Naftopidil

Base Information

• Chemical Name: Naftopidil
• CAS No.: 57149-07-2
• Molecular Formula: C24H28N2O3
• Molecular Weight: 392.498
• Hs Code.: 29335990
• European Community (EC) Number: 692-531-5
• NSC Number: 759293
• UNII: R9PHW59SFN
• DSSTox Substance ID: DTXSID5045176
• Nikkaji Number: J82.340F
• Wikipedia: Naftopidil
• Wikidata: Q6958243
• NCI Thesaurus Code: C72927
• Pharos Ligand ID: 7QBKGVMQ14Z1
• Metabolomics Workbench ID: 153143
• ChEMBL ID: CHEMBL142635
• Mol file: 57149-07-2.mol

Synonyms:1-(4-(2-methoxyphenyl)-1-piperazinyl)-3-(1-naphthyloxy)-2-propanol;naftopidil

Chemical Property of Naftopidil

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 2.22E-15mmHg at 25°C
• Melting Point: 127 °C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 602.8 °C at 760 mmHg
• PKA: 14.01±0.20(Predicted)
• Flash Point: 318.3 °C
• PSA: 45.17000
• Density: 1.184 g/cm³
• LogP: 3.41320
• Storage Temp.: Store at RT
• Solubility.: methanol: >10 mg/mL
• Water Solubility.: methanol: >10 mg/mL
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 392.20999276
• Heavy Atom Count: 29
• Complexity: 483

Purity/Quality:

99% ^*data from raw suppliers

Naftopidil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=CC=C1N2CCN(CC2)CC(COC3=CC=CC4=CC=CC=C43)O
• Recent ClinicalTrials: Efficacy And Safety Study Of Naftopidil to Patients Treatment With LUTS
• Recent NIPH Clinical Trials: Study of efficacy of alpha1AR inhibitors for FBD
• 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.
• Uses: Naftopidil is an α-1-adrenergic receptor antagonist. Naftopidil is used as an antihypertensive. A α-1-Adrenergic receptor antagonist, antihypertensive. antihypertensive, alpha-blocker, 5HT1a agonist

Technology Process of Naftopidil

There total 7 articles about Naftopidil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-(1-naphthyloxy)-1,2-epoxypropane (2461-42-9) + 1-(2-Methoxyphenyl)piperazine (35386-24-4) → naftopidil (57149-07-2)

Guidance literature:

In ethanol; for 1h; Reflux;

Reference yield: 90.0%

(2RS)-1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(naphthalene-1-yloxy)propan-2-ol monohydrochloride (1164469-60-6,57149-08-3) → naftopidil (57149-07-2)

Guidance literature:

With water; sodium hydroxide; In toluene; Reagent/catalyst;

Reference yield:

1-(2-Methoxyphenyl)piperazine (35386-24-4) + α-naphthol (90-15-3) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → naftopidil (57149-07-2)

Guidance literature:

α-naphthol; epichlorohydrin; With potassium tert-butylate; In dimethyl sulfoxide; at 70 ℃; for 0.333333h; Flow reactor;

1-(2-Methoxyphenyl)piperazine; In dimethyl sulfoxide; at 140 ℃; for 0.333333h; under 5250.53 Torr; Flow reactor;

DOI:10.1039/c9gc01819k

upstream raw materials:

3-(1-naphthyloxy)-1,2-epoxypropane

1-(2-Methoxyphenyl)piperazine

α-naphthol

2-methoxy-phenylamine

Downstream raw materials:

O-desmethyl-naftopidil

(naphthyl)hydroxy-naftopidil

(phenyl)hydroxy-naftopidil

3-<4-(2-Methoxyphenyl)piperazinyl>-1,2-propandiol