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58-39-9

Basic Information
CAS No.: 58-39-9
Name: 1-Piperazineethanol,4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-
Molecular Structure:
Molecular Structure of 58-39-9 (1-Piperazineethanol,4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-)
Formula: C21H26ClN3OS
Molecular Weight: 403.97
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;
EINECS: 200-381-5
Density: 1.253 g/cm3
Melting Point: 35339ºC
Boiling Point: 580.4 °C at 760 mmHg
Flash Point: 304.8 °C
Solubility: 28.28mg/L(24 oC)
Appearance: Off-white to pale yellow solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-43
Safety: 28-36/37/39-45
Transport Information:
PSA: 55.25000
LogP: 3.88350
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Specification

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.