Trifluoperazine dihydrochloride Chemical Properties

Melting point:

243 °C (dec.)(lit.)

Flash point:

9℃

storage temp. 

-20°C

solubility 

ethanol: soluble5mg/mL

pka

pK1 3.9, pK2 8.1(at 25℃)

form 

powder

color 

white to off-white

λmax

312nm(MeOH)(lit.)

Merck 

14,9680

BRN 

3820024

Stability:

Hygroscopic

CAS DataBase Reference

440-17-5(CAS DataBase Reference)

EPA Substance Registry System

10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride (440-17-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

3

RTECS 

SP1750000

F 

3-10

HS Code 

29343000

MSDS

• Language:English Provider:SigmaAldrich

Trifluoperazine dihydrochloride Usage And Synthesis

Description

Trifluoperazine (TFP) is a phenothiazine compound with anti-adrenergic and anti-dopaminergic actions typical of antipsychotic agents. It antagonizes adrenergic receptors, with selectivity for α₁ over the α₂ subtypes (K_is = 24, 653, 163, and 391 nM for α_1A, α_2A, α_2B, and α_2C, respectively). TFP binds with much higher affinity to the dopamine D₂-like receptor (K_d = 0.96 nM) compared to the dopamine D₄-like and the serotonin 5-HT_2A receptors (K_ds = 44 and 135 nM, respectively). Furthermore, TFP antagonizes calmodulin (CaM) and alters the calcium-binding properties of calsequestrin (CSQ). TFP has been shown to activate type-2 ryanodine receptors independently of its CaM and CSQ activity.

Chemical Properties

Cream Fine Powder

Originator

Stelazine,SKF,US,1958

Uses

Trifluoperazine dihydrochloride has been used as a calmodulin kinase antagonist in cultured Aplysia californica neurons. Trifluoperazine dihydrochloride has also been used as a PMCA inhibitor in mouse duodenal tissues to block the transcellular active calcium flux.

Uses

Antipsychotic

Manufacturing Process

A mixture of 17.2 grams of 2-trifluoromethylphenothiazine, 3.1 grams of sodamide and 14 grams of 1-(3'-chloropropyl)-4-methylpiperazine in 200 ml of xylene is heated at reflux for 2 hours. The salts are extracted into 150 ml of water. The xylene layer is then extracted with several portions of dilute hydrochloric acid. The acid extracts are combined and neutralized with ammonium hydroxide solution. The product, 10-[3'-(4''-methyl-1''- piperazinyl)-propyl]-2-trifluoromethylphenothiazine, is taken into benzene and purified by vacuum distillation, BP 202° to 210°C at 0.6 mm.

Therapeutic Function

Tranquilizer

General Description

Trifluoperazinehydrochloride, 10-[3-(4-Methyl-1-piperazinyl)propyl-[2-(trifluoromethyl)phenothiazine dihydrochloride (Stelazine).The absorption of trifluoperazine is erratic and variable andit is widely distributed into tissues. The excretion of trifluoperazineoccurs 50% via kidneys and the other 50% isthrough enterohepatic circulation. The metabolism and druginteractions of trifluoperazine are the same as with the otherphenothiazines. Trifluoperazine does not show any specificdrug interactions. Trifluoperazine is indicated for the managementof schizophrenia and short-term treatment ofnonpsychotic anxiety.

Biochem/physiol Actions

Trifluoperazine dihydrochloride is useful in treating schizophrenia, disturbed behavior, severe anxiety, nausea and vomiting.

Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of F-, NOx, SOx, and HCl. See also FLUORIDES.

Purification Methods

Recrystallise the salt from absolute EtOH, filter the crystals, dry them in vacuo and store them in tightly stoppered bottles because it is hygroscopic. It is soluble in H2O but insoluble in *C6H6, Et2O and alkaline aqueous solution. It has UV at 258 and 307.5nm (log 4.50 and 3.50) in EtOH (neutral species). [Craig max et al. J Org Chem 22 709 1957.] It is a calmodulin inhibitor [Levene & Weiss J Parmacol Exptl Ther 208 454 1978] and is a psychotropic agent [Fowler Arzneim.-Forsch 27 866 1977]. [Beilstein 27 III/IV 1353.]

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