Perospirone

Base Information

• Chemical Name: Perospirone
• CAS No.: 150915-41-6
• Molecular Formula: C₂₃H₃₀N₄O₂S
• Molecular Weight: 426.583
• European Community (EC) Number: 889-491-8
• UNII: N303OK87DT
• DSSTox Substance ID: DTXSID2048163
• Nikkaji Number: J354.051K
• Wikipedia: Perospirone
• Wikidata: Q6590349
• NCI Thesaurus Code: C66358
• Pharos Ligand ID: VRSJNACDYAFG
• Metabolomics Workbench ID: 152004
• ChEMBL ID: CHEMBL1472975
• Mol file: 150915-41-6.mol

Synonyms:2-(4-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)butyl)hexahydro-1H-isoindole-1,3-(2H)-dione;perospirone;SM 9018;SM-9018

Chemical Property of Perospirone

Chemical Property:

• Appearance/Colour: White powder
• Refractive Index: 1.702
• PSA: 84.99000
• LogP: 3.31450
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 426.20894739
• Heavy Atom Count: 30
• Complexity: 615

Purity/Quality:

99% ^*data from raw suppliers

Perospirone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C(C1)C(=O)N(C2=O)CCCCN3CCN(CC3)C4=NSC5=CC=CC=C54
• Isomeric SMILES: C1CC[C@H]2[C@@H](C1)C(=O)N(C2=O)CCCCN3CCN(CC3)C4=NSC5=CC=CC=C54
• Recent NIPH Clinical Trials: A randomized clinical trial of delirium treatment
• Description: Perospirone hydrochloride was launched in Japan as a new treatment of schizophrenia and other psychoses. This structurally-related analog of ziprasidone can be classically prepared by alkylation of 1-(3-benzisothiazolyl)-piperazine with the appropriate N- (chlorobutyl)-succinimide. As a result of an in vitro determination of its binding profile, perospirone demonstrated a high affinity for 5-HT2, 5-HT1A and D2 receptors as well as a significant but lower affinity for DI and al receptors. Interestingly, these differential effects on neurotransmitters with a high in vivo occupancy of 5-HT2A receptors with lower D2 occupancy seems to provide this new agent with a significantly lower propensity for the development of extrapyramidal symptoms (EPS) and tardive schizophrenia, the main sideeffects associated with classical antipsychotic therapy. Furthermore, perospirone exhibited anxiolytic-like effects in animal models. A long-term clinical trial (> 6 months) in a group of patients suffering from schizophrenia demonstrated the efficacy of perospirone over placebo for the treatment of the positive, negative and general symptoms of schizophrenia at doses of 12 mg to 96 mg t.i.d.

Technology Process of Perospirone

There total 3 articles about Perospirone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.9%

3-(1-piperazinyl)-1,2-benzisothiazole (87691-87-0) + N-(4-bromobutyl)-1,2-cis-cyclohexanedicarboximide → Perospirone (150915-41-6)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 90 - 100 ℃; for 7h;

DOI:10.1248/cpb.43.2139

Reference yield:

3-chloro-1,2-benzisothiazole (7716-66-7) → Perospirone (150915-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 56.4 percent / 12 h / 120 °C

2: 84.9 percent / K₂CO₃, KI / dimethylformamide / 7 h / 90 - 100 °C

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.43.2139

Reference yield:

→ Perospirone (150915-41-6)

Guidance literature:

upstream raw materials:

3-(1-piperazinyl)-1,2-benzisothiazole

3-chloro-1,2-benzisothiazole

Refernces

• 1、 Ishizumi,Kojima,Antoku,Saji,Yoshigi. "Succinimide derivatives. II. Synthesis and antipsychotic activity of N- [4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]1,2-cis- cyclohexanedicarboximide (SM-9018) and related compounds". . p. 2139 - 2151. Retrieved 2007/10/03.