Phenothiazine CAS 92-84-2
Introduction：Basic information about Phenothiazine CAS 92-84-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Phenothiazine Basic informationdescription Chemical Properties side effects Uses Synthesis
| Product Name: | Phenothiazine |
| Synonyms: | THIODIPHENYLAMINE;PHENOXUR;PHENOTHIAZINE;VERMITIN;10H-Phenothiazin;10H-Phenothiazine;Afi-Tiazin;Agrazine |
| CAS: | 92-84-2 |
| MF: | C12H9NS |
| MW: | 199.27 |
| EINECS: | 202-196-5 |
| Product Categories: | Organics;Benzoquinones, etc. (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Functional Materials;Charge Transport and Photosensitizing MaterialsBuilding Blocks;Heterocyclic Building Blocks;OLED and PLED Materials;Organic Electronics and Photonics;Thiazines;Building Blocks;Antibiotics;Chemical Structure;OthersAlphabetic;P;PER - POLA;Alphabetic;Heterocyclic Acids;Charge Transport and Photosensitizing Materials;Materials Science;OLED and PLED Materials;Organic and Printed Electronics;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;bc0001;92-84-2;A |
| Mol File: | 92-84-2.mol |
Phenothiazine Chemical Properties
| Melting point | 184 °C |
| Boiling point | 371 °C(lit.) |
| bulk density | 650kg/m3 |
| density | 1.362 |
| vapor pressure | 0.0000647 Pa (20 °C) |
| refractive index | 1.6353 |
| Fp | 202°C |
| storage temp. | Store below +30°C. |
| solubility | 0.127mg/l |
| pka | pKa 2.52 (Uncertain) |
| form | Prills or Beads |
| 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. |
| Major Application | cleaning products clinical cosmetics food and beverages forensics and toxicology personal care pharmaceutical (small molecule) |
| InChI | 1S/C12H9NS/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H |
| InChIKey | WJFKNYWRSNBZNX-UHFFFAOYSA-N |
| SMILES | N1c2ccccc2Sc3ccccc13 |
| LogP | 3.78 at 25℃ |
| CAS DataBase Reference | 92-84-2(CAS DataBase Reference) |
| NIST Chemistry Reference | Phenothiazine(92-84-2) |
| EPA Substance Registry System | Phenothiazine (92-84-2) |
Safety Information
| 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 |
| OEB | B |
| OEL | TWA: 5 mg/m3 [skin] |
| WGK Germany | 1 |
| RTECS | SN5075000 |
| F | 8-23 |
| Autoignition Temperature | 470 °C |
| TSCA | TSCA listed |
| HS Code | 29343090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 Skin Sens. 1 STOT RE 2 Oral |
| Hazardous Substances Data | 92-84-2(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
| 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:
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| Uses |
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| 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. 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 includingthe phenothiazine class of antipsychotics or neuroleptics.Phenothiazines are the largest class of neuroleptics andinclude agents such as chlorpromazine, thioridazine, andprochlorperazine. In 1933, a derivative of phenothiazine,promethazine, was synthesized. It was found to have muchmore significant sedative and antihistaminic effects thanprevious derivatives of phenothiazine and it was used toinduce sedation for surgical patients. After promethazine wasdeveloped, a series of agents, including chlorpromazine, wassynthesized and tested in France at a military hospital by theFrench physician Laborit. Laborit found that chlorpromazineinduced 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 aftera trial published in 1952 showed efficacy in treatment ofpsychosis in 38 individuals who received daily injections ofchlorpromazine. Chlorpromazine is the prototypical drug forthe phenothiazine class of antipsychotics. The phenothiazinesare classified as low-potency antipsychotics and have moreside effects at standard doses than the newer agents used asneuroleptics. For example, they are more anticholinergic andhave 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 ofreceptors including dopaminergic receptor sites. Phenothiazinesare used to treat psychosis including schizophrenia;violent, agitated, disturbed behavior; and mania secondary tobipolar disorder. Other uses include treatment of pain, headache,hiccups, acute severe anxiety, idiopathic dystonia,withdrawal, taste disorders, leishmaniasis, acute intermittentporphyria, and alleviation of nausea and vomiting.Phenothiazines allow smoother induction of anesthesia,potentiate anesthetic agents, and treat behavioral symptomssecondary to Alzheimer disease and senile dementia. Somephenothiazines exert an antipruritic effect and are useful forthe treatment of neurodermatitis and pruriginous eczema, andrelieve 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. |
| 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 andincludes 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 baseand the hydrochloride salt) that is a powder or waxy solid asa base and a crystalline powder as the hydrochloride. Chlorpromazineis odorless or has a slightly amine-like odor. It hasa melting point of 56–58 °C and in the basic form is practicallyinsoluble in water, soluble in alcohol, and less soluble in chloroformand ether. It is freely soluble in dilute mineral acids. Asthe hydrochloride salt, chlorpromazine is soluble in water, lesssoluble in alcohol and chloroform, and insoluble in ether. A10% 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 neurotransmissionby binding to dopamine (D1 and D2), muscarinic, histamine H1,and serotonergic 5-HT2 receptors. Phenothiazines also possessperipheral adrenergic receptor blockade and quinidine-likecardiac 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 | Benzene-->Sulfur-->Iodine-->Hexamethylenetetramine-->Diphenylamine |
| Preparation Products | Acrylamide-->Moricizine-->PTZ-343-->Promethazine hydrochloride-->3,7-dibromo-10H-phenothiazine-->3-bromo-10H-phenothiazine-->PROPYNAL-->10-Phenyl-10H-phenothiazine-->10-(propan-2-yl)-10H-phenothiazine |
