4-(3-chlorophenyl)-1-(3-{3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propyl)piperazin-1-ium-1-olate

• ChemBase ID: 178834
• Molecular Formular: C19H22ClN5O2
• Molecular Mass: 387.86328
• Monoisotopic Mass: 387.14620265
• SMILES: C1[N+](CCN(C1)c1cccc(c1)Cl)(CCCn1nc2n(c1=O)cccc2)[O-]
• Canonical SMILES: Clc1cccc(c1)N1CC[N+](CC1)([O-])CCCn1nc2n(c1=O)cccc2
• InChI: InChI=1S/C19H22ClN5O2/c20-16-5-3-6-17(15-16)22-10-13-25(27,14-11-22)12-4-9-24-19(26)23-8-2-1-7-18(23)21-24/h1-3,5-8,15H,4,9-14H2
• InChIKey: WPWLJYFNNKOAFU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(3-chlorophenyl)-1-(3-{3-oxo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propyl)piperazin-1-ium-1-olate
• IUPAC Traditional name: 4-(3-chlorophenyl)-1-(3-{3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-yl}propyl)piperazin-1-ium-1-olate
• Synonyms: 2-[3-[4-(3-Chlorophenyl)-1-oxido-1-piperazinyl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one; Trazodone N-Oxide

Database IDs

• CAS Number: 55290-68-1
• PubChem SID: 164234744
• PubChem CID: 46783124

CALCULATED PROPERTIES

• Acid pKa: 19.807756
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.007445
• LogD (pH = 7.4): 2.0074809
• Log P: 2.0074813
• Molar Refractivity: 107.9245 cm^3
• Polarizability: 39.37766 Å^3
• Polar Surface Area: 66.03 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 124-130°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T718510

Trazodone N-Oxide is a metabolite of Trazodone-HCl (T718500). Trazodone impurity A.

REFERENCES

• Garattini, S., et al.: Biochem. Pharmacol., 25, 13 (1976)
• Jauch, R., et al.: Arzneim.-Forsch., 26, 2084 (1976)