1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine dihydrochloride

• ChemBase ID: 105368
• Molecular Formular: C28H34Cl2F2N2O
• Molecular Mass: 523.4851664
• Monoisotopic Mass: 522.20162552
• SMILES: Cl.Cl.Fc1ccc(cc1)C(OCCN1CCN(CCCc2ccccc2)CC1)c1ccc(F)cc1
• Canonical SMILES: Fc1ccc(cc1)C(c1ccc(cc1)F)OCCN1CCN(CC1)CCCc1ccccc1.Cl.Cl
• InChI: InChI=1S/C28H32F2N2O.2ClH/c29-26-12-8-24(9-13-26)28(25-10-14-27(30)15-11-25)33-22-21-32-19-17-31(18-20-32)16-4-7-23-5-2-1-3-6-23;;/h1-3,5-6,8-15,28H,4,7,16-22H2;2*1H
• InChIKey: MIBSKSYCRFWIRU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine dihydrochloride
• IUPAC Traditional name: @vanoxerine dihydrochloride; vanoxerine dihydrochloride
• Synonyms: GBR 12909; 1-(2-bis-Y4-FLUOROPHENYL) METHOXYETHYL)-4-(3-PHENYL-2-PROPYL)PIPERAZINE HYDROCHLORIDE; 1-(2-[bis(4-Fluorophenyl)methoxy]ethyl)-4-(3-phenylpropyl)piperazine dihydrochloride; GBR 12909 dihydrochloride; GBR12909; Vanoxerine (GBR-12909)

Database IDs

• CAS Number: 67469-78-7; 67469-78-7,67469-69-6(freebase),67469-70-9(2Maleicacid)
• MDL Number: MFCD00055193
• PubChem SID: 24277909; 162092808
• PubChem CID: 104920

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.3027139
• LogD (pH = 7.4): 5.039198
• Log P: 6.2421336
• Molar Refractivity: 130.3785 cm^3
• Polarizability: 50.161335 Å^3
• Polar Surface Area: 15.71 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL (Solutions freshly prepared daily)
• Apperance: white solid

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Dopamine Receptor
• Gene Information: human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)

Product Information

• Purity: ≥98% (HPLC); 98%
• Salt Data: HCl

DETAILS

MP Biomedicals - 02159924

Hydrochloride
Purity: 98%
Inhibits the uptake of dopamine.

Sigma Aldrich - D052

Biochem/physiol Actions
Highly selective dopamine reuptake inhibitor with behavioral effects similar to cocaine.

REFERENCES

• Heikkila, R.E., et al., Eur. J. Pharmacol. , 103 : 241 (1984).
• Teicher, M.H., et al., Dev. Brain Res. , 30 : 124 (1986).
• Melia, K.F., et al., J. Pharmacol. Exp. Therap. , 258 : 626 (1991).