Chlorpromazine

Base Information

• Chemical Name: Chlorpromazine
• CAS No.: 50-53-3
• Molecular Formula: C17H19 Cl N2 S
• Molecular Weight: 318.87
• Hs Code.: 2934999090
• European Community (EC) Number: 200-045-8
• NSC Number: 756689,167745
• UNII: U42B7VYA4P
• DSSTox Substance ID: DTXSID0022808
• Nikkaji Number: J2.794D
• Wikipedia: Chlorpromazine
• Wikidata: Q407972
• NCI Thesaurus Code: C367
• RXCUI: 2403
• Pharos Ligand ID: 49Q2DFBVD3KS
• Metabolomics Workbench ID: 42823
• ChEMBL ID: CHEMBL71
• Mol file: 50-53-3.mol

Synonyms:Aminazine;Chlorazine;Chlordelazine;Chlorpromazine;Chlorpromazine Hydrochloride;Contomin;Fenactil;Hydrochloride, Chlorpromazine;Largactil;Propaphenin;Thorazine

Chemical Property of Chlorpromazine

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 2.72E-08mmHg at 25°C
• Melting Point: 192 - 196 C (decomposes)
• Refractive Index: 1.6230 (estimate)
• Boiling Point: 450.1°Cat760mmHg
• PKA: pKa 9.3(H2O,t =24±1) (Uncertain)
• Flash Point: 226°C
• PSA: 31.78000
• Density: 1.212g/cm³
• LogP: 4.95940
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 318.0957475
• Heavy Atom Count: 21
• Complexity: 339

Purity/Quality:

99.9% ^*data from raw suppliers

Chlorpromazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 6.1 (Packing Group: III) UN NO.
• Hazard Codes: 6.1 (Packing Group: III) UN NO.

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Gastrointestinal Agents; Antipsychotic Agents
• Canonical SMILES: CN(C)CCCN1C2=CC=CC=C2SC3=C1C=C(C=C3)Cl
• Recent ClinicalTrials: Haloperidol With or Without Chlorpromazine in Treating Delirium in Patients With Advanced, Metastatic, or Recurrent Cancer
• Recent EU Clinical Trials: Cognitive effects of adjuntive Vortioxetine in early Schizophrenia
• Recent NIPH Clinical Trials: Valuable interaction with cognitive remediation and optimal antipsychotics for recovery in schizophrenia
• Description: This phenothiazine with sedative properties is used in human medicines and has induced contact dermatitis in nurses or in those working in the pharmaceutical industry. It is also used in veterinary medicine to avoid mortality of pigs during transportation. It is a sensitizer and a photosensitizer.
• Uses: In psychiatric practice, chlorpromazine is used in various conditions of psychomotor excitement in patients with schizophrenia, chronic paranoid and also manic-depressive conditions, neurosis, alcohol psychosis and neurosis accompanied by excitement, fear, stress, and insomnia. In comparison with other neuroleptics, chlorpromazine is unique in that it has an expressed sedative effect. It is sometimes used in anesthesiological practice for potentiating narcosis. It also has moderate anticonvulsant action. antiemetic, antipsychotic Chlorpromazine is approved by FDA for use in humans for the management of psychotic disorders (i.e., control of mania, treatment of schizophrenia); control of nausea and vomiting; relief of apprehension before surgery; acute intermittent porphyria; adjunctive treatment of tetanus; intractable hiccups; combativeness or explosive hyperexcitable behavior in children aged 1–12 years; and short-term treatment of hyperactivity in children with symptoms of impulsivity, difficulty sustaining attention, aggressiveness, mood lability, and poor frustration tolerance. Chlorpromazine is commonly used off-label for treatment of behavioral symptoms associated with dementia in the elderly and psychosis and agitation related to Alzheimer’s dementia; however, it carries a boxed warning regarding increased risk of death in patients with dementia-related psychosis. Chlorpromazine is also used off-label for managing agitation in terminal cancer patients, autonomic dysreflexia, cancer pain, adjunctive treatment of cholera, migraine headaches, opioid withdrawal, ocular pain, paralytic ileus, and phantom limb syndrome. In veterinary medicine, the use of chlorpromazine has been largely replaced by the phenothiazine acepromazine due to its more favorable pharmacokinetic profile. Chlorpromazine may be used as an antiemetic for small animals or for preoperative sedation. Chlorpromazine may also be used for management of hypertension in dogs and cats.

Technology Process of Chlorpromazine

There total 51 articles about Chlorpromazine 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: 85.0%

2-chlorophenothiazine (92-39-7) + 3-(dimethylamino)propyl chloride hydrochloride (5407-04-5) → 2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine (50-53-3)

Guidance literature:

With potassium hydroxide; at 80 ℃; for 2h;

DOI:10.1021/acs.joc.1c00403

Reference yield: 78.0%

C11H16ClIN2 (1219602-20-6) + o-bromothiophenol (6320-02-1) → 2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine (50-53-3)

Guidance literature:

With copper(l) iodide; potassium carbonate; L-proline; In ethyl methyl ether; at 90 - 110 ℃; Inert atmosphere;

DOI:10.1002/anie.200905646

Reference yield: 66.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-chloro-10-(3-aminopropyl)phenothiazine (2095-17-2) → 2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine (50-53-3)

Guidance literature:

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

DOI:10.1021/acschemneuro.8b00242

upstream raw materials:

2-chlorophenothiazine

3-(Dimethylamino)propyl chloride

3-Dimethylamino-1-propanol

2-chloro-phenothiazine-10-carbonyl chloride

Downstream raw materials:

dopaminoquinone

4-(2-Amino-1-hydroxy-ethyl)-[1,2]benzoquinone

adrenaline o-quinone

[3-(2-Chloro-phenothiazin-10-yl)-propyl]-dimethyl-(2-methyl-acryloyloxymethyl)-ammonium; chloride

Refernces

• 1、 Alfassi, Zeev B.,Mosseri, S.,Neta, P.. "Halogenated Alkylperoxyl Radicals as Oxidants: Effects of Solvents and of Substituents on Rates of Electron Transfer". . p. 3383 - 3385. Retrieved 1987.
• 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.
• 3、 Wisniewska, Joanna,Rzesnicki, Pawel,Topolski, Adrian. "A mechanistic study on the disproportionation and oxidative degradation of phenothiazine derivatives by manganese(III) complexes in phosphate acidic media". scheme or table. p. 767 - 774. Retrieved 2012/07/01.