페노티아진

Phenothiazine

HCID 7108CAS 92-84-2

기본 정보

표준 SMILES
c1ccc2c(c1)Nc1ccccc1S2
InChIKey
WJFKNYWRSNBZNX-UHFFFAOYSA-N
분자식
C12H9NS
평균 분자량
199.27 g/mol
단동위원소 질량
199.04557046

이름 및 식별자

우선 이름
Phenothiazine
IUPAC
10H-phenothiazine
현지명
페노티아진
영어명
Phenothiazine
분자식
C12H9NS
분자량
199.27

이름 및 동의어

PHENOTHIAZINE10H-Phenothiazine92-84-2ThiodiphenylamineDibenzothiazineContavermDibenzo-1,4-thiazineFenovermNemazinePhenosanFeenoPhenthiazine
이름 더 보기
페노티아진티오디페닐아민페노티아진및그화합물10H-페노티아진10H-페놀싸이아진다이벤조-1,4-싸이아진다이벤조-1,4-티아진다이벤조싸이아진다이벤조티아진싸이오다이페닐아민티오다이페닐아민페놀싸이아진XL-50ent38BivermENT 38OrimonReconoxPHENOXUR
AntivermFentiazinHelmetinaLethelminPadophenePhenegicPhenovermPhenovis

데이터베이스 식별자

CAS
92-84-2
PubChem CID
7108
DTXSID
DTXSID5021126
ChEMBL
CHEMBL828
ChEBI
CHEBI:37931
UNII
GS9EX7QNU6
EC Number
202-196-5
Nikkaji
J3.932B

물성

구조 계산 물성

XLogP
4.2
극성 표면적
37.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
14

실험 및 물리화학적 성질

LogP · 2건

log Kow = 4.15

4.15

OdorSLIGHT ODOR
TasteTASTELESS
Density1.34 g/cm³
Color/Form · 4건

YELLOW, RHOMBIC LEAFLETS OR DIAMOND-SHAPED PLATES FROM TOLUENE OR BUTANOL

YELLOW PRISMS FROM ALCOHOL

GRAYISH-GREEN TO GREENISH YELLOW POWDER, GRANULES OR FLAKES

Grayish-green to greenish-yellow solid. [insecticide]

Solubility · 6건

less than 1 mg/mL at 68 °F (NTP, 1992)

FREELY SOL IN BENZENE; SOL IN ETHER & IN HOT ACETIC ACID; SLIGHTLY SOL IN ALCOHOL & IN MINERAL OILS; PRACTICALLY INSOL IN PETROLEUM ETHER, CHLOROFORM

VERY SOL IN ACETONE

Water solubilty = 1.59 mg/l at 25 °C

Solubility in water: none

Insoluble

물리화학적 성질

녹는점
184 °C · 184 °C
끓는 점
371 °C · 371 °C(lit.)
밀도
1.362 · 1.362
증기압
0.0000647 Pa · 0.0000647 Pa (20 °C)
굴절률
1.6353 · 1.6353
인화점
202 °C · 202°C

화학적 성질

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

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 0.7% (24 of 3466) of reports.

Warning

H302 (94.2%): Harmful if swallowed [Warning Acute toxicity, oral];H317 (97.4%): May cause an allergic skin reaction [Warning Sensitization, Skin];H373 (93.9%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure];H400 (11.9%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (11.9%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard];H412 (83.2%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P260, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P319, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3466 reports by companies from 53 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 24 of 3466 reports by companies.;There are 52 notifications provided by 3442 of 3466 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

유해성 정보

Regulatory Information · 4건

Chemical: 10H-Phenothiazine

10H-Phenothiazine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 10H-Phenothiazine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 19-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14459;Status: Active Update: 15-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/34074

Phenothiazine: Does not have an individual approval but may be used under an appropriate group standard

Fire Hazards · 2건

Flash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialALTHOUGH PHENOTHIAZINE OXIDIZES FAIRLY EASILY WHEN IT IS EXPOSED TO AIR, RISK OF FIRE IS NOT HIGH.
Health Hazards · 1건

Excerpt from NIOSH Pocket Guide for Phenothiazine:;Exposure Routes: Inhalation, skin absorption, ingestion, skin and/or eye contact;Symptoms: Itching, irritation, reddening skin; hepatitis, hemolytic anemia, abdominal cramps, tachycardia; kidney damage; skin photophobia (abnormal visual intolerance to light) sensitization;Target Organs: Skin, cardiovascular system, liver, kidneys (NIOSH, 2024)

Hazards SummaryA cause of photoallergic contact dermatitis; [ICSC] Phenothiazine may cause liver injury when taken by mouth as a drug. [ACGIH]
FDA RequirementsPhenothiazine for use only as a polymerization-control agent is an indirect food additive for use as a component of adhesives.

