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Phenothiazine

description Chemical Properties side effects Uses Synthesis
Phenothiazine
Phenothiazine structure
CAS No.
92-84-2
Chemical Name:
Phenothiazine
Synonyms
XL-50;ent38;Feeno;Biverm;ENT 38;Orimon;Reconox;PHENOXUR;VERMITIN;Agrazine
CBNumber:
CB2272320
Molecular Formula:
C12H9NS
Formula Weight:
199.27
MOL File:
92-84-2.mol

Phenothiazine Properties

Melting point:
184 °C
Boiling point:
371 °C(lit.)
Density 
1.362
vapor pressure 
0.0000647 Pa (20 °C)
refractive index 
1.6353
Flash point:
202°C
storage temp. 
Store below +30°C.
solubility 
0.127mg/l
form 
Prills or Beads
pka
pKa 2.52 (Uncertain)
color 
Yellow
PH
6 (10g/l, H2O, 20℃)(aqueous suspension)
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.
InChIKey
WJFKNYWRSNBZNX-UHFFFAOYSA-N
CAS DataBase Reference
92-84-2(CAS DataBase Reference)
Indirect Additives used in Food Contact Substances
PHENOTHIAZINE
FDA 21 CFR
175.105; 176.170; 177.2600
EWG's Food Scores
1-4
FDA UNII
GS9EX7QNU6
NCI Dictionary of Cancer Terms
phenothiazine
NIST Chemistry Reference
Phenothiazine(92-84-2)
EPA Substance Registry System
Phenothiazine (92-84-2)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS08
Signal word  Warning
Hazard statements  H319-H402-H302-H317-H373-H412
Precautionary statements  P261-P280a-P305+P351+P338-P321-P333+P313-P501a-P273-P280-P260-P301+P312+P330
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
8-23
Autoignition Temperature 470 °C
TSCA  Yes
HS Code  29343090
Toxicity LD50 orally in Rabbit: > 2000 mg/kg
NFPA 704
2
2 0

Phenothiazine price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.20975 Phenothiazine for synthesis 92-84-2 100 g $23.31 2021-03-22 Buy
Sigma-Aldrich 8.20975 Phenothiazine for synthesis 92-84-2 1 kg $70.39 2021-03-22 Buy
Sigma-Aldrich 88580 Phenothiazine purum, ≥98.0% (GC) 92-84-2 1kg $89.8 2021-03-22 Buy
Sigma-Aldrich 1525707 Phenothiazine United States Pharmacopeia (USP) Reference Standard 92-84-2 500mg $366 2021-03-22 Buy
Sigma-Aldrich 8.20975 Phenothiazine for synthesis 92-84-2 50 kg $1359.75 2021-03-22 Buy

Phenothiazine Chemical Properties,Uses,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.

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.

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:

Uses

Synthesis

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.

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.

Chemical Properties

yellow or pale green powder

Chemical Properties

Phenothiazine is a greenish-yellow to greenish-gray crystalline substance. Slight odor and taste.

Uses

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.

Uses

A key component of antipsychotic and antihistaminic drugs.

Uses

Employed in the preparation of carbazoles and piperazines,1 and charge-transfer semiconducting complexes.2

Uses

A rigid, tricyclic thiazine useful as an electron donor.

Uses

Insecticide; manufacture of pharmaceuticals.

Definition

ChEBI: The 10H-tautomer of phenothiazine.

brand name

Nemazine (Parke-Davis).

Synthesis Reference(s)

Synthesis, p. 506, 1974 DOI: 10.1055/s-1974-23359

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.

Safety Profile

Poison by intravenous route. Moderately toxic to humans by ingestion. Experimental reproductive effects. An insecticide. Large doses, i.e., heavy exposure, may cause hemolytic anemia and toxic degeneration of the liver. Can cause skin irritation and photosensitization. Dangerous; when heated to decomposition or on contact with acid or acid fumes it emits hghly toxic fumes of SOx and NOx.

Potential Exposure

Phenothiazine is used as an insecticide; as a base for the manufacture of tranquilizers; as anthelmintic in medicine and veterinary medicine; it is used widely as an intermediate in pharmaceutical manufacture; polymerization inhibitor, antioxidant.

Environmental Fate

Physicochemical Properties
Phenothiazine has the standard formula S(C6H4)2NH and includes a tricyclic structure that is related to the thiazines. Thiazines are used in the manufacture of synthetic dies.
Chlorpromazine
Chlorpromazine is a white to off-white substance (both the base and the hydrochloride salt) that is a powder or waxy solid as a base and a crystalline powder as the hydrochloride. Chlorpromazine is odorless or has a slightly amine-like odor. It has a melting point of 56–58 °C and in the basic form is practically insoluble in water, soluble in alcohol, and less soluble in chloroform and ether. It is freely soluble in dilute mineral acids. As the hydrochloride salt, chlorpromazine is soluble in water, less soluble in alcohol and chloroform, and insoluble in ether. A 10% aqueous solution has a pH of 3.5–4.5.

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Purification Methods

Crystallise it from *benzene, toluene, hexane or Me2CO (charcoal) after boiling for 10minutes under reflux. Filter the crystals off and dry them in an oven at 100o, then in a vacuum desiccator over paraffin chips. Also recrystallise it twice from water and dry it in an oven at 100o for 8-10hours. It sublimes at 130o/1mm and has UV with at 253nm in heptane. [Beilstein

Toxicity evaluation

Phenothiazines primarily block postsynaptic neurotransmission by binding to dopamine (D1 and D2), muscarinic, histamine H1, and serotonergic 5-HT2 receptors. Phenothiazines also possess peripheral adrenergic receptor blockade and quinidine-like cardiac effects. Phenothiazines may lower the seizure threshold.

Incompatibilities

Organosulfides are incompatible with strong acids and acid fumes; elevated temperatures; sulfur oxides and nitrogen oxides can be produced. Contact with strong reducing agents such as hydrides; azo and diazo compounds, halocarbons, isocyanates can generate heat and may form explosive hydrogen gas

Waste Disposal

Dissolve in combustible solvent and spray into incinerator equipped with afterburner and scrubber. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

Phenothiazine Preparation Products And Raw materials

Raw materials

Preparation Products


Phenothiazine Suppliers

Global( 421)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan Xiangtong Chemical Co., Ltd.
86-371-61312303
86-371-86017988 cathy@hnxtchem.com CHINA 293 58
Yangzhou Model Electronic Materials Co., Ltd.
+8613761402923
sales@modeltemol.com CHINA 440 58
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 21054 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8881 55
Guangzhou PI PI Biotech Inc
+8618371201331
020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 3001 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29968 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
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View Lastest Price from Phenothiazine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-08-25 Phenothiazine
92-84-2
US $5.00 / KG 1T AS COA 99% 100T Henan Xiangtong Chemical Co., Ltd.
2021-08-13 Phenothiazine
92-84-2
US $10.00 / KG 1KG 99% 10 mt Hebei Guanlang Biotechnology Co., Ltd.
2021-07-13 Phenothiazine
92-84-2
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

Phenothiazine Spectrum


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