StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project：[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HCID 4748Erstellt: 27. Oktober 2026

4-(3-(2-Chlor-10H-phenothiazin-10-yl)propyl)-1-piperazinethanol

Trilafon · Perfenazina · Perphenazin · PZC · F-mon · sch3940 · Decentan · Emesinal

https://huagongshe.com/de/chemical/4748

Molekülstruktur von 4-(3-(2-Chlor-10H-phenothiazin-10-yl)propyl)-1-piperazinethanol

Identifikatoren & physikalische Daten

CAS No.58-39-9
SummenformelC21H26ClN3OS
Durchschnittliche Molmasse404 g/mol
Monoisotopische Masse403,14851113 g/mol
SMILESOCCN1CCN(CCCN2c3ccccc3Sc3ccc(Cl)cc32)CC1
InChIKeyRGCVKNLCSQQDEP-UHFFFAOYSA-N
PubChem CID4748
ChEMBLCHEMBL567
ChEBICHEBI:8028
EC No.200-381-5
DTXSIDDTXSID1023441
Lokaler Name4-(3-(2-Chlor-10H-phenothiazin-10-yl)propyl)-1-piperazinethanol

Chemische & physikalische Eigenschaften

XLogP4,2
Polarare Oberfläche (TPSA)55,3
H-Brücken-Donoren1
H-Brücken-Akzeptoren5
Frei drehbare Bindungen6
Schwere Atome27
Formalladung0
Komplexität463
ArzneimittelDEA NFLIS-Drug Category -> Depressants and TranquilizersPharmaceuticals -> Listed in ZINC15
pHpH = 4.2 - 5.6
LogP (Verteilungskoeffizient)log Kow = 4.203.94.25
GeruchAlmost odorless
GeschmackBitter taste
Color/FormCrystalsWhite to creamy-white powder
LöslichkeitSolubility (mg/mL): ethanol 153acetone 82practically insoluble in sesame oilIn water, 2.83X10-2 g/L (28.3 mg/L) at 24 °C2.37e-02 g/LPractically insoluble in water, freely soluble in methylene chloride, soluble in ethanol (96 per cent). It dissolves in dilute solutions of hydrochloric acid.28.28mg/L(24 ºC)
Human DrugsBreast FeedingLactationMilk, HumanAntipsychotic AgentsPhenothiazinesFDA approved drugs -> Active ingredientPharmaceuticals
Siedepunkt278-281 °C at 1.00E+00 mm HgBP: 214-218 °C at 0.15 mm Hg278-281 at 1 mm Hgbp0.15 214-218°bp1 278-281°
DecompositionWhen heated to decomposition it emits very toxic fumes of /sulfur and nitrogen oxides/ and /hydrogen chloride/.
Schmelzpunkt97 °CCrystals from alcohol, MP: 225-226 °C /Dihydrochloride/95-98C
Physical DescriptionSolid
Dichte1.253
Brechungsindex1.6100 (estimate)
Lagerbedingungen2-8°C
pKa (Säurekonstante)pKa 7.8(H2O,t =24±1) (Uncertain)
AggregatzustandSolid
FarbeWhite
Merck14,7183
StabilitätStable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
Hauptanwendungenclinical testing
InChIInChI=1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2
InChIKeyRGCVKNLCSQQDEP-UHFFFAOYSA-N
SMILESN1(CCO)CCN(CCCN2C3=CC(Cl)=CC=C3SC3=C2C=CC=C3)CC1
CAS Datenbank58-39-9(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-EinstufungDangerH302 (96.3%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P320, P321, P330, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 54 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Weitere SicherheitsinformationenIMAP assessments - 1-Piperazineethanol, 4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-: Environment tier I assessment
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including perfenazine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Hazard Classes and CategoriesAcute Tox. 4 (96.3%)
Skin, Eye, and Respiratory IrritationsMay cause irritation /to the eyes, skin, and mucous membranes/. Avoid inhalation. Remove to fresh air. Avoid contact. Flush /eyes/ with copious quantities of tepid water. Avoid /skin/ contact. Flush with copious quantities of soap and water.
Hazardous Reactivities and IncompatibilitiesPerphenazine should not be mixed with tea as precipatation of insoluble tannates may occur.
BrandbekämpfungsverfahrenWater spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials.As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
LagerbedingungenStore in tight, light-resistant container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.Commercially available preparations of perphenazine should be stored in tight, light-resistant containers. Perphenazine tablets and oral concentrate solution should be stored at 2-25 and 2-30 °C, respectively

Anwendungen & Verwendung

Verwenden

D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro. Antipsychotic.

