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Name |
Perphenazine |
EINECS | 200-381-5 |
CAS No. | 58-39-9 | Density | 1.253 g/cm3 |
PSA | 55.25000 | LogP | 3.88350 |
Solubility | 28.28mg/L(24 oC) | Melting Point |
35339ºC |
Formula | C21H26ClN3OS | Boiling Point | 580.4 °C at 760 mmHg |
Molecular Weight | 403.976 | Flash Point | 304.8 °C |
Transport Information | N/A | Appearance | Off-white to pale yellow solid |
Safety | 28-36/37/39-45 | Risk Codes | 22-43 |
Molecular Structure | Hazard Symbols | Xn | |
Synonyms |
1-Piperazineethanol,4-[3-(2-chlorophenothiazin-10-yl)propyl]- (8CI);1-(2-Hydroxyethyl)-4-[3-(2-chloro-10-phenothiazinyl)propyl]piperazine;2-Chloro-10-3-[1-(2-hydroxyethyl)-4-piperazinyl] propyl phenothiazine;2-Chloro-10-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]phenothiazine;Chloriprozine;Chlorperphenazine;Decentan;Emesinal;Etaperazin;Etaperazine;Ethaperazine;Fentazin;Fentazin syrup;Fentazine duolets;Mutabom;NSC 150866;PZC;Perfenazine;Perfenil;Perphenan;Perphenazin;Sch 3940;Thilatazin;Tranquisan;Trifaron;Trilafon;Trilifan;Triphenot;g-[4-(b-Hydroxyethyl)piperazin-1-yl]propyl-2-chlorophenothiazine;4-(3-(2-Chlorophenothiazin-10-yl)propyl)-1-piperazineethanol; |
Article Data | 11 |
Conditions | Yield |
---|---|
With potassium carbonate; toluene |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaNH2; liquid NH3 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaI; butanone 2: K2CO3; toluene View Scheme |
Conditions | Yield |
---|---|
In acetonitrile at 0 - 40℃; for 6h; Product distribution / selectivity; |
N-(tert-butoxycarbonyl)-4-aminobutanoic acid
perphenazine
A
5,6-dhydrouracil
B
perphenazine N-Boc-4-aminobutyrate
Conditions | Yield |
---|---|
Stage #1: N-(tert-butoxycarbonyl)-4-aminobutanoic acid; perphenazine With dmap In dichloromethane at 0 - 5℃; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Product distribution / selectivity; | A n/a B 98% |
N-(tert-butoxycarbonyl)-4-aminobutanoic acid
perphenazine
perphenazine N-Boc-4-aminobutyrate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; | 98% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; Product distribution / selectivity; Industry scale; Inert atmosphere; | 98% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 4h; Product distribution / selectivity; | 97% |
perphenazine
perphenazine sulfoxide
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water for 2h; | 95% |
perphenazine
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With C47H70BrO4PPdSi; sodium t-butanolate In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Inert atmosphere; Sealed tube; | 92% |
N-(tert-butoxycarbonyl)-4-aminobutanoic acid
perphenazine
B
perphenazine N-Boc-4-aminobutyrate
Conditions | Yield |
---|---|
Stage #1: N-(tert-butoxycarbonyl)-4-aminobutanoic acid; pivaloyl chloride With triethylamine In tetrahydrofuran Stage #2: perphenazine In tetrahydrofuran at 50℃; for 16h; Product distribution / selectivity; | A n/a B 90% |
The IUPAC name of Perphenazine is 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethanol. With the CAS registry number 58-39-9, it is also named as 1-Piperazineethanol, 4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)-. The product's categories are Organics; Antagonists Forensic and Veterinary Standards; Chemical Structure; Dopaminergics; Drugs & Metabolites; Neat Compounds Drugs of Abuse; Neurotransmitters; Others. Besides, it is white crystalline powder, which should be stored at 2-8 °C. In addition, its molecular formula is C21H26ClN3OS and molecular weight is 403.97.
