1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-ethyl-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one hydrochloride

• ChemBase ID: 154195
• Molecular Formular: C25H33Cl2N5O2
• Molecular Mass: 506.46782
• Monoisotopic Mass: 505.20113068
• SMILES: CCc1nn(c(=O)n1CCOc1ccccc1)CCCN1CCN(CC1)c1cccc(c1)Cl.Cl
• Canonical SMILES: CCc1nn(c(=O)n1CCOc1ccccc1)CCCN1CCN(CC1)c1cccc(c1)Cl.Cl
• InChI: InChI=1S/C25H32ClN5O2.ClH/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22;/h3-6,8-11,20H,2,7,12-19H2,1H3;1H
• InChIKey: DYCKFEBIOUQECE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3-ethyl-4-(2-phenoxyethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one hydrochloride
• IUPAC Traditional name: nefazodone hydrochloride
• Synonyms: 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl- 2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one hydrochloride; BMY-13754; MJ-13754-1; Serzone; Nefazodone hydrochloride; 2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one Hydrochloride; BMY 13754; BMY 13754-1; Dutonin; MJ 13754-1; Serazone; Nefazodone Hydrochloride; 1-(3-(4-(3-Chlorophenyl)piperazin-1-yl)propyl)-3-ethyl-4-(2-phenoxyethyl)-1H-1,2,4-triazol-5(4H)-one hydrochloride

Database IDs

• CAS Number: 82752-99-6
• MDL Number: MFCD00935760
• PubChem SID: 24724551; 162248334
• PubChem CID: 54911

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.0591223
• LogD (pH = 7.4): 4.4805546
• Log P: 4.652968
• Molar Refractivity: 132.376 cm^3
• Polarizability: 50.688282 Å^3
• Polar Surface Area: 51.62 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥10 mg/mL; H2O: insoluble; Methanol
• Apperance: white solid; White Solid
• Melting Point: 180-182°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (HPLC); 98%
• Empirical Formula (Hill Notation): C25H32ClN5O2 · HCl

DETAILS

Sigma Aldrich - N5536

Biochem/physiol Actions
Novel antidepressant; mixed 5-HT2A serotonin receptor antagonist/serotonin uptake inhibitor.

Toronto Research Chemicals - N389100

A selective serotonin 5-HT2 receptor antagonist. A novel antidepressant that shows no cardiac toxicity or anticholinergic activity common with tricyclic antidepressants.

REFERENCES

• Eison, A.S., et al.: Psychopharmacol. Bull., 26, 311 (1990)
• Keller, M.B., et al.: N. Engl. J. Med., 342, 1462 (2000)