Norchlorpromazine

Base Information

• Chemical Name: Norchlorpromazine
• CAS No.: 1225-64-5
• Molecular Formula: C16H17 Cl N2 S
• Molecular Weight: 304.843
• Hs Code.: 2934300000
• UNII: O1G7LW1I5H
• DSSTox Substance ID: DTXSID50153631
• Nikkaji Number: J282.491D
• Wikidata: Q27216212
• Metabolomics Workbench ID: 87124
• ChEMBL ID: CHEMBL825
• Mol file: 1225-64-5.mol

Synonyms:N-desmethylchlorpromazine;N-monodesmethylchlorpromazine;norchlorpromazine;norchlorpromazine hydrochloride;norchlorpromazine maleate;norchlorpromazine monomaleate;norchlorpromazine perchlorate, ion(1+);norchlorpromazine, ion(1+)

Chemical Property of Norchlorpromazine

Chemical Property:

• Vapor Pressure: 1.4E-08mmHg at 25°C
• Boiling Point: 458.2°Cat760mmHg
• Flash Point: 230.9°C
• PSA: 40.57000
• Density: 1.229g/cm³
• LogP: 5.00810
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 304.0800974
• Heavy Atom Count: 20
• Complexity: 315

Purity/Quality:

99.0% Min ^*data from raw suppliers

Chlorpromazine impurity D European Pharmacopoeia (EP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCCN1C2=CC=CC=C2SC3=C1C=C(C=C3)Cl

Technology Process of Norchlorpromazine

There total 17 articles about Norchlorpromazine 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: 88.0%

2-chloro-N-(1-chloroethoxycarbonyl)-N-methyl-10H-phenothiazine-10-propanamine → Norchlorpromazine (1225-64-5)

Guidance literature:

In methanol; for 0.75h; Reflux;

DOI:10.1016/j.saa.2019.117652

Reference yield: 30.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-chloro-10-(3-aminopropyl)phenothiazine (2095-17-2) → Norchlorpromazine (1225-64-5)

Guidance literature:

formaldehyd; In methanol; at 20 ℃; for 0.25h;

2-chloro-10-(3-aminopropyl)phenothiazine; With methanol; sodium tetrahydroborate; at 80 ℃; for 0.666667h; Microwave irradiation;

DOI:10.1021/acschemneuro.8b00242

Reference yield: 11.0%

Chlorpromazine oxide (1672-76-0) → Norchlorpromazine (1225-64-5)

Guidance literature:

With ferrous(II) sulfate heptahydrate; In methanol; at 0 ℃; for 3h;

DOI:10.1039/c3md00387f

upstream raw materials:

methyl-3-chloropropylamine

2-chlorophenothiazine

N-[3-(2-chloro-phenothiazin-10-yl)-propyl]-formamide

2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine

Downstream raw materials:

3-(2-chlorophenothiazin-10-yl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylpropan-1-amine

3-(2-chlorophenothiazin-10-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylpropan-1-amine

N-[3-(2-chlorophenothiazin-10-yl)propyl]-2-(3,4-dimethoxyphenyl)-N-methylacetamide

3-(2-chloro-10H-phenothiazin-10-yl)-N-methyl-N-(4-(3-(piperidin-1-yl)propoxy)benzyl)-propan-1-amine

Refernces

• 1、 Limones-Herrero, Daniel,Palumbo, Fabrizio,Vendrell-Criado, Victoria,Andreu, Inmaculada,Lence, Emilio,González-Bello, Concepción,Miranda, Miguel A.,Jiménez, M. Consuelo. "Investigation of metabolite-protein interactions by transient absorption spectroscopy and in silico methods". . . Retrieved 2019/10/23.
• 2、 Uliassi, Elisa,Pena-Altamira, Luis Emiliano,Morales, Aixa V.,Massenzio, Francesca,Petralla, Sabrina,Rossi, Michele,Roberti, Marinella,Martinez Gonzalez, Loreto,Martinez, Ana,Monti, Barbara,Bolognesi, Maria Laura. "A Focused Library of Psychotropic Analogues with Neuroprotective and Neuroregenerative Potential". . p. 279 - 294. Retrieved 2018/10/20.