1-(4-fluorophenyl)-4-[4-(pyridin-2-yl)piperazin-1-yl]butan-1-one

• ChemBase ID: 122309
• Molecular Formular: C19H22FN3O
• Molecular Mass: 327.3958832
• Monoisotopic Mass: 327.17469056
• SMILES: N1(c2ncccc2)CCN(CC1)CCCC(=O)c1ccc(cc1)F
• Canonical SMILES: Fc1ccc(cc1)C(=O)CCCN1CCN(CC1)c1ccccn1
• InChI: InChI=1S/C19H22FN3O/c20-17-8-6-16(7-9-17)18(24)4-3-11-22-12-14-23(15-13-22)19-5-1-2-10-21-19/h1-2,5-10H,3-4,11-15H2
• InChIKey: XTKDAFGWCDAMPY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-fluorophenyl)-4-[4-(pyridin-2-yl)piperazin-1-yl]butan-1-one
• IUPAC Traditional name: azaperone; 1-(4-fluorophenyl)-4-[4-(pyridin-2-yl)piperazin-1-yl]butan-1-one
• Synonyms: 1-(4-fluorophenyl)-4-(4-(pyridin-2-yl)piperazin-1-yl)butan-1-one; 1-(4-Fluorophenyl)-4-(4-(2-pyridinyl)-1-piperazinyl)-1-butanone; 4′-Fluoro-4-[4-(2-pyridyl)-1-piperazinyl]butyrophenone; Azaperone; 1-(4-Fluorophenyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-1-butanone; 4'-Fluoro-4-[4-(2-pyridyl)-1-piperazinyl]butyrophenone; Fluoperidol; NSC 170976; R-1929; Stresnil; Suicalm; Azaperone; 1-(4-氟苯基)-4-(4-(2-吡啶基)-1-哌嗪基)-1-丁酮; 4′-氟-4-[4-(2-吡啶基)-1-哌嗪基]丁酰苯; 阿扎哌隆

Database IDs

• CAS Number: 1649-18-9
• EC Number: 216-715-8
• MDL Number: MFCD00866692
• PubChem SID: 162216662
• PubChem CID: 15443
• ATC CODE: QN05AD90; QN01AX91
• CHEMBL: 340211
• Chemspider ID: 14695
• KEGG ID: D02620
• Unique Ingredient Identifier: 19BV78AK7W
• Wikipedia Title: Azaperone

CALCULATED PROPERTIES

• Acid pKa: 16.395237
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.3821964
• LogD (pH = 7.4): 3.006676
• Log P: 3.2057927
• Molar Refractivity: 94.2658 cm^3
• Polarizability: 35.395874 Å^3
• Polar Surface Area: 36.44 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 87-89°C; 90-95 °C (194-203°F)

Safety Information

• Storage Condition: Refrigerator
• RTECS: EU4550000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Target: Others
• Admin Routes: intramuscular injection
• Half Life: 4 hours
• Metabolism: hepatic
• Mechanism of Action: 5-HT receptor antagonist; Dopamine antagonist

Product Information

• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Neuroleptic; Psychosedative; Sedative; Vet. tranquilliser
• Empirical Formula (Hill Notation): C19H22FN3O

DETAILS

Sigma Aldrich - 34223

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 34223.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A802200

Sedative; tranquilizer.

REFERENCES

• Heykants, et al.: Arzneim.-Forsch., 21, 982 (1971)
• Stresser, D., et al.: Drug Metab. Dispos., 28, 1440 (1971)
• Egnell, A., et al.: J. Pharmacol. Exp. Ther., 305, 1251 (1971)
• Wester, M., et al.: J. Biol. Chem., 279, 35630 (1971)
• U.S. Pat., 1960, Janssen, 2 958 694; CA, 55, 9439d, (synth)
• Frigerio, A. et al., Org. Mass Spectrom., 1972, 6, 1051, (ms)
• Niemegeers, C.J.E. et al., Arzneim.-Forsch., 1974, 24, 1798, (pharmacol, tox)
• Serrano, L. et al., Res. Vet. Sci., 1976, 20, 316, (pharmacol)
• Koch, M.H.J. et al., Acta Cryst. B, 1977, 33, 1975, (cryst struct)
• Azibi, M. et al., Pharm. Acta Helv., 1981, 56, 190, (polymorphism)
• Van Boven, M. et al., J. Anal. Toxicol., 1992, 16, 33, (metab, chromatogr)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 679
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 9th edn., Van Nostrand Reinhold, 1996, FLU000