10-[3-(piperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine

• ChemBase ID: 166606
• Molecular Formular: C20H22F3N3S
• Molecular Mass: 393.4689896
• Monoisotopic Mass: 393.14865338
• SMILES: c1ccc2c(c1)N(c1c(S2)ccc(c1)C(F)(F)F)CCCN1CCNCC1
• Canonical SMILES: FC(c1ccc2c(c1)N(CCCN1CCNCC1)c1c(S2)cccc1)(F)F
• InChI: InChI=1S/C20H22F3N3S/c21-20(22,23)15-6-7-19-17(14-15)26(16-4-1-2-5-18(16)27-19)11-3-10-25-12-8-24-9-13-25/h1-2,4-7,14,24H,3,8-13H2
• InChIKey: VYYRFBRPGFAPCM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-[3-(piperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine
• IUPAC Traditional name: 10-[3-(piperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine
• Synonyms: QSS 5; SQ 10018; N-Desmethyl Trifluoperazine Dihydrochloride; Deshydroxyethyl Fluphenazine Dihydrochloride; 10-[3-(1-Piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazine Dihydrochloride; 10-[3-(1-Piperazinyl)propyl]-2-(trifluoromethyl)phenothiazine Dihydrochloride; Demethyltrifluoperazine Dihydrochloride; NSC 644575

Database IDs

• CAS Number: 2804-16-2
• PubChem SID: 162260739
• PubChem CID: 370853

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.0962925
• LogD (pH = 7.4): 2.4280043
• Log P: 4.272876
• Molar Refractivity: 105.6806 cm^3
• Polarizability: 39.5177 Å^3
• Polar Surface Area: 18.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Yellow Solid
• Melting Point: >230°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D295500

A metabolite of the antipsychotic drug Trifluoperazine (TFP). Also a metabolite of Fluphenazine.

REFERENCES

• Mahju, M., et al.: Biochem. Pharmacol., 18, 2701 (1969)
• Breyer, U., et al.: J. Pharm. Sci., 63, 1842 (1969)
• Schmalzing, G., et al.: Drug Metab. Disp., 5, 104 (1969)
• Schmalzing, G., et al.: Xenobiotica, 8, 45 (1969)