안전 및 보호

Fire Fighting · 2건

Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use powder, water spray, foam, carbon dioxide.

First Aid Measures · 4건

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention if skin irritation occurs.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Seek medical attention if you feel unwell.

First Aid · 2건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Soap wash promptly - If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageSeparated from strong oxidants and strong acids. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Nonfire Spill Response · 1건

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should store this compound under refrigerated conditions and protect it from exposure to light. (NTP, 1992)

Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

독성 정보

Interactions · 2건

PREVIOUS DRENCHING WITH CARBON TETRACHLORIDE MAY ALSO SERVE TO INCR ITS TOXICITY.

ANTIOXIDANTS, EG PHENOTHIAZINE, INHIBITED THE MUTAGENICITY OF BENZO(A)PYRENE & SOME OF ITS DERIVATIVES TOWARDS SALMONELLA TYPHIMURIUM STRAIN TA98; THIS INHIBITION WAS CONCN DEPENDENT.

Target OrgansSkin, cardiovascular system, liver, kidneys
Environmental Fate · 3건

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4300(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that phenothiazine will have slight mobility in soil(SRC). Volatilization of phenothiazine will not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.8X10-8 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 8.9X10-7 mm Hg(5,SRC). The adsorptivity of phenothiazine is expected to be sensitive to pH since phenothiazine is a base with a pKa of 2.52(6). According to a MITI biodegradation study(7), biodegradation of phenothiazine will not be an important fate process in soil(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4300(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that phenothiazine would adsorb to suspended solids and sediment(SRC). Phenothiazine would be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 2.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4,SRC). Experimental BCF values of 127-660 and 180-528(6) suggest that phenothiazine will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5). According to a MITI biodegradation study(6), biodegradation of phenothiazine will not be an important fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenothiazine, which has an estimated vapor pressure of 8.9X10-7 mm Hg at 25 °C(2,SRC) will exist as both vapor and particulate in the ambient atmosphere. Vapor-phase phenothiazine is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 2 hours(3,SRC). Particulate-phase phenothiazine may be physically removed from the air by dry deposition(SRC).

Adverse Effects · 2건

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Dermatotoxin - PACD (photoallergic contact dermatitis).;ACGIH Carcinogen - Not Classifiable.

The most common adverse reactions include:;* Extrapyramidal symptoms, including dystonia, parkinsonism, akathisia, and tardive dyskinesia.;* Weight gain;* Orthostatic hypotension can manifest in 75% of patients with potentially increased risk due to diabetes and pre-existing cardiovascular disorders.;* QTc prolongation;* Pseudoparkinsonism most often occurring in women or older patients.;* Seizures;* Delirium;* Psychosis;Rare adverse events:;* Neuroleptic malignant syndrome;* Retinitis pigmentosa;* Cataracts;* Dermatological allergic reactions;* Poikilothermia;* Agranulocytosis;Common less severe adverse events:;* Urinary hesitancy and retention;* Dry mouth,;* Dry eyes

Exposure Routes · 2건

The substance can be absorbed into the body by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Toxicity Summary · 1건

A review of 48 hospital-admitted phenothiazine toxicities with concentrations of 200 mg to 500 mg per patient has listed common reactions such as hypothermia, tachycardia, tachypnea, and decreased diastolic blood pressure. A tendency towards obtundation can present in cases where other drugs were also involved. Furthermore, a pupil size of less than 3 mm was present in the most severe poisoning cases. Prolonged QTc interval was noted, and patients were treated with diphenylhydantoin. An echocardiogram is a suggested approach for all cases of phenothiazine overdoses.;Treatment methods for phenothiazine overdoses included administering ipecac, gastric lavage, intravenous diphenhydramine, and intravenous hydration to reverse extrapyramidal symptoms and absorption. No fatalities occurred, and 50% of the patients were discharged following 24 hours, while the other 50% stayed for an average duration of 3.4 days. Potentially serious complications were present in 71% of the patients who stayed longer than 24 hours; however, all of those patients recovered.

규제 정보

Regulatory Information · 4건

Chemical: 10H-Phenothiazine

10H-Phenothiazine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 10H-Phenothiazine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 19-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14459;Status: Active Update: 15-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/34074

Phenothiazine: Does not have an individual approval but may be used under an appropriate group standard

FDA RequirementsPhenothiazine for use only as a polymerization-control agent is an indirect food additive for use as a component of adhesives.
TSCA Requirements · 1건

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Phenothiazine is included on this list.

FIFRA Requirements · 1건

While petitions for tolerances for negligible residues are pending and until action is completed on the petitions, an interim tolerance of 2 ppm is established for residues of phenothiazine in or on the following raw agricultural commodity(ies): meat, fat, and meat byproducts of cattle.

