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| | 3-[3-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINO]PROPYL]-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-2H-3-BENZAZEPIN-2-ONE HYDROCHLORIDE Basic information |
| Product Name: | 3-[3-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINO]PROPYL]-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-2H-3-BENZAZEPIN-2-ONE HYDROCHLORIDE | | Synonyms: | UL-FS49;ZATEBRADINE HYDROCHLORIDE;UL-FS49, 3-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2H-3-benzazepin-2-one hydrochloride;3-[3-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINO]PROPYL]-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-2H-3-BENZAZEPIN-2-ONE HYDROCHLORIDE;2H-3-Benzazepin-2-one, 3-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-, monohydrochloride;Zatebradine HCl;ULFS 49CL;Zatebradine dihydrochloride | | CAS: | 91940-87-3 | | MF: | C26H37ClN2O5 | | MW: | 493.04 | | EINECS: | | | Product Categories: | Ion transporter and other ion channel | | Mol File: | 91940-87-3.mol | ![3-[3-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINO]PROPYL]-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-2H-3-BENZAZEPIN-2-ONE HYDROCHLORIDE Structure](CAS/GIF/91940-87-3.gif) |
| | 3-[3-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINO]PROPYL]-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-2H-3-BENZAZEPIN-2-ONE HYDROCHLORIDE Chemical Properties |
| Melting point | 188° and mp 168° | | storage temp. | 2-8°C | | solubility | H2O: ~14 mg/mL | | form | solid | | color | white | | Water Solubility | Soluble in water (100mM) |
| | 3-[3-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINO]PROPYL]-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-2H-3-BENZAZEPIN-2-ONE HYDROCHLORIDE Usage And Synthesis |
| Originator | ZATEBRADINE
HYDROCHLORIDE,Boenhringer
Ingelheim | | Uses | Zatebradine Hydrochloride exhibits bradycardic properties and blocks the hyperpolarization-activated cyclic nucleotide-gated (HCN). It is also a sinus node inhibitor. | | Manufacturing Process | A suspension of 1-[7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl]-3-
(N-benzylmethylamino)propane and 10% palladium-on-charcoal in glacial
acetic acid was hydrogenated at 50°C and at a hydrogen pressure of 5 bar.
After the catalyst had been filtered off, the solvent was evaporated in vacuum,
and the residue was taken up in methylene chloride. After the solution had
been extracted with an aqueous sodium bicarbonate solution and washed with
water, it was dried over magnesium sulfate, evaporated and purified over
silica gel with methylene chloride and then with increasing amounts of
methanol (up to 10%). The N-[3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-
benzazepin-2-one-3-yl)propyl]methylamine hydrochloride. Yield: 87% of
theory. Melting point: 110°C (dec.).
1.26 g (20 mmols) of sodium cyanoborohydride were added to a solution of
3.29 g (10 mmols) of N-[3-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-
benzazepin-2-one-3-yl)propyl]methylamine hydrochloride and 1.8 g (10
mmol) of 2-(3,4-dimethoxyphenyl)acetaldehyde in 40 ml of ethanol, while
maintaining a pH of 6-7 by the addition of 2 N hydrochloric acid, and stirring
was continued for 48 h at room temperature. After evaporating the solution in
vacuum, the residue was taken up in dilute hydrochloric acid and extracted
twice with ether. Subsequently, the aqueous phase was made alkaline and
extracted three times with methylene chloride, and the organic phase was
evaporated and purified on silica gel. The 1-[7,8-dimethoxy-1,3,4,5-
tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{3,4-
dimethoxyphenyl}ethyl)amino]propane was obtained. | | Therapeutic Function | Bradycardic | | Biological Activity | Bradycardic agent that produces use-dependent inhibition of hyperpolarization-activated current (I f ) in sinoatrial node cells (EC 50 = 480 nM) and Purkinje fibres. Displays negative chronotropic activity in isolated guinea pig atria (EC 50 of 13.4 μ M). | | Biochem/physiol Actions | Zatebradine is a bradycardiac agent. | | storage | +4°C (desiccate) |
| | 3-[3-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]METHYLAMINO]PROPYL]-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-2H-3-BENZAZEPIN-2-ONE HYDROCHLORIDE Preparation Products And Raw materials |
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