| Identification | Back Directory | [Name]
11-(4-methyl-1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepine | [CAS]
1977-07-7 | [Synonyms]
Dechloroclozapine
Dopamine serotonin antagonist-1
11-(4-methyl-1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepine
11-(4-Methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine
5H-Dibenzo[b,e][1,4]diazepine, 11-(4-methyl-1-piperazinyl)- | [Molecular Formula]
C18H20N4 | [MDL Number]
MFCD01730958 | [MOL File]
1977-07-7.mol | [Molecular Weight]
292.38 |
| Chemical Properties | Back Directory | [Boiling point ]
457.5±55.0 °C(Predicted) | [density ]
1.22±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
DMSO : ≥ 83.3 mg/mL (284.90 mM) | [form ]
solid | [pka]
7.82±0.20(Predicted) | [color ]
Yellow |
| Hazard Information | Back Directory | [Biological Activity]
Deschloroclozapine is a potent, high-affinity, selective, metabolically stable agonist of muscarinic-based DREADDs. | [Synthesis]
General procedure for the synthesis of 11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,E][1,4]diazepin-11-one from N-methylpiperazine and 5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one: 5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one (105 mg , 0.5 mmol) was placed in a 50 mL round bottom flask. N,N-dimethylaniline (36.3 mg, 0.3 mmol) was added sequentially. An appropriate amount of super-dry trichlorophosphorus and a magnetic stirrer were added and the mixture was stirred under reflux conditions for 12 h at 130°C under nitrogen protection. Upon completion of the reaction, the excess phosphorous trichloride was removed by distillation. Subsequently, the reaction was terminated by adding an appropriate amount of N-methylpiperazine and continued stirring for 12 hours. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was extracted with ethyl acetate (3 x 70 mL) and washed sequentially with water. The organic layers were combined and dried by adding anhydrous Na2SO4. After filtration, the residue was concentrated. Purification by column chromatography (eluent: dichloromethane/methanol = 25:1) afforded 110 mg of the target product 11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,E][1,4]diazepine in 75% yield. | [in vitro]
Deschloroclozapine has greater potencies for DREADDs than previous agonists in vitro. Deschloroclozapine is a potent agonist for hM 3 Dq with an EC 50 =0.13 nM. Deschloroclozapine is also a potent agonist for hM 4 Di with an EC 50 =0.081 nM.
Deschloroclozapine is a potent and selective agonist for hM 3 Dq and hM 4 Di, it does not display significant agonistic activity for any of the 318 tests wild-type GPCRs at <10 nM. b> | [target]
Ki: 6.3 nM (hM 3 Dq), 4.2 nM (hM 4 Di) | [storage]
Store at -20°C | [References]
[1] Patent: CN108586364, 2018, A. Location in patent: Paragraph 0150; 0151; 0152 |
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