2-(4-{3-[(9Z)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)(2H4)ethan-1-ol; butanedioic acid

• ChemBase ID: 179687
• Molecular Formular: C26H31ClN2O5S
• Molecular Mass: 519.05274
• Monoisotopic Mass: 518.16422078
• SMILES: C(CC(=O)O)C(=O)O.c1ccc2c(c1)/C(=C/CCN1CCN(CC1)CCO)/c1c(S2)ccc(c1)Cl
• Canonical SMILES: OC(=O)CCC(=O)O.OCCN1CCN(CC1)CC/C=C\1/c2ccccc2Sc2c1cc(Cl)cc2
• InChI: InChI=1S/C22H25ClN2OS.C4H6O4/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;5-3(6)1-2-4(7)8/h1-2,4-8,16,26H,3,9-15H2;1-2H2,(H,5,6)(H,7,8)/b18-5-
• InChIKey: KUEAHHOXAMWWOW-CVIBNLPVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{3-[(9Z)-2-chloro-9H-thioxanthen-9-ylidene]propyl}piperazin-1-yl)(^2H₄)ethan-1-ol; butanedioic acid
• IUPAC Traditional name: 2-(4-{3-[(9Z)-2-chlorothioxanthen-9-ylidene]propyl}piperazin-1-yl)(^2H₄)ethanol; succinic acid
• Synonyms: 4-[(3Z)-3-(2-Chloro-9H-thioxanthen-9-ylidene)propyl]-1-piperazineethanol-d4 Succinate; (Z)-Clopenthixol-d4 Succinate; Cisordinol-d4; Succinate Clopixol-d4 Succinate; cis-(Z)-Clopenthixol-d4 Succinate; cis-Clopenthixol-d4 Succinate; α-Clopenthixol-d4 Succinate; Zuclopenthixol-d4 Succinate Salt

Database IDs

• PubChem SID: 164235597
• PubChem CID: 71753041

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: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Pale Yellow Solid
• Melting Point: 49-51°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - Z701502

The labelled cis(Z)-form of Clopenthixol. Thioxanthene neuroleptic. Antipsychotic.

REFERENCES

• Sabbe, B., et al.: J. Psychiatr. Res., 30, 295 (1996)
• Riley, E., et al.: Schizophr. Res., 43, 47 (1996)
• Green, M., et al.: Biol. Psychiatry., 51, 972 (1996)
• Morrens, M., et al.: J. Clin. Psychopharmacol., 27, 15 (1996)