6-chloro-10-(piperazin-1-yl)-2,9-diazatricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaene

• ChemBase ID: 126913
• Molecular Formular: C17H17ClN4
• Molecular Mass: 312.79668
• Monoisotopic Mass: 312.11417424
• SMILES: Clc1ccc2Nc3ccccc3C(=Nc2c1)N1CCNCC1
• Canonical SMILES: Clc1ccc2c(c1)N=C(N1CCNCC1)c1c(N2)cccc1
• InChI: InChI=1S/C17H17ClN4/c18-12-5-6-15-16(11-12)21-17(22-9-7-19-8-10-22)13-3-1-2-4-14(13)20-15/h1-6,11,19-20H,7-10H2
• InChIKey: JNNOSTQEZICQQP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-10-(piperazin-1-yl)-2,9-diazatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3,5,7,9,11,13-heptaene; 6-chloro-10-(piperazin-1-yl)-2,9-diazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene
• IUPAC Traditional name: NDMC; 6-chloro-10-(piperazin-1-yl)-2,9-diazatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene
• Synonyms: Desmethylclozapine; 8-Chloro-11-(1-piperazinyl)-5H-dibenzo[B,E][1,4]diazepine; N-Desmethyl Clozapine; 8-Chloro-11-piperazinyl-5H-dibenzo[b,e][1,4]diazepine; Norclozapine; Normethylclozapine; N-Desmethylclozapine

Database IDs

• CAS Number: 6104-71-8
• MDL Number: MFCD00210189
• PubChem SID: 24893957; 162221239
• PubChem CID: 2820
• CHEMBL: 845
• Chemspider ID: 14126465
• Wikipedia Title: Desmethylclozapine

CALCULATED PROPERTIES

• Acid pKa: 15.900137
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.02458695
• LogD (pH = 7.4): 1.5816934
• Log P: 3.017193
• Molar Refractivity: 92.0618 cm^3
• Polarizability: 34.018467 Å^3
• Polar Surface Area: 39.66 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol
• Apperance: Yellow Solid
• Melting Point: >120°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/22-36/37/38
• Safety Statements: 22-36-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H332-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Uncontrolled
• Gene Information: human ... KCNH1(3756)

DETAILS

Sigma Aldrich - D5676

Biochem/physiol Actions
Major metabolite of clozapine; potent 5-HT2 serotonin receptor antagonist and a ligand for the cloned 5-HT6 and 5-HT7 serotonin receptors. Also an allosteric potentiator of M1 muscarinic receptors.

Toronto Research Chemicals - D292000

A major metabolite of Clozapine (C587500). A potent and selective 5-HT2C serotonin receptor antogonist.

REFERENCES

• Kuoppamaki, M. et al.: Eur. J. Pharm. Mol. Pharm. Sect., 245, 179 (1993)
• Olessen, O.V., et al.: J. Chromatog., 622, 39 (1993)
• Pirmohamed, M., et al.: J. Pharmacol. Exp. Ther., 272, 984 (1995)