| Identification | More | [Name]
Trifluoperazine dihydrochloride | [CAS]
440-17-5 | [Synonyms]
10-[3-(4-METHYL-1-PIPERAZINYL)PROPYL]-2-TRIFLUOROMETHYL-PHENOTHIAZINE DIHYDROCHLORIDE
10-[3-(4-METHYLPIPERAZIN-1-YL)PROPYL]-2-(TRIFLUOROMETHYL)-10H-PHENOTHIAZINE DIHYDROCHLORIDE
LABOTEST-BB LT00452002
STELAZINE
STELAZINE DIHYDROCHLORIDE
TRIFLUOPERAZINE 2HCL
TRIFLUOPERAZINE DIHYDROCHLORIDE
TRIFLUOPERAZINE HCL
TRIFLUOPERAZINE HYDROCHLORIDE
10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-phenothiazindihy
10-(3-(4-methyl-1-piperazinyl)propyl)-2-trifluoromethylphenothiazinedihydroc
10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10h-phenothiazin
eskazine
skf5019
trifluoroperazinedihydrochloride
trifluoroperazinehydrochloride
trifluoropyrazindihydrochloride
trifluperazinedihydrochloride
triphthazinedihydrochloride
tryptazine | [EINECS(EC#)]
207-123-0 | [Molecular Formula]
C21H26Cl2F3N3S | [MDL Number]
MFCD00012656 | [Molecular Weight]
480.42 | [MOL File]
440-17-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Cream Fine Powder | [Melting point ]
243 °C (dec.)(lit.) | [Fp ]
9℃ | [storage temp. ]
2-8°C
| [solubility ]
ethanol: soluble5mg/mL | [form ]
powder | [pka]
pK1 3.9, pK2 8.1(at 25℃) | [color ]
white to off-white | [Water Solubility ]
water: 50g/L, clear | [Usage]
Antipsychotic | [λmax]
312nm(MeOH)(lit.) | [Merck ]
13,9753 | [BRN ]
3820024 | [Stability:]
Hygroscopic | [CAS DataBase Reference]
440-17-5(CAS DataBase Reference) | [EPA Substance Registry System]
440-17-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [RIDADR ]
UN1230 - class 3 - PG 2 - Methanol, solution | [WGK Germany ]
3
| [RTECS ]
SP1750000
| [F ]
3-10 | [TSCA ]
TSCA listed | [HazardClass ]
9 | [HS Code ]
29343000 | [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. |
| Hazard Information | Back Directory | [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 (Kis = 24, 653, 163, and 391 nM for α1A, α2A, α2B, and α2C, respectively).1 TFP binds with much higher affinity to the dopamine D2-like receptor (Kd = 0.96 nM) compared to the dopamine D4-like and the serotonin 5-HT2A receptors (Kds = 44 and 135 nM, respectively).2 Furthermore, TFP antagonizes calmodulin (CaM) and alters the calcium-binding properties of calsequestrin (CSQ).3,4 TFP has been shown to activate type-2 ryanodine receptors independently of its CaM and CSQ activity.4 | [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. | [storage]
Store at -20°C | [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.] | [References]
[1] M ZIMMER F H. Calmodulin antagonists inhibit activity of myosin light-chain kinase independent of calmodulin.[J]. European journal of biochemistry, 1984, 142 2: 393-397. DOI: 10.1111/j.1432-1033.1984.tb08300.x
[2] JIA QIN. Trifluoperazine: a rynodine receptor agonist.[J]. Pflugers Archiv?: European journal of physiology, 2009, 458 4: 643-651. DOI: 10.1007/s00424-009-0658-y |
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