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Phenothiazine

description Physical-Chemical properties of phenothiazine and its role Chemical Properties Phenothiazines side effects Uses Biological Activity Preparation of phenothiazine Production method Category Toxicity grading Acute toxicity Flammability and hazardous characteristics Storage characteristics Extinguishing agent Professional Standards

CAS No.92-84-2
Chemical Name:Phenothiazine
Synonyms:ent38;Feeno;XL-50;Biverm;ENT 38;Orimon;Reconox;PHENOXUR;VERMITIN;Antiverm
CBNumber:CB2272320
Molecular Formula:C12H9NS
Formula Weight:199.27
MOL File:92-84-2.mol
Phenothiazine Property
Melting point : 184 °C
Boiling point : 371 °C(lit.)
density : 1.362
refractive index : 1.6353
Fp : 202°C
Water Solubility : 2 mg/L (25 ºC)
Sensitive : Light Sensitive
Merck : 14,7252
BRN : 143237
Stability:: Stable. Combustible. Incompatible with strong oxidizing agents, strong acids. May discolour upon exposure to light.
CAS DataBase Reference: 92-84-2(CAS DataBase Reference)
NIST Chemistry Reference: Phenothiazine(92-84-2)
EPA Substance Registry System: 10H-Phenothiazine(92-84-2)
Safety
Hazard Codes : Xi,N,Xn
Risk 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
WGK Germany : 1
RTECS : SN5075000
F : 8-23
TSCA : Yes
HS Code : 29343090
Hazardous Substances Data: 92-84-2(Hazardous Substances Data)

Phenothiazine Chemical Properties,Usage,Production

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.
Physical-Chemical properties of phenothiazine and its role
Phenothiazine is a kind of organic aromatic compound consisting of two benzene rings (the core of phenothiazine) connecting by sulfur and nitrogen atom with the compound recrystallized from ethanol or benzene being orthorhombic yellow or gray-green prismatic crystals and the compound precipitated from toluene or butanol being yellow leaf-shaped crystals which can be evaporated together with the steam. It has a relative molecular mass of 199.28, the melting point of 186~189 ℃, the boiling point of 371 ℃ and the sublimation point being 290 ℃ (5.333 × 103Pa), 130 ℃ (0.133 × 103Pa). It is insoluble in water, petroleum ether and chloroform, slightly soluble in ethanol and mineral oil, soluble in ether and acetone and easily soluble in benzene and hot acetic acid. Its solubility of 25 ℃ (g/100g) is as below: Acetone: 25.40, ethanol: 3.40; benzene: 32.0. Under the exposure to sunshine and air, it becomes darker in color and can be supplemented with 0.3% of methylamine as protection reagent for storage. When there are impurities, its color can also become dark. When coming across acid and acid vapor, it can be subject to decomposition and produces toxic nitrogen oxides and sulfur dioxide gas. Phenothiazine can be subject to sublimation with faint smell and irritation effect on the skin. It can cause rash as well as visceral disorders through percutaneous absorption. Rat via oral administration has a LD50 of 5000mg/kg. The maximal allowable concentration in the workplace is 5 mg/m3. Laboratory can directly make it through heating diphenylamine with sulfur at the same time to until no hydrogen sulfide gas was released. Phenothiazine can be used as the intermediate for the manufacturing of methylene blue dye as well being used for manufacturing an important class of tranquilizers and anti-histamine drugs such as chlorpromazine, perphenazine, thioridazine and promethazine, etc. Furthermore, phenothiazine can also be used as a polymerization inhibitor of vinyl acetate, raw material of the rubber antioxidant, synthetic dyes, pharmaceuticals, fruit pesticides and animal anthelmintic agents.
The above information is edited by the chemicalbook of Dai Xiongfeng.
Chemical Properties
It is clean gray-green powder with the melting point of 185.5 ℃, boiling point of 371 ℃, 290 ℃ (5.33kPa). It is insoluble in petroleum ether, chloroform and water, and soluble in ether and hot acetic acid. It will be oxidized upon exposure to light in the air.
Phenothiazines
Phenothiazine itself is a veterinary anthelmintic, but the name is also used to denote a group of major tranquillisers resembling phenothiazine in molecular structure.
Phenothiazines were the first effective neuroleptics to be introduced and they are still commonly used.
Chemical structure common to phenothiazines
Chemical structure common to phenothiazines
The phenothiazines are the largest chemical group, comprising more than 40 compounds (only the most relevant are listed below) grouped under three subtypes.Drugs in this group share the same three-ring structure with different side chains joined at the nitrogen atom of the middle ring. The activity of the group can be affected by substitutions at position 2 or 10. The phenothiazines are categorized into three subclasses based on substitutions at position 10: aliphatic, piperidine, and piperazine phenothiazines.
Aliphatic (a sedative neuroleptic)
  • Chlorpromazine
  • Levomepromazine
  • Promazine
  • Triflupromazine
Piperidine (a less sedating preparation)
  • Mesoridazine
  • Pericyazine
  • Pipotiazine
  • Thioridazine
Piperazine (a long acting derivative for maintenance treatment)
  • Perphenazine
  • Fluphenazine
  • Trifluoperazine
side effects
For more than a decade, phenothiazine drugs have been used to treat a variety of disorders and have proved particularly effective in the treatment of schizophrenia. Clinical experience indicates that initial extremely high dosages are necessary to effect improvement of patients with schizophrenic illnesses.