freezing of the oral concentrate solution should be avoided.
ReinigungsverfahrenWear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.
EntsorgungsverfahrenSRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
Preventive MeasuresSRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.This material is assumed to be combustible. As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.Use safety glasses or goggles and protect exposed skin.
Personal Protective Equipment (PPE)Engineering controls such as exhaust ventilation are recommended.Use a NIOSH approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.
TreatmentTreatment is symptomatic and supportive. Induction of emesis is not recommended because of the possibility of a seizure, CNS depression, or dystonic reaction of the head or neck and subsequent aspiration. Gastric lavage (after intubation, if the patient is unconscious) and administration of activated charcoal together with a laxative should be considered. There is no specific antidote. Standard measures (oxygen, intravenous fluids, corticosteroids) should be used to manage circulatory shock or metabolic acidosis. An open airway and adequate fluid intake should be maintained. Body temperature should be regulated. Hypothermia is expected, but severe hyperthermia may occur and must be treated vigorously. An electrocardiogram should be taken and close monitoring of cardiac function instituted if there is any sign of abnormality. Close monitoring of cardiac function is advisable for not less than five days. Vasopressors such as norepinephrine may be used to treat hypotension, but epinephrine should NOT be used. (L1712)
WechselwirkungenSince phenothiazines and central nervous system depressants (opiates, analgesics, antihistamines, barbiturates) can potentiate each other, less than the usual dosage of the added drug is recommended and caution is advised when they are administered concomitantly.Perphenazine ... increased t1/2 of amphetamine in brain. However, despite elevated amphetamine levels, amphetamine-induced pharmacological effects were inhibited.It appears that whether given im or orally, antiparkinsonism drugs biperidine & orphenadine have no significant effect on previously attained levels of perphenazine and its metabolites in psychotic pt.QT interval-prolonging medications, including cisapride, erythromycin, and quinidine /may produce/ additive QT interval prolongation increasing the risk of developing cardiac arrhythmias when /concurrently administered with phenothiazines/. /Phenothiazines/For more Interactions (Complete) data for Perphenazine (31 total), please visit the HSDB record page.
HepatotoxicityTransient liver test abnormalities occur in a proportion of patients on long term therapy with perphenazine and other phenothiazines, but the elevations are usually mild, asymptomatic and reverse even with continuation of medication. Chlorpromazine, the prototype phenothiazine, is a well known cause clinically apparent acute liver injury which occurs in approximately 1% of treated patients. It is unclear whether perphenazine causes a similar syndrome, but if so, it is rare and far less common than with chlorpromazine. Case series of drug induced liver injury have occasionally listed perphenazine as a cause, but the clinical characteristics of the injury have not been described. Typical phenothiazine induced liver injury usually presents within 1 to 4 weeks of starting therapy, with a cholestatic or mixed pattern of serum enzyme elevations. Immunoallergic manifestations (fever and eosinophilia) are common but usually not prominent, and autoantibodies are rare. Phenothiazine induced jaundice can be severe and prolonged and result in vanishing bile duct syndrome, but is rarely fatal.
ExpositionspfadeAbsolute bioavailability is 40% following oral administration.
Milk ConcentrationsPhenothiazines are distributed into milk. The manufacturers warn that nursing should not be undertaken by women receiving phenothiazines. /Phenothiazine General Statement/
ToxizitätsübersichtBinds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. The mechanism of the anti-emetic effect is due predominantly to blockage of the dopamine D2 neurotransmitter receptors in the chemoreceptor trigger zone and vomiting centre. Perphenazine also binds the alpha andrenergic receptor. This receptor's action is mediated by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.
Signs and SymptomsSymptoms of overdose include stupor or coma, and children may have convulsive seizures. Signs of arousal may not occur for 48 hours.
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ The toxic effects of perphenazine are typically mild to moderate with death occurring in cases involving a large overdose. Overdosage of perphenazine primarily involves the extrapyramidal mechanism and produces the same adverse reactions /of phenothiazines/, but to a more marked degree. It is usually evidenced by stupor or comachildren may have convulsive seizures. Signs of arousal may not occur for 48 hours. The primary effects of medical concern are cardiac in origin including tachycardia, prolongation of the QRS or QTc intervals, atrioventricular block, torsade de pointes, ventricular dysrhythmia, hypotension or cardiac arrest, which indicate serious poisoning. Deaths by deliberate or accidental overdosage have occurred with this class of drugs./SIGNS AND SYMPTOMS/ In general, overdosage of phenothiazines may be expected to produce effects that are extensions of common adverse reactionssevere extrapyramidal reactions, hypotension, and sedation have been the principal effects reported. CNS depression progressing to coma with areflexia or CNS stimulation with convulsions followed by respiratory depression may occurpatients with early or mild intoxication may experience drowsiness, restlessness, disorientation, confusion, and excitement. Other reported effects associated with acute phenothiazine overdosage have included shock (eg, ECG changes and cardiac arrhythmias), increased QT and PR intervals, non-specific ST and T wave changes, bradycardia, sinus tachycardia, bilateral bundle branch block, atrioventricular block, ventricular tachycardia, ventricular fibrillation, torsades