4-{6-chloro-2,9-diazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl}-1-methylpiperazin-1-ium-1-olate

• ChemBase ID: 134300
• Molecular Formular: C18H19ClN4O
• Molecular Mass: 342.82266
• Monoisotopic Mass: 342.12473893
• SMILES: C[N+]1(CCN(CC1)C1=Nc2cc(ccc2Nc2c1cccc2)Cl)[O-]
• Canonical SMILES: Clc1ccc2c(c1)N=C(N1CC[N+](CC1)([O-])C)c1c(N2)cccc1
• InChI: InChI=1S/C18H19ClN4O/c1-23(24)10-8-22(9-11-23)18-14-4-2-3-5-15(14)20-16-7-6-13(19)12-17(16)21-18/h2-7,12,20H,8-11H2,1H3
• InChIKey: OGUCZBIQSYYWEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{6-chloro-2,9-diazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl}-1-methylpiperazin-1-ium-1-olate; 4-{6-chloro-2,9-diazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-10-yl}-1-methylpiperazin-1-ium-1-olate
• IUPAC Traditional name: 4-{6-chloro-2,9-diazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,9,12,14-heptaen-10-yl}-1-methylpiperazin-1-ium-1-olate; 4-{6-chloro-2,9-diazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-10-yl}-1-methylpiperazin-1-ium-1-olate
• Synonyms: 8-Chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo[b,e](1,4)diazepine N-oxide; Clozapine N-oxide; 8-Chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo[b,e][1,4]diazepine N-Oxide; Clozapine N-Oxide

Database IDs

• CAS Number: 34233-69-7
• MDL Number: MFCD00210190
• PubChem SID: 24892276; 162228577
• PubChem CID: 2819

CALCULATED PROPERTIES

• Acid pKa: 15.899332
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.269063
• LogD (pH = 7.4): 2.2757795
• Log P: 2.2758658
• Molar Refractivity: 99.4014 cm^3
• Polarizability: 36.000393 Å^3
• Polar Surface Area: 54.51 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Ether
• Apperance: Yellow Solid
• Melting Point: 255-260°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: HP1760000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

DETAILS

Sigma Aldrich - C0832

Biochem/physiol Actions
5-HT2 serotonin receptor antagonist; major metabolite of clopazine that can be monitored by HPLC.

Toronto Research Chemicals - C587520

A 5-HT2 antagonist. A major metabolite of clozapine that can be monitored by HPLC. Possesses little or no activity towards serotonin receptors.

REFERENCES

• Lin, G., et al.: J. Pharm. Sci, 83, 1412 (1994, Roth, B.L., et al.: J. Pharmacol. Exp. Ther., 268, 1403 (1994)