안전 데이터

OEB
B
OEL
TWA: 5 mg/m3 [skin]
wgk
1
tsca
TSCA listed
rtecs
SN5075000
독성
LD50 orally in Rabbit: > 2000 mg/kg

화학 및 산업

약리 정보

Metabolism/Metabolites · 4건

SOME PHENOTHIAZINE IS CONVERTED WITHIN GUT TO SOL DERIV, MAINLY PHENOTHIAZINE SULFATE...

YIELDS 3-HYDROXYPHENOTHIAZINE IN DOGS. /FROM TABLE/

THE ANTHELMINTIC, PHENOTHIAZINE, WAS OXIDIZED TO SULFOXIDE BY ENZYMES OF THE PROGLOTTIDS OF THE CESTODE, MONIEZIA EXPANSA & CYTOSOL OF INTESTINAL EPITHELIAL CELLS OF THE NEMATODE ASCARIS SUUM. ENZYMES IN THESE TISSUES ALSO DECR SULFOXIDES TO THIOETHERS IN ABSENCE OF O.

RAT, MOUSE, & GERBIL EXCRETED THE MAJORITY OF PHENOTHIAZINE IN CONJUGATED FORM. THE RAT, MOUSE, & GERBIL PRODUCED LEUCOPHENOTHIAZONE SULFATE AS MAJOR METABOLITE, RELYING MORE ON C-OXIDATION PATHS THAN THE HAMSTER WHICH EXCRETED LARGE AMT OF PHENOTHIAZINE N-GLUCURONIDE.

MeSH Pharmacological ClassificationSubstances that are destructive to protozoans.
Absorption, Distribution and Excretion · 5건

BECAUSE OF ITS LOW SOLUBILITY, RATE OF ITS ABSORPTION FROM GI TRACT IS DEPENDENT ON PARTICLE SIZE. MICRONIZED FORM OF DRUG IS ABSORBED RAPIDLY.

...ABOUT 30-50% OF ORAL DOSE PASSES THROUGH ALIMENTARY TRACT UNCHANGED. SOME PHENOTHIAZINE IS CONVERTED WITHIN GUT TO SOL DERIV...WHICH ARE ABSORBED INTO PORTAL VENOUS SYSTEM. ...DERIV ARE SECRETED IN URINE & ARE RESPONSIBLE FOR ITS RED COLOR WHEN EXPOSED TO AIR. THEY ALSO APPEAR IN BILE & IN MILK OF LACTATING ANIMALS. URINARY & FECAL EXCRETION OF PHENOTHIAZINE OR ITS DERIV ACCOUNTS FOR 80% OF ORAL DOSE IN SHEEP; FATE OF REMAINING 20% IS UNKNOWN.

URINARY & FECAL EXCRETION OF PHENOTHIAZINE OR ITS DERIV ACCOUNTS FOR 80% OF ORAL DOSE IN SHEEP; FATE OF REMAINING 20% IS UNKNOWN.

ABSORBED BY SKIN.

... Phenothiazine was readily absorbed from the alimentary tract, with the free drug and reddish oxidation products appearing in the urine.

용도 및 제조

Uses · 6건

Used to manufacture veterinary anthelmintics and other pharmaceuticals; [Merck Index, #7252]

MFR OF DYES; PARENT CMPD FOR CHLORPROMAZINE & RELATED ANTIPSYCHOTIC DRUGS; POLYMERIZATION INHIBITOR; ANTIOXIDANT

Used in control of insects that breed in manure

Synthesis of promethazine hydrochloride

Polymerization inhibitor for chloroprene

For more Uses (Complete) data for PHENOTHIAZINE (10 total), please visit the HSDB record page.

U.S. Production2023: 5,500,000 - <7,000,000 lb;2022: 7,000,000 - <8,500,000 lb;2021: 8,500,000 - <10,000,000 lb;2020: 7,000,000 - <8,500,000 lb
Consumer UsesHydraulic fluids;Intermediate;Other;Monomers
Industry UsesIntermediate;Oxidizing agent;Defoamer;Stabilizing agent;Monomers;Processing aids not otherwise specified;Dispersing agent;Other;Binder
Methods of Manufacturing...BY FUSING DIPHENYLAMINE WITH SULFUR; IMPROVED YIELDS WITH IODINE AS CATALYST.
Formulations/Preparations · 2건

DISPERSIBLE POWDERS (36%).

GRADES: TECHNICAL; NF.

응용 분야 · 3건

개요Phenothiazine 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.

용도Phenothiazines 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.

일반 설명Light green to steel-blue powder. Acquires a greenish-brown tint under exposure to sunlight.

공급사50 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
泰安环宇化工有限公司13176825516; 13176825516

추가 설명

정의ChEBI: The 10H-tautomer of phenothiazine.

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