de pointes, myocardial depression, agitation, dry skin, nasal congestion, urinary retention, oliguria, uremia, blurred vision, hypothermia, hyperthermia, mydriasis, miosis, tremor, muscle twitching, spasm or rigidity, seizures, muscular hypotonia, constipation, ileus, dry mouth, vomiting, difficulty in swallowing or breathing, cyanosis, and respiratory and/or vasomotor collapse, and pulmonary edema, possibly with sudden apnea. /Phenothiazine general Statement//SIGNS AND SYMPTOMS/ Sudden and unexpected deaths have occurred in patients receiving phenothiazines, especially during long-term administration of the drugs. In some patients, sudden death appeared to result from asphyxia (secondary to failure of the cough reflex) or cardiac arrest. /Phenothiazine General Statement//CASE REPORTS/ A small number of cases have been presented in the world literature in which treatment with phenothiazines resulted in clinical and laboratory manifestations of systemic lupus erythematosus (SLE). The clinical picture of such patients tends to be "symptom poor". A 26-year-old patient is presented who had a 7-year history of treatment for a schizophrenic illness and developed clinical as well as laboratory evidence for SLE. The differential diagnosis included: a) phenothiazine-induced SLEb) SLE presenting with psychosis as a symptomand c) SLE and sychosis occurring independently. The patient had a complete medical and neuropsychiatric work-up and was followed for 12 months. This challenging diagnostic problem is discussed. Phenothiazine-induced SLE was the most likely diagnosis. Although the possibility of two diseases occurring independently in the same person did not explain the clinical and laboratory data, it is difficult to rule out this possibility completely. SLE presenting with psychosis as a symptom could be ruled out by the work-up and history.For more Human Toxicity Excerpts (Complete) data for Perphenazine (13 total), please visit the HSDB record page.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)PerphenazinevLess-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Perphenazine (PER), a potent phenothiazine, was administered to rats in a dose of 5 mg/kg, IP, daily for 19 days (experiment I) and 26 days (experiment II). In the first experiment, weights 3 days after treatment ended were PER 308 +/- 16 gm and saline controls 329 +/- 25 gm (P less than 0.01). Lengths were also smaller (221 +/- 2.2 mm vs 230 +/- 1.0 mm, P less than 0.05), and the slope of the growth curves for weight and length differed significantly as well. In a second experiment, the liquid diet pair-feeding technique was employed and demonstrated that the growth retardation due to PER could not be accounted for by a decrease in food intake. Pair-fed saline-treated rats who ate 2% less than PER-treated rats had a weight of 264 +/- 6 gm at the end of treatment compared to 236 +/- 9 gm for PER treated (P less than 0.01). It is concluded that PER treatment produces growth retardation and that this is not due simply to decreased food intake. The inhibition of growth hormone secretion produced by PER may be the mechanism of its growth-retarding effect./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Perphenazine in doses of 10--50 mg kg-1 day-1 given at the early stages of pregnancy delayed nidation up to day 8 of pregnancy. Once nidation had occurred the length of the rest of the gestation period was normal. Doses of up to 20 mg perphenazine kg-1 day-1, injected on days 1--7, prolonged gestation but the mothers and young were apparently normallower doses were effective only when treatment commenced soon after copulation. The delay in implantation of the ovum caused by perphenazine was corrected and and implantation was brought about immediately, by injection of 0.1 microgram oestradiol together with perphenazine. It is suggested that perphenazine delays and prevents implantation in rats by counteracting oestrogen release from the ovaries./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ The teratogenic effect of perphenazine was studied in closed-bred Wistar rats. Rats were given the substance orally continuously on days 7 to 14 of pregnancy, or as a single dose on one of days 9-15. The doses were considerably higher than the specific neuroleptic doses of perphenazine (20-150 mg/kg). The fetal mortality and malformation rates were significantly higher in the perphenazine-treated groups than in the controls. The results were compared with the earlier results of methophenazine treatment. Perphenazine was found to be more toxic for rat embryos than methophenazine./OTHER TOXICITY INFORMATION/ In rats with mammary tumors sc administration of 5 mg/kg of perphenazine daily for 14 days after ovariectomy, produced increases in prolactin concentrations and either regression or growth of certain tumors.
Populations at Special RiskThe pharmacokinetics of perphenazine covary with the hydroxylation of debrisoquine which is mediated by cytochrome P450 2D6 (CYP 2D6) and thus is subject to genetic polymorphism - ie, 7% to 10% of Caucasians and a low percentage of Asians have little or no activity and are called "poor metabolizers." Poor metabolizers of CYP 2D6 will metabolize perphenazine more slowly and will experience higher concentrations compared with normal or "extensive" metabolizers.Geriatric patients appear to be particularly sensitive to adverse nervous system (eg, tardive dyskinesia, parkinsonian signs and symptoms, akathisia, sedation), anticholinergic, and cardiovascular (eg, orthostatic hypotension) effects of antipsychotic agents. Because the risk of falling and associated hip fracture in geriatric patients may be increased with use of antipsychotic agents, phenothiazine therapy should be initiated at reduced dosages and such patients observed closely. /Phenothiazine General Statement/
Wassergefährdungsklasse (WGK)3
UN-TransportnummerUN 2811 6.1 / PGII
Zollcode29349990
RTECS-Nr.TL7175000
R-Sätze (R)22-43
ToxizitätLD50 oral in rat: 318mg/kg
GefahrensymboleXn
Sicherheitshinweise (S)28-36/37/39-45
Lagerklasse3 - Flammable liquids
Gefahrstoffdaten58-39-9(Hazardous Substances Data)
GefahrenklasseAcute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1