2-(4-{3-[(9E)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)(2H4)ethan-1-ol; [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methanesulfonic acid

• ChemBase ID: 164899
• Molecular Formular: C32H41ClN2O5S2
• Molecular Mass: 633.26134
• Monoisotopic Mass: 632.2145421
• SMILES: c1(ccc2c(c1)/C(=C/CCN1CCN(CC1)CCO)/c1c(S2)cccc1)Cl.C1[C@H]2CC(=O)[C@@](C1)(C2(C)C)CS(=O)(=O)O
• Canonical SMILES: O=C1C[C@H]2C([C@@]1(CC2)CS(=O)(=O)O)(C)C.OCCN1CCN(CC1)CC/C=C/1\c2ccccc2Sc2c1cc(Cl)cc2
• InChI: InChI=1S/C22H25ClN2OS.C10H16O4S/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26;1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h1-2,4-8,16,26H,3,9-15H2;7H,3-6H2,1-2H3,(H,12,13,14)/b18-5+;/t;7-,10-/m.0/s1
• InChIKey: OCUWZMAIQUFIER-QDJAPJFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{3-[(9E)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)(^2H₄)ethan-1-ol; [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methanesulfonic acid
• IUPAC Traditional name: (S)-camphorsulfonic acid; 2-(4-{3-[(9E)-2-chlorothioxanthen-9-ylidene]propyl}piperazin-1-yl)(^2H₄)ethanol
• Synonyms: 4-[(3E)-3-(2-Chloro-9H-thioxanthen-9-ylidene)propyl]-1-piperazineethanol-d4 (-)-10-Camphorsulfonic Acid Salt; (E)-Clopenthixol-d4 (-)-10-Camphorsulfonic Acid Salt; β-Clopenthixol-d4 (-)-10-Camphorsulfonic Acid Salt; trans-Clopenthixol-d4 (-)-10-Camphorsulfonic Acid Salt

Database IDs

• PubChem SID: 162259033
• PubChem CID: 71314944

CALCULATED PROPERTIES

• Acid pKa: 15.593099
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.396457
• LogD (pH = 7.4): 3.1579008
• Log P: 4.222984
• Molar Refractivity: 127.0003 cm^3
• Polarizability: 45.285892 Å^3
• Polar Surface Area: 26.71 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Ethanol; Methanol Thetrahydrofuran
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - C587192

The trans isomer of Clopenthixol, which exhibits similar pharmacological properties with its cis-isomer, Zuclopenthixol, less anti-dopaminergic effects.

REFERENCES

• Pajeva, I., et al.: J. Med. Chem., 41, 1815 (1993)
• Varga, A., et al.: Anticancer Res., 21, 2709 (1993)
• Leysen, J., et al.: Psychopharmacol., 110, 27 (1993)