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    ChemicalBook >> CAS DataBase List >>Phenothiazine


    CAS No.
    Chemical Name:
    10H-Phenothiazine;THIODIPHENYLAMINE;XL-50;ent38;Feeno;Biverm;ENT 38;Orimon;Reconox;PHENOXUR
    Molecular Formula:
    Molecular Weight:
    MDL Number:
    MOL File:
    MSDS File:
    Last updated:2023-09-07 16:59:03

    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
    Exposure limits ACGIH: TWA 5 mg/m3 (Skin)
    NIOSH: TWA 5 mg/m3
    Stability Stable. Combustible. Incompatible with strong oxidizing agents, strong acids. May discolour upon exposure to light.
    LogP 3.78 at 25℃
    Indirect Additives used in Food Contact Substances PHENOTHIAZINE
    FDA 21 CFR 175.105; 176.170; 177.2600
    CAS DataBase Reference 92-84-2(CAS DataBase Reference)
    EWG's Food Scores 1-4
    NCI Dictionary of Cancer Terms phenothiazine
    NIST Chemistry Reference Phenothiazine(92-84-2)
    EPA Substance Registry System Phenothiazine (92-84-2)


    Risk and Safety Statements

    Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
    Signal word  Warning
    Hazard statements  H302-H317-H373-H410
    Precautionary statements  P260-P273-P280-P301+P312-P302+P352-P314
    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
    Autoignition Temperature 470 °C
    TSCA  Yes
    HS Code  29343090
    Toxicity LD50 orally in Rabbit: > 2000 mg/kg
    NFPA 704
    2 0

    Phenothiazine price More Price(40)

    Manufacturer Product number Product description CAS number Packaging Price Updated Buy
    Sigma-Aldrich 88580 Phenothiazine purum, ≥98.0% (GC) 92-84-2 1kg $105 2023-06-20 Buy
    Sigma-Aldrich 8.20975 Phenothiazine for synthesis 92-84-2 100g $29.6 2023-06-20 Buy
    Sigma-Aldrich 8.20975 Phenothiazine for synthesis 92-84-2 1kg $89.7 2023-06-20 Buy
    Sigma-Aldrich 8.20975 Phenothiazine for synthesis 92-84-2 50kg $1730 2023-06-20 Buy
    Sigma-Aldrich 1525707 Phenothiazine United States Pharmacopeia (USP) Reference Standard 92-84-2 500mg $400 2022-05-15 Buy
    Product number Packaging Price Buy
    88580 1kg $105 Buy
    8.20975 100g $29.6 Buy
    8.20975 1kg $89.7 Buy
    8.20975 50kg $1730 Buy
    1525707 500mg $400 Buy

    Phenothiazine Chemical Properties,Uses,Production


    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:

    • Chronic neurogenic pain (certain continuing pain conditions)
    • Huntington's chorea (hereditary movement disorder)
    • Migraine headaches


    • 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.


    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.


    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.


    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.


    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.


    Insecticide; manufacture of pharmaceuticals.


    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.

    Flammability and Explosibility

    Non flammable

    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 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.


    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.


    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.

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