Phenothiazine

Base Information

• Chemical Name: Phenothiazine
• CAS No.: 92-84-2
• Deprecated CAS: 8023-30-1,8048-22-4,8048-22-4
• Molecular Formula: C12H9NS
• Molecular Weight: 199.276
• Hs Code.: 29343090
• European Community (EC) Number: 202-196-5
• ICSC Number: 0937
• NSC Number: 760392,2037
• UNII: GS9EX7QNU6
• DSSTox Substance ID: DTXSID5021126
• Nikkaji Number: J3.932B
• Wikipedia: Phenothiazine
• Wikidata: Q410846
• NCI Thesaurus Code: C740
• Pharos Ligand ID: AK7774A7UJHV
• Metabolomics Workbench ID: 55729
• ChEMBL ID: CHEMBL828
• Mol file: 92-84-2.mol

Synonyms:phenosan;phenothiazine

Chemical Property of Phenothiazine

Chemical Property:

• Appearance/Colour: yellow or pale green powder
• Vapor Pressure: 1.06E-05mmHg at 25°C
• Melting Point: 184 °C
• Refractive Index: 1.6353
• Boiling Point: 371.003 °C at 760 mmHg
• PKA: pKa 2.52 (Uncertain)
• Flash Point: 178.176 °C
• PSA: 37.33000
• Density: 1.233 g/cm³
• LogP: 4.03280
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: 0.127mg/l
• Water Solubility.: 2 mg/L (25 ºC)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 199.04557046
• Heavy Atom Count: 14
• Complexity: 187

Purity/Quality:

99% ^*data from raw suppliers

Phenothiazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N,Xn
• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-43-51/53-36/38-40-20/21/22-52/53-48/22-22
• Safety Statements: 26-36-61-36/37/39-29-22-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: C1=CC=C2C(=C1)NC3=CC=CC=C3S2
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is mildly irritating to the skin.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged exposure may cause skin photosensitization. The substance when ingested may have effects on the blood and nervous system.
• description: Phenothiazine is a class of agents exhibiting antiemetic, antipsychotic, antihistaminic, and anticholinergic activities. Phenothiazines antagonize the dopamine D2-receptor in the chemoreceptor trigger zone (CTZ) of the brain, potentially preventing chemotherapy-induced emesis. In addition, these agents have peripherally or centrally antagonistic activity against alpha adrenergic, serotonergic, histaminic, and muscarinic receptors. Phenothiazines are used to treat serious mental and emotional disorders, including schizophrenia and other psychotic disorders. Some are used also to control agitation in certain patients, severe nausea and vomiting, severe hiccups, and moderate to severe pain in some hospitalized patients. Chlorpromazine is used also in the treatment of certain types of porphyria, and with other medicines in the treatment of tetanus. Phenothiazines may also be used for other conditions as determined by your doctor.
• Uses: Phenothiazine is a relatively widely used anthelmintic reagent with excellent efficacy in treating the Haemonchus contortus of cattle, horse and sheep, nodular worm, Bunostomum and Plasmodium chabaudi. Phenothiazine is the intermediates of fine chemicals such as dyes and drugs with itself being a auxiliary material for synthetic material (the anti-polymerization reagent for production of vinylon), fruit pesticides and veterinary anthelmintic. It is mainly used as the polymerization inhibitor for acrylic acid, acrylic esters, and methacrylic aicd as well as ester monomer. Phenothiazines are neuroleptic agents that affect a variety of receptors including dopaminergic receptor sites. Phenothiazines are used to treat psychosis including schizophrenia; violent, agitated, disturbed behavior; and mania secondary to bipolar disorder. Other uses include treatment of pain, headache, hiccups, acute severe anxiety, idiopathic dystonia, withdrawal, taste disorders, leishmaniasis, acute intermittent porphyria, and alleviation of nausea and vomiting. Phenothiazines allow smoother induction of anesthesia, potentiate anesthetic agents, and treat behavioral symptoms secondary to Alzheimer disease and senile dementia. Some phenothiazines exert an antipruritic effect and are useful for the treatment of neurodermatitis and pruriginous eczema, and relieve psychogenic itching. A key component of antipsychotic and antihistaminic drugs. Employed in the preparation of carbazoles and piperazines,1 and charge-transfer semiconducting complexes.2 A rigid, tricyclic thiazine useful as an electron donor. Insecticide; manufacture of pharmaceuticals.
• Description: Phenothiazine was initially synthesized in 1883 by Bernthsen. It was the basis for the development of other drugs including the phenothiazine class of antipsychotics or neuroleptics. Phenothiazines are the largest class of neuroleptics and include agents such as chlorpromazine, thioridazine, and prochlorperazine. In 1933, a derivative of phenothiazine, promethazine, was synthesized. It was found to have much more significant sedative and antihistaminic effects than previous derivatives of phenothiazine and it was used to induce sedation for surgical patients. After promethazine was developed, a series of agents, including chlorpromazine, was synthesized and tested in France at a military hospital by the French physician Laborit. Laborit found that chlorpromazine induced calm in patients and had other effects that might be useful clinically. Chlorpromazine, known colloquially as ‘Laborit’s drug’ was released into the market in 1953 after a trial published in 1952 showed efficacy in treatment of psychosis in 38 individuals who received daily injections of chlorpromazine. Chlorpromazine is the prototypical drug for the phenothiazine class of antipsychotics. The phenothiazines are classified as low-potency antipsychotics and have more side effects at standard doses than the newer agents used as neuroleptics. For example, they are more anticholinergic and have more extrapyramidal effect than newer agents.

