- Naftopidil
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- $40.00 / 500mg
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2025-12-22
- CAS:57149-07-2
- Min. Order:
- Purity: 99.97%
- Supply Ability: 10g
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| | Naftopidil dihydrochloride Basic information |
| Product Name: | Naftopidil dihydrochloride | | Synonyms: | (+-)-1-(4-(2-methoxyphenyl)piperazinyl)-3-(1-naphthyloxy)propan-2-ol;4-(2-methoxyphenyl)-alpha-((1-naphthalenyloxy)methyl)-1-pioerazineethano;4-(2-methoxyphenyl)-alpha-((1-naphthalenyloxy)methyl)-1-pioerazineethanol;kt-611;NAFTOPIDIL DIHYDROCHLORIDE (KT-611) A1 A DRENOCEPTOR ANTAG;NAFTOPIDIL;1-[4-(2-methoxyphenyl)-1-piperazinyl]-3-(1-naphthalenyloxy)-2-propanol dihydrochloride;Nafitopidil | | CAS: | 57149-07-2 | | MF: | C24H28N2O3 | | MW: | 392.49 | | EINECS: | 692-531-5 | | Product Categories: | AVISHOT;Intermediates & Fine Chemicals;Pharmaceuticals;Adrenoceptor | | Mol File: | 57149-07-2.mol |  |
| | Naftopidil dihydrochloride Chemical Properties |
| Melting point | 127 °C | | Boiling point | 517.2°C (rough estimate) | | density | 1.1592 (rough estimate) | | refractive index | 1.6300 (estimate) | | storage temp. | Sealed in dry,Room Temperature | | solubility | methanol: >10 mg/mL | | pka | 14.01±0.20(Predicted) | | form | solid | | color | white | | Merck | 14,6356 | | InChI | InChI=1S/C24H28N2O3/c1-28-24-11-5-4-10-22(24)26-15-13-25(14-16-26)17-20(27)18-29-23-12-6-8-19-7-2-3-9-21(19)23/h2-12,20,27H,13-18H2,1H3 | | InChIKey | HRRBJVNMSRJFHQ-UHFFFAOYSA-N | | SMILES | C12C=CC=CC1=CC=CC=2OCC(O)CN1CCN(C2C=CC=CC=2OC)CC1 | | CAS DataBase Reference | 57149-07-2(CAS DataBase Reference) |
| RIDADR | 3077 | | WGK Germany | 3 | | RTECS | TL9336500 | | HS Code | 29335990 | | Toxicity | LD50 in mice, rats (g/kg): 1.3, 6.4 orally (Himmel) |
| | Naftopidil dihydrochloride Usage And Synthesis |
| Description | Naftopidil was launched in Japan for the treatment of dysuria
associated with benign prostatic hypertrophy (BPH). It can be prepared by a two
step route starting with α-naphthol. Naftopidil is a potent postsynaptic-selective
alpha-l-antagonist with a slightly higher affinity for the human prostatic than for
the aortic alpha-adrenoceptor. It also shows a 5-HT1A agonistic effect, as well
as a weak calcium antagonistic activity, but no alpha-2 or beta-adrenoreceptor
affinity. In experiments with rats or rabbits, Naftopidil was shown to be more
potent and selective for the urodynamic effect than the hypotensive effect.
Aromatic or aliphatic hydroxylation are the major routes of metabolism,
producing metabolites with a profile similar to the parent compound. | | Chemical Properties | Off-White Solid | | Originator | Boehringer Mannheim (Germany) | | Uses | Naftopidil is an α-1-adrenergic receptor antagonist. Naftopidil is used as an antihypertensive. | | Uses | A α-1-Adrenergic receptor antagonist, antihypertensive. | | Uses | antihypertensive, alpha-blocker, 5HT1a agonist | | Definition | ChEBI: Naftopidil is a member of piperazines. | | Brand name | Avishot;Flivas | | Biological Activity | An α 1 -adrenoceptor antagonist with only weak antagonism at post-junctional α 2 receptors; a potent, persistent antihypertensive and vasodilator. | | Synthesis | The general procedure for the synthesis of 1-(4-(2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-2-ol from 3-(1-naphthyloxy)-1,2-epoxypropane and 1-(2-methoxyphenyl)piperazine was as follows: with reference to the synthesis of Example 1 (RS)-naphthalenophenedil (HUHS1001), to a solution of 2-((1-naphthyloxy)methyl) ethylene oxide (100 mg, 0.50 mmol) to a solution of 2-(2-methoxyphenyl)piperazine (95 μL, 0.60 mmol) in ethanol (1 mL). The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford (RS)-naphthodil (199 mg, 100% yield). The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3) and ESI-HRMS (cation, sodium formate).1H-NMR data were as follows: δ 2.72-2.76 (m, 4H), 2.92-2.95 (m, 2H), 3.09-3.18 (m, 4H), 3.87 (s, 3H), 4.16 (dd, J = 9.6 and 5.0 Hz, 1H), 4.24 (dd, J = 9.6 and 5.0 Hz, 1H), 4.28-4.34 (m, 1H), 6.84 (d, J = 7.8 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H), 6.91-6.98 (m, 2H), 7.00-7.04 (m, 1H), 7.39 (t , J = 8.2 Hz, 1H), 7.44 (d, J = 8.2 Hz, 1H), 7.47-7.51 (m, 2H), 7.79-7.81 (m, 1H), 8.26-8.29 (m, 1H).ESI-HRMS (cation, sodium formate) Calculated value: C24H29N2O3 ([M + H]+) m/z 393.2173 , measured value 393.2148. | | References | [1] Patent: US2015/353473, 2015, A1. Location in patent: Paragraph 0179-0181
[2] Patent: JP6041303, 2016, B2. Location in patent: Paragraph 0064-0066
[3] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3713 - 3722
[4] Patent: US3997666, 1976, A |
| | Naftopidil dihydrochloride Preparation Products And Raw materials |
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