ChemicalBook > CAS DataBase List > FLUPHENAZINE

FLUPHENAZINE

Product Name
FLUPHENAZINE
CAS No.
69-23-8
Chemical Name
FLUPHENAZINE
Synonyms
Permitil;Fluphenazine Decanoate EP Impurity B;s94;S 94;Elinol;sq4918;Pacinol;Sevinol;SQ 4918;dapotum
CBNumber
CB7107784
Molecular Formula
C22H26F3N3OS
Formula Weight
437.52
MOL File
69-23-8.mol
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FLUPHENAZINE Property

Melting point:
268-274℃
Boiling point:
bp0.5 268-274°; bp0.3 250-252°
Density 
1.2156 (estimate)
RTECS 
TL9730000
Flash point:
9℃
storage temp. 
-20°C
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Sticky Solid
pka
pKa 7.98±0.03(H2O t=20±0.5) (Uncertain)
color 
Dark-brown viscous oil
Water Solubility 
31.06mg/L(37 ºC)
Stability:
Hygroscopic
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Safety

Hazard Codes 
F,T
Risk Statements 
11-23/24/25-39/23/24/25
Safety Statements 
16-36/37-45
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
1
HazardClass 
6.1
Hazardous Substances Data
69-23-8(Hazardous Substances Data)
Toxicity
LD50 oral in mouse: 220mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H301Toxic if swalloed

H370Causes damage to organs

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P311Call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P405Store locked up.

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N-Bromosuccinimide Price

Alfa Aesar
Product number
J61179
Product name
Fluphenazine, 98+%
Packaging
1g
Price
$124
Updated
2021/12/16
Alfa Aesar
Product number
J61179
Product name
Fluphenazine, 98+%
Packaging
5g
Price
$251
Updated
2021/12/16
Cayman Chemical
Product number
23555
Product name
Fluphenazine
Purity
≥95%
Packaging
1g
Price
$105
Updated
2021/12/16
Cayman Chemical
Product number
23555
Product name
Fluphenazine
Purity
≥95%
Packaging
500mg
Price
$55
Updated
2021/12/16
TRC
Product number
F598418
Product name
Fluphenazine
Packaging
10mg
Price
$85
Updated
2021/12/16
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FLUPHENAZINE Chemical Properties,Usage,Production

Originator

Prolixin, Squibb ,US ,1959

Uses

Antipsychotic.

Uses

Fluphenazine is an extremely strong antipsychotic drug. A stimulatory effect accompanies the neuroleptic effect. It is used in psychiatry for treating various forms of schizophrenia and other mental illnesses.

Definition

ChEBI: A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl group at the N-10 position.

Manufacturing Process

A suspension of 69.0 grams of 2-trifluoromethylphenothiazine in 1 liter of toluene with 10.9 grams of sodium amide is heated at reflux with high speed stirring for 15 minutes. A solution of 54.1 grams of 1-formyl-4-(3'chloropropyl)-piperazine, [prepared by formylating 1-(3'-hydroxypropyl)piperazine by refluxing in an excess of methyl formate, purifying the 1-formyl4-(3'-hydroxypropyl)-piperazine by vacuum distillation, reacting this compound with an excess of thionyl chloride at reflux and isolating the desired 1-formyl-4(3'-chloropropyl)-piperazine by neutralization with sodium carbonate solution followed by distillation] in 200 ml of toluene is added. The reflux period is continued for 4 hours. The cooled reaction mixture is treated with 200 ml of water. The organic layer is extracted twice with dilute hydrochloric acid. The acid extracts are made basic with ammonia and extracted with benzene. The volatiles are taken off in vacuo at the steam bath to leave a dark brown oil which is 10-[3'-(N-formylpiperazinyl)-propyl]-2trifluoromethylphenothiazine. It can be distilled at 260°C at 10 microns, or used directly without distillation if desired.
A solution of 103.5 grams of 10-[3'-(N-formylpiperazinyl)-propyl]-2trifluoromethylphenothiazine in 400 ml of ethanol and 218 ml of water containing 26 ml of 40% sodium hydroxide solution is heated at reflux for 2 hours. The alcohol is taken off in vacuo on the steam bath. The residue is swirled with benzene and water. The dried benzene layer is evaporated in vacuo. The residue is vacuum distilled to give a viscous, yellow oil, 10(3'piperazinylpropyl)-2-trifluoromethylphenothiazine, distilling at 210° to235°C at 0.5 to 0.6 mm.
A suspension of 14.0 grams of 10-(3'-piperazinylpropyl)-2trifluoromethylphenothiazine, 6.4 grams of β-bromoethyl acetate and 2.6 grams of potassium carbonate in 100 ml of toluene is stirred at reflux for 16 hours. Water (50 ml) is added to the cooled mixture. The organic layer is extracted into dilute hydrochloric acid. After neutralizing the extracts and taking the separated base up in benzene, a viscous, yellow residue is obtained by evaporating the organic solvent in vacuo. This oil is chromatographed on alumina. The purified fraction of 7.7 grams of 10-[3'-(Nacetoxyethylpiperazinyl)-propyl] -2-trifluoromethylphenothiazine is taken up in ethyl acetate and mixed with 25 ml of alcoholic hydrogen chloride. Concentration in vacuo separates white crystals of the dihydrochloride salt, MP 225° to 227°C.
A solution of 1.0 gram of 10-[3'-(N-acetoxyethylpiperazinyl)-propyl]-2trifluoromethylphenothiazine in 25 ml of 1 N hydrochloric acid is heated at reflux briefly. Neutralization with dilute sodium carbonate solution and extraction with benzene gives the oily base, 10-[3'-(N-βhydroxyethylpiperazinyl)-propyl]-2-trifluoromethylphenothiazine. The base is reacted with an excess of an alcoholic hydrogen chloride solution. Trituration with ether separates crystals of the dihydrochloride salt, MP 224° to 226°C, (from US Patent 3,058,979).

