Promazine

Base Information

• Chemical Name: Promazine
• CAS No.: 58-40-2
• Molecular Formula: C17H20 N2 S
• Molecular Weight: 284.425
• European Community (EC) Number: 200-382-0
• NSC Number: 31447
• UNII: O9M39HTM5W
• DSSTox Substance ID: DTXSID2023517
• Nikkaji Number: J2.805C
• Wikipedia: Promazine
• Wikidata: Q419822
• NCI Thesaurus Code: C61908
• Pharos Ligand ID: YA526ZDT64KV
• Metabolomics Workbench ID: 42780
• ChEMBL ID: CHEMBL564
• Mol file: 58-40-2.mol

Synonyms:Phenothiazine,10-[3-(dimethylamino)propyl]- (8CI); 10-[3-(Dimethylamino)propyl]phenothiazine;3276RP; A 145; Ampazine; Berophen; Esparin;N-(3-Dimethylaminopropyl)phenothiazine; NSC 31447; Neo-Hibernex; Prazin;Prazine; Promazine; Protactyl; RP 3276; Romtiazin; Sinophenin; Tomil; Verophen;Wy 1094

Chemical Property of Promazine

Chemical Property:

• Melting Point: 25°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 412.7°Cat760mmHg
• PKA: pKa 9.4(H2O,t =24±1) (Uncertain)
• Flash Point: 203.4°C
• PSA: 31.78000
• Density: 1.133g/cm³
• LogP: 4.30600
• Water Solubility.: 14.22mg/L(24 oC)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 284.13471982
• Heavy Atom Count: 20
• Complexity: 285

Purity/Quality:

99%, ^*data from raw suppliers

N,N-DIMETHYL-3-PHENOTHIAZIN-10-YL-PROPAN-1-AMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCCN1C2=CC=CC=C2SC3=CC=CC=C31
• Uses: ntipsychotic. In psychiatric practice, promazine is used in minor cases of psychomotor excitement in schizophrenics, in paranoid and manic-depressive conditions, for neurosis, alcoholic psychosis, and others. It is sometimes used in anesthesiological practice. Promazine is an antipsychotic and a tranquilizer.

Technology Process of Promazine

There total 17 articles about Promazine 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: 82.0%

10H-phenothiazine (92-84-2) + 3-(dimethylamino)propyl chloride hydrochloride (5407-04-5) → promazine (58-40-2)

Guidance literature:

10H-phenothiazine; With n-butyllithium; In hexane; toluene; at -78 ℃; for 1h; Inert atmosphere;

3-(dimethylamino)propyl chloride hydrochloride; With n-butyllithium; triisobutylaluminum; In hexane; toluene; Reflux; Inert atmosphere;

DOI:10.1016/j.ejmech.2017.09.021

Reference yield: 74.0%

1-Bromo-2-iodobenzene (583-55-1) + o-bromothiophenol (6320-02-1) + 1-amino-3-(dimethylamino)propane (109-55-7) → promazine (58-40-2)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; In toluene; at 60 - 160 ℃; for 2.33333h; Microwave irradiation;

DOI:10.1002/anie.200705209

Reference yield: 74.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-(10H-phenothiazin-10-yl)propan-1-amine (2095-21-8) → promazine (58-40-2)

Guidance literature:

With formic acid; In water; at 80 ℃; for 8h; Microwave irradiation;

DOI:10.1021/acschemneuro.8b00242

upstream raw materials:

p-toluenesulfonic acid 3-dimethylamino-n-propyl ester

10H-phenothiazine

3-(Dimethylamino)propyl chloride

formaldehyd

Downstream raw materials:

N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-3-phenothiazin-10-ylpropan-1-amine

N-methyl-10H-phenothiazine-10-propanamine hydrochloride

10H-phenothiazine-10-carbaldehyde

10H-phenothiazine

Refernces

• 1、 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.
• 2、 Hayashi, Hideki,Koizumi, Take-Aki. "Preparation and electrochemical behavior of N-substituted phenothiazine oxide". . p. 1441 - 1449. Retrieved 2016/08/10.