. Moreover, D-Tetrahydropalmatine (d-THP), a dextro-THPB analog, displayed no affinity for the D2 receptor subtype, while its optical isomer, l-THP, was a DA receptor antagonist. This indicates that the levo-optical configuration is necessary for the affinity of THPBs to DA receptors. In addition, l-SPD was 18 times more potent than haloperidol with respect to binding to D1 receptors, but 14 times weaker for D2 receptors. Thus, it is expected that the clinical effects of l-SPD can be distinguished from that of haloperidol.
