HirsuteineCAS# 35467-43-7 |
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| Cas No. | 35467-43-7 | SDF | Download SDF |
| PubChem ID | 3037151 | Appearance | Powder |
| Formula | C22H26N2O3 | M.Wt | 366.45 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | methyl (E)-2-[(2S,3R,12bR)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate | ||
| SMILES | COC=C(C1CC2C3=C(CCN2CC1C=C)C4=CC=CC=C4N3)C(=O)OC | ||
| Standard InChIKey | TZUGIFAYWNNSAO-AZQGJTAVSA-N | ||
| Standard InChI | InChI=1S/C22H26N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h4-8,13-14,17,20,23H,1,9-12H2,2-3H3/b18-13+/t14-,17-,20+/m0/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 | Hirsuteine exhibits potent neuroprotective effects against glutamate-induced HT22 cell death. Hirsuteine non-competitively antagonizes nicotine-evoked dopamine release by blocking ion permeation through nicotinic receptor channel complexes. |
| Targets | Dopamine Receptor |
| In vitro | Non-competitive antagonism by hirsuteine of nicotinic receptor-mediated dopamine release from rat pheochromocytoma cells.[Pubmed: 8320880]Jpn J Pharmacol. 1993 Apr;61(4):351-6.Effects of Hirsuteine, an indole alkaloid extracted from Uncaria genus, on nicotine- and high K-induced responses were investigated in rat pheochromocytoma PC12 cells.
Alkaloids from the hook-bearing branch of Uncariarhynchophylla and their neuroprotective effects against glutamate-induced HT22 cell death.[Pubmed: 24899363]J Asian Nat Prod Res. 2014;16(8):876-83.
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Hirsuteine Dilution Calculator
Hirsuteine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.7289 mL | 13.6444 mL | 27.2889 mL | 54.5777 mL | 68.2221 mL |
| 5 mM | 0.5458 mL | 2.7289 mL | 5.4578 mL | 10.9155 mL | 13.6444 mL |
| 10 mM | 0.2729 mL | 1.3644 mL | 2.7289 mL | 5.4578 mL | 6.8222 mL |
| 50 mM | 0.0546 mL | 0.2729 mL | 0.5458 mL | 1.0916 mL | 1.3644 mL |
| 100 mM | 0.0273 mL | 0.1364 mL | 0.2729 mL | 0.5458 mL | 0.6822 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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Alkaloids from the hook-bearing branch of Uncariarhynchophylla and their neuroprotective effects against glutamate-induced HT22 cell death.[Pubmed:24899363]
J Asian Nat Prod Res. 2014;16(8):876-83.
One new alkaloid, 4-geissoschizine N-oxide methyl ether (1), was isolated from the EtOH extract of the hook-bearing branch of Uncariarhynchophylla, together with 10 known alkaloids, 3-epi-geissoschizine methyl ether (2) isolated from U.rhynchophylla for the first time, geissoschizine methyl ether (3), 4-Hirsuteine N-oxide (4), Hirsuteine (5), hirsutine (6), 3alpha-dihydro-cadambine (7), 3beta-isodihydro-cadambine (8), cadambine (9), strictosamide (10), and akuammigine (11). The structures were elucidated by spectroscopic methods including UV, ESI-QTOF MS, NMR, and circular dichroism experiments. Neuroprotective effects of 1-9 were investigated against 3 mM glutamate-induced HT22 cell death. The activity assay showed that 2, 3, 5, and 6 exhibited potent neuroprotective effects against glutamate-induced HT22 cell death. However, only weak neuroprotective activities were observed for 1, 4, 7, 8, and 9.
Non-competitive antagonism by hirsuteine of nicotinic receptor-mediated dopamine release from rat pheochromocytoma cells.[Pubmed:8320880]
Jpn J Pharmacol. 1993 Apr;61(4):351-6.
Effects of Hirsuteine, an indole alkaloid extracted from Uncaria genus, on nicotine- and high K-induced responses were investigated in rat pheochromocytoma PC12 cells. Hirsuteine (300 nM-10 microM) inhibited dopamine release evoked by 100 microM nicotine in a concentration-dependent manner. Hirsuteine did not produce a parallel shift of the concentration-response relationship curve for nicotine, but reduced maximal dopamine release. Dopamine release evoked by 60 and 155 mM KCl was also inhibited by Hirsuteine, but the concentration necessary for significant inhibition was higher (more than 10 microM). Under whole cell voltage-clamp, Hirsuteine reversibly inhibited inward currents activated by 100 microM nicotine. The current inhibition was slightly accelerated by hyperpolarization. The results suggest that Hirsuteine non-competitively antagonizes nicotine-evoked dopamine release by blocking ion permeation through nicotinic receptor channel complexes. The blockade of Ca channels, which are activated during nicotine-evoked depolarization, may not play a major role in the antagonism.