During 1964, several sequelae have been reported following prolonged high dosage of these drugs. These recent reports refer to side effects which are apparently permanent, in contrast to earlier communications of transient deleterious effects. For example, it has been known for several years that extrapyramidal disorders occur frequently in patients taking phenothiazines; however, a reduction in dosage or cessation of medication appeared to produce a return to the normal state.

Phenothiazines may cause unwanted, unattractive, and uncontrolled face or body movements that may not go away when you stop taking the medicine. They may also cause other serious unwanted effects. You and your doctor should talk about the good this medicine will do as well as the risks of using it. Also, your doctor should look for early signs of these effects at regular visits. Your doctor may be able to stop or decrease some unwanted effects, if they do occur, by changing your dose or by making other changes in your treatment.

These medicines are available only with your doctor's prescription.

Levoprome(R) (methotrimeprazine) is no longer available in the United States. At the end of May 1998, Immunex Corporation stopped marketing it.

Once a medicine has been approved for marketing for a certain use, experience may show that it also is useful for other medical problems. Although these uses are not included in product labeling, phenothiazines are used in certain patients with the following medical conditions:
  • Chronic neurogenic pain (certain continuing pain conditions)
  • Huntington's chorea (hereditary movement disorder)
  • Migraine headaches
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.
Biological Activity
Description
Phenothiazine is a dopamine-2 (D2) receptor antagonist therefore decreases the effect of dopamine in the brain.
Targets
D2 receptor
In vitro
Phenothiazines mostly substitutes at position 10 with the dialkylaminoalkyl groups and additionally at position 2 with small groups exhibit valuable activities such as neuroleptic, antiemetic, antihistaminic, antipuritic, analgesic and antihelmintic. 2-trifluoromethyl-10-(4-aminobutyl)phenothiazine inhibits S. cerevisiae strains and T. mentagrophites with MIC of 0.4 μg/mL and 1.5 μg/mL, respectively. 10-carbamoylalkylphenothiazines shows significant activities against Gram-positive Bacillus subtilis with MIC’s in the range of 7.8 μg/mL–30 μg/mL. The tetracyclic phenothiazines (modified with the naphthoquinone ring) shows significant actibacterial activity against S. aureus with the MIC50 of 12.5 μg/mL. Phenothiazines with the butylene linker are more effective than with the propylene linker, the 2-chloro-10-chloroethylureidobutyl derivative giving GI50 of 1.4 μM and 1.6 μM against 4 leukemia cell lines and 7 colon cancer cell lines. 10-Amino(hydroxy)propylphenothiazines (5 μM) induces a marked G2/M phase of cell-cycle arrest followed by cell death in human transformed WI38VA cells after 2-day incubation.
Phenothiazine drugs undergo extensive metabolism in the body before being excreted, mainly ring hydroxylation, ring sulphoxidation, N-demethylation, N-oxidation, sulphate and glucuronide conjugation. Phenothiazines have considerably lower binding affinities to α2-adrenoceptors than to dopamine D2 receptors and al-adrenoceptors.
Phenothiazines have significant in vitro activity against susceptible, polydrug-and multidrug-resistant strains of M. tuberculosis, as well as enhancing the activity of some agents employed for first-line treatment.
References
http://www.ncbi.nlm.nih.gov/pubmed/21620536
http://www.ncbi.nlm.nih.gov/pubmed/11328759
Preparation of phenothiazine