Therapeutic Function

Tranquilizer

Safety Profile

Poison by ingestion,intraperitoneal, and intravenous routes. Moderately toxicby subcutaneous route. Experimental reproductive effects.When heated to decomposition it emits very toxic fumesof Fí, NOx, and SOx.

Synthesis

Fluphenazine, 4-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]-1- piperazineethanol (6.1.8), is synthesized by any of the methods described above [21¨C27]. Alkylation of 2-trifluoromethylphenothiazine using 4-formyl-1-piperazineylpropylchloride in the presence of sodium amide synthesizes 2-trifluoromethyl-10-[3-(4-formyl- 1-piperazinyl)propyl]phenothizine (6.1.6). Further alkaline hydrolysis removes the N-formyl group, giving 2-trifluoromethyl-10-[3-(1-piperazinyl)propyl]phenothiazine (6.1.7). This is alkylated by 2-bromethanol-1 acetate, which upon further acidic hydrolysis removes the protecting acetyl group, yielding fluphenazine (6.1.8) [27,28].

FLUPHENAZINE Preparation Products And Raw materials

Raw materials

Preparation Products

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FLUPHENAZINE Suppliers

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View Lastest Price from FLUPHENAZINE manufacturers

Dideu Industries Group Limited
Product
FLUPHENAZINE 69-23-8
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-07-23

69-23-8, FLUPHENAZINERelated Search:


  • 1-(2-hydroxyethyl)-4-(3-(trifluoromethyl-10-phenothiazinyl)propyl)-piperazine
  • 10-(3-(2-Hydroxyethyl)piperazinopropyl)-2-(trifluoromethyl)phenothiazine
  • 10-(3’-(4"-(beta-hydroxyethyl)-1"-piperazinyl)-propyl)-3-trifluoromethylphenot
  • 1-Piperazineethanol, 4-[3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-
  • 1-Piperazineethanol, 4-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]-
  • 1-piperazineethanol,4-(3-(2-(trifluoromethyl)-10h-phenothiazin-10-yl)propyl)
  • 2-(4-(3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl)-1-piperazinyl)ethanol
  • moditen(tablorelixir)
  • Pacinol
  • Permitil
  • Phenothiazine, 10-(3-(4-(2-hydroxyethyl)-1-piperazinyl)propyl)-2-(trifluoromethyl)-
  • phenothiazine,10-(3-(4-(2-hydroxyethyl)-1-piperazinyl)propyl)-2-(trifluorome
  • phenothiazine,10-(3-(4-(2-hydroxyethyl)-1-piperazinyl)propyl-2-(trifluoromethy
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  • 4-(3-(2-(trifluoromethyl)-10h-phenothiazin-10-yl)propyl)-1-piperazineethanol
  • 4-(3-(2-(trifluoromethyl)phenothiazin-10-yl)propyl)-1-piperazineethano
  • 4-(3-(2-Trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanol
  • 4-(3-(-trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanol
  • 4-[3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-1-piperazineethanol
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  • kitasamycin,leucomycin
  • 2-(4-{3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethanol
  • Fluphenazine dihydrochloride solution
  • FLUPHENAZINE USP/EP/BP
  • Fluphenazine HydrochlorideQ: What is Fluphenazine Hydrochloride Q: What is the CAS Number of Fluphenazine Hydrochloride Q: What is the storage condition of Fluphenazine Hydrochloride
  • Fluphenazine free base
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  • Fluphenazine-D6 hydrochloride
  • 69-23-8
  • C22H26F3N3OS
  • Dopamine receptor