Technology Process of Phenothiazine

There total 108 articles about Phenothiazine 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: 95.0%

10-(1-methoxy-2-propynyl)phenothiazine → Propargylic aldehyde (624-67-9) + 10H-phenothiazine (92-84-2)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; at 18 ℃;

DOI:10.1023/A:1012341921034

Reference yield: 95.0%

10-acetyl-10H-phenothiazine (1628-29-1) → 10H-phenothiazine (92-84-2)

Guidance literature:

With potassium tert-butylate; In ethyl acetate; at 20 ℃; for 2h;

DOI:10.1021/acs.joc.1c00403

Reference yield: 94.0%

1-Bromo-2-iodobenzene (583-55-1) + 2-amino-benzenethiol (137-07-5) → 10H-phenothiazine (92-84-2)

Guidance literature:

1-Bromo-2-iodobenzene; 2-amino-benzenethiol; With ferric citrate; In N,N-dimethyl-formamide; at 80 ℃; for 2h; Green chemistry;

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 1h; regioselective reaction; Green chemistry;

DOI:10.2174/1570178615666180806114523

upstream raw materials:

2-(phenylamino)benzoic acid

bis-(2-nitro-phenyl)-sulfide

(2-aminophenyl)-2’-bromophenyl sulfide

diphenylamine hydrochloride

Downstream raw materials:

2-methyl-4-(2,6,6-trimethyl-cyclohex-2-enyl)-crotonaldehyde

10-(3-pyrrolidin-1-yl-propyl)-10H-phenothiazine

Perazin

4-oxo-4-phenothiazin-10-yl-butyric acid

Refernces

• 1、 Li, Wei,Wan, Xiaobo,Zeng, Fanqi,Xie, Yuting,Wang, Yanli,Zhang, Wei,Li, Li,Huang, Niu. "More than just a GPCR ligand: Structure-based discovery of thioridazine derivatives as Pim-1 kinase inhibitors". . p. 507 - 511. Retrieved 2014.
• 2、 Levitskiy, Oleg A.,Dulov, Dmitry A.,Bogdanov, Alexey V.,Magdesieva, Tatiana V.. "Carbon- and SO2-Locked Diarylnitroxides: Quantum Chemical Consideration, Synthesis, and Electrochemistry". . p. 6225 - 6231. Retrieved 2019.
• 3、 Svyatkina, L. I.,Kurov, G. N.,Skvortsova, G. G.. "VINYLATION OF ALCOHOLS BY 10-VINYLPHENOTHIAZINE". . p. 1947 - 1950. Retrieved 1985.
• 4、 Rui, Xiyan,Wang, Chao,Si, Dongjuan,Hui, Xuechao,Li, Keting,Wen, Hongmei,Li, Wei,Liu, Jian. "One-Pot Tandem Access to Phenothiazine Derivatives from Acetanilide and 2-Bromothiophenol via Rhodium-Catalyzed C-H Thiolation and Copper-Catalyzed C-N Amination". . p. 6622 - 6632. Retrieved 2021/05/29.
• 5、 Li, Jinshan,Wang, Jiali,Yang, Jianguo,Yao, Wubing,Zhong, Aiguo. "Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores". . p. 8086 - 8090. Retrieved 2020/11/03.