22 g of diphenylamine, 8.2 g of sulfur, and 3.2 gms. of anhydrous aluminum chloride are melted together. The reaction sets 140-150° C with the rapid evolution of hydrogen sulfide; by lowerg the temperature, a few degrees the reaction can be slackened. Wen the reaction has moderated, the temperature is raised to 160° C for a time. The melt, when cool, is ground up and extracted, first with water and then with dilute alcohol. The residue consists of almost pure phenothiazine. It can be recrystallised from alcohol. Yield 93%, yellowish leaflets; m.p. 180° C.
Preparation of phenothiazine
Systematic organic chemistry, by W. M. Cumming, 325-326, 1937.
Production method
Take Diphenylamine as raw material, and then have vulcanization with the catalysis of iodine to obtain it.
Diphenylamine, iodine and sulfur were mixed and heated to 200 ℃ for reaction of 2h, then heated with superheated steam directly to 220-250 ℃. After the reaction mass is separated from the water, use the mixture solution of ethanol and hexamine (mass ratio of 1.5: 1) to wash; further dry and pulverized to obtain the final product.
Category
Pesticide
Toxicity grading
Poisoning
Acute toxicity
Oral-mouse LD50: 5000 mg/kg; Intravenous-Mouse LD50: 178 mg/kg.
Flammability and hazardous characteristics
It is combustible with combustion producing toxic sulfur oxide and nitrogen oxide gases.
Storage characteristics
Treasury: ventilation low-temperature and dry; store and transport it separately from oxidant.
Extinguishing agent
Dry powder, foam, sand.
Professional Standards
TLV-TWA 5 mg/m³; STEL 10 mg/m.
Chemical Properties
yellow or pale green powder
Usage
A key component of antipsychotic and antihistaminic drugs.
Usage
Employed in the preparation of carbazoles and piperazines,1 and charge-transfer semiconducting complexes.2
Definition
ChEBI: The 10H-tautomer of phenothiazine.
General Description
Light green to steel-blue powder. Acquires a greenish-brown tint under exposure to sunlight.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Phenothiazine is slowly decomposed by sunlight. . Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.
Fire Hazard
Flash point data for Phenothiazine are not available, but Phenothiazine is probably combustible.
Phenothiazine Preparation Products And Raw materials
Raw materials
Sulfur Benzene Iodine Diphenylamine Hexamethylenetetramine
Preparation Products
SODIUM PHENOTHIAZINE-10-YL-PROPYLSULFONATE Promethazine hydrochloride CARBAMIC ACID, [10-[3-(4-MORPHOLINYL)-1-OXOPROPYL]-10H-PHENOTHIAZIN-2-YL]-, ETHYL ESTER Acrylamide
Phenothiazine Suppliers      Global( 248)Suppliers     
SupplierTelFaxEmailCountryProdListAdvantage
Shanghai TongYuan Chemical Co., Ltd. 021-69182866 69186366021-69182022tongyuanchem@126.comChina 5184 58
Shanghai LanRun Chemical Co., Ltd. 021-69515658 ; 69515628021-69515998longrunchem@163.comChina 5966 50
Shanghai XiZhi Chemical Co., Ltd. 021-69005855021-69005955xizhichem@163.comChina 4254 55
Shanghai Xilong Biochemical Technology Co., Ltd. 021-52907766-8042021-52906523order@drmaolab.comChina 10070 58
J & K SCIENTIFIC LTD. 400-666-7788 +86-10-82848833+86-10-82849933jkinfo@jkchemical.com;market6@jkchemical.comChina 96832 76
Meryer (Shanghai) Chemical Technology Co., Ltd. +86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-59487313(Beijing)+86-(0)21-61259102(Shanghai) +86-(0)755-86170066(ShenZhen) +86-(0)10-88580358(Beijing)sh@meryer.comChina 40403 62
3B Pharmachem (Wuhan) International Co.,Ltd. 86-21-50328103 * 801、802、803、804 Mobile:1893055203786-21-503281093bsc@sina.comChina 15950 69
future industrial shanghai co., ltd 021-61552785,400-0066-400021-55660885sales@jonln.comChina 2091 65
Alfa Aesar 400-610-6006; 021-67582000021-67582001/03/05saleschina@alfa-asia.comChina 30315 84
TCI (Shanghai) Development Co., Ltd. 800-988-0390021-67121385sales@tcishanghai.com.cnChina 22833 81
 
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