The other characteristics of this product can be summarized as: (1)EINECS: 200-381-5; (2)ACD/LogP: 4.34; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.88; (5)ACD/LogD (pH 7.4): 4.21; (6)ACD/BCF (pH 5.5): 40.74; (7)ACD/BCF (pH 7.4): 863.6; (8)ACD/KOC (pH 5.5): 190.38; (9)ACD/KOC (pH 7.4): 4036; (10)#H bond acceptors: 4; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 7; (13)Index of Refraction: 1.626; (14)Molar Refractivity: 114.22 cm3; (15)Molar Volume: 322.3 cm3; (16)Surface Tension: 50.9 dyne/cm; (17)Density: 1.253 g/cm3; (18)Flash Point: 304.8 °C; (19)Melting Point: 97 °C; (20)Water Solubility: 28.3 mg/L at 24 °C; (21)Enthalpy of Vaporization: 91.32 kJ/mol; (22)Boiling Point: 580.4 °C at 760 mmHg; (23)Vapour Pressure: 2.6E-14 mmHg at 25 °C.
Production of Perphenazine: frist, you can use N-(2-Hydroxyethyl) piperazine to produce 1-(3-Chloropropyl)-4-(2-hydroxyethyl) piperazine by condensation with Trimethylene bromochloride. And then please use it to produce crude product by condensation with 2-Chlorophenothiazine. Afterwards, you will obtain this chemical after recrystallize it by the use of Ethyl acetate.
Uses of Perphenazine: this chemical is a typical antipsychotic drug to treat psychosis (e.g. in schizophrenics) and the manic phases of bipolar disorder. It also can be used to treat agitated depression (together with an antidepressant) in low doses. Furthermore, it can be used to produce 2-{4-[3-(2-Chloro-5-oxo-5H-5l4-phenothiazin-10-yl)-propyl]-πperazin-1-yl}-ethanol.
This reaction needs NaNO2, HCl and H2O for 2 hours. The yield is 95 %.
When you are using this chemical, please be cautious about it as the following: it is harmful if swallowed. And it also may cause sensitization by skin contact. You should wear suitable protective clothing, gloves and eye/face protection. After contact with skin, please wash immediately with plenty of soap-suds. Moreover, in case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
People can use the following data to convert to the molecule structure.
(1)SMILES: Clc2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCN(CCO)CC4
(2)InChI: InChI=1/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
(3)InChIKey: RGCVKNLCSQQDEP-UHFFFAOYAP
(4)Std. InChI: InChI=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
(5)Std. InChIKey: RGCVKNLCSQQDEP-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 32mg/kg (32mg/kg) | Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972. | |
cat | LD50 | intravenous | 35mg/kg (35mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960. |
cat | LD50 | subcutaneous | > 2500ug/kg (2.5mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961. | |
cat | LDLo | oral | 1gm/kg (1000mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960. |
dog | LD50 | intravenous | 51mg/kg (51mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: REGIDITY GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960. |
dog | LD50 | subcutaneous | > 20mg/kg (20mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961. | |
human | TDLo | intramuscular | 71428ng/kg (0.071428mg/kg) | BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | British Medical Journal. Vol. 3, Pg. 867, 1967. |
monkey | LD50 | subcutaneous | > 510ug/kg (0.51mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961. | |
mouse | LD50 | intraperitoneal | 64mg/kg (64mg/kg) | Journal of Pharmaceutical Sciences. Vol. 59, Pg. 976, 1970. | |
mouse | LD50 | intravenous | 19mg/kg (19mg/kg) | BEHAVIORAL: ATAXIA BEHAVIORAL: REGIDITY | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961. |
mouse | LD50 | oral | 120mg/kg (120mg/kg) | "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 185, 1973. | |
mouse | LD50 | subcutaneous | > 80mg/kg (80mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961. |
pigeon | LD50 | intramuscular | 250mg/kg (250mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960. |
pigeon | LD50 | intravenous | 32mg/kg (32mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 638, 1960. |
rat | LD50 | intraperitoneal | 146mg/kg (146mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 917, 1974. | |
rat | LD50 | intravenous | 34mg/kg (34mg/kg) | Farmaco, Edizione Pratica. Vol. 26, Pg. 585, 1971. | |
rat | LD50 | oral | 318mg/kg (318mg/kg) | Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972. | |
rat | LD50 | subcutaneous | > 80mg/kg (80mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 932, 1961. |