1-[bis(4-fluorophenyl)methyl]-4-[(2,3,4-trimethoxyphenyl)methyl]piperazine dihydrochloride

• ChemBase ID: 154901
• Molecular Formular: C27H32Cl2F2N2O3
• Molecular Mass: 541.4573864
• Monoisotopic Mass: 540.17580469
• SMILES: COc1ccc(c(c1OC)OC)CN1CCN(CC1)C(c1ccc(cc1)F)c1ccc(cc1)F.Cl.Cl
• Canonical SMILES: COc1c(ccc(c1OC)OC)CN1CCN(CC1)C(c1ccc(cc1)F)c1ccc(cc1)F.Cl.Cl
• InChI: InChI=1S/C27H30F2N2O3.2ClH/c1-32-24-13-8-21(26(33-2)27(24)34-3)18-30-14-16-31(17-15-30)25(19-4-9-22(28)10-5-19)20-6-11-23(29)12-7-20;;/h4-13,25H,14-18H2,1-3H3;2*1H
• InChIKey: LOGVKVSFYBBUAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[bis(4-fluorophenyl)methyl]-4-[(2,3,4-trimethoxyphenyl)methyl]piperazine dihydrochloride
• IUPAC Traditional name: lomerizine dihydrochloride
• Synonyms: Lomerizine HCl; 1-[Bis(4-fluorophenyl)methyl]-4-[(2,3,4-trimethoxyphenyl)methyl]piperazine dihydrochloride; Lomerizine dihydrochloride

Database IDs

• CAS Number: 101477-54-7,101477-55-8(freebase); 101477-54-7
• MDL Number: MFCD01703867
• PubChem SID: 162249039
• PubChem CID: 122125

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.4496648
• LogD (pH = 7.4): 4.89666
• Log P: 5.0828657
• Molar Refractivity: 129.3686 cm^3
• Polarizability: 49.74478 Å^3
• Polar Surface Area: 34.17 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥30 mg/mL
• Apperance: white to tan powder

Safety Information

• RTECS: TK9189000
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-50
• Safety Statements: 61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H410
• GHS Precautionary statements: P273-P501
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: HCl
• Empirical Formula (Hill Notation): C27H30F2N2O3·2HCl

DETAILS

Sigma Aldrich - L6295

Biochem/physiol Actions
Lomerizine dihydrochloride is a voltage-dependent calcium channel blocker and selective cerebral vasodilator. It is one of the most selective calcium channel blockers for the CNS and cerebral arteries. It has been reported to inhibit both T-type and L-type Ca2+ currents in rat hippocampal CA1 pyramidal neurons, to prevent glutamate-induced neurotoxicity in rat hippocampal primary cell cultures, and to exhibit protective effects in animal models of migraine, ischemia and hypoxia. In Japan, lomerizine has been used as the first-line prophylactic drug for migraines.