Eltoprazine

Base Information

• Chemical Name: Eltoprazine
• CAS No.: 98224-03-4
• Molecular Formula: C12H16N2O2
• Molecular Weight: 220.271
• Hs Code.: 2934999090
• European Community (EC) Number: 872-479-1
• UNII: 510M006KO6
• DSSTox Substance ID: DTXSID5048425
• Nikkaji Number: J258.510C
• Wikipedia: Eltoprazine
• Wikidata: Q5367896
• NCI Thesaurus Code: C73286
• Metabolomics Workbench ID: 153781
• ChEMBL ID: CHEMBL282614
• Mol file: 98224-03-4.mol

Synonyms:1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine;DU 28853;DU-28853;eltoprazine;eltoprazine hydrochloride;piperazine, 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-, hydrochloride

Chemical Property of Eltoprazine

Chemical Property:

• Vapor Pressure: 4.13E-06mmHg at 25°C
• Boiling Point: 384.3°Cat760mmHg
• Flash Point: 186.2°C
• PSA: 33.73000
• Density: 1.18g/cm³
• LogP: 1.26120
• Storage Temp.: Store at RT
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 220.121177757
• Heavy Atom Count: 16
• Complexity: 231

Purity/Quality:

99%, ^*data from raw suppliers

Eltoprazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1)C2=C3C(=CC=C2)OCCO3
• Recent ClinicalTrials: Effects of Eltoprazine on Cognitive Impairment Associated With Schizophrenia (CIAS) in Adults
• Recent EU Clinical Trials: Phase 2, multicenter, randomized, double-blind, placebo-controlled, four-period cross-over, dose-range finding study to evaluate the safety, tolerability and efficacy of Eltoprazine in the treatment of levodopa induced dyskinesia in patients with Parkinson's disease.
• Uses: Eltoprazine is a partial agonist at SR-1 and SR-2C. Also, it is a 5-HT1A/1B receptor agonist.

Technology Process of Eltoprazine

There total 8 articles about Eltoprazine 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: 100.0%

→ eltoprazine (98224-03-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 1.33333h; Inert atmosphere;

Reference yield: 84.0%

bis-(2-chloroethyl)amine hydrochloride (821-48-7) + 1,4-benzodioxan-5-amine (16081-45-1) → eltoprazine (98224-03-4)

Guidance literature:

In chlorobenzene; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.1c04135

Reference yield: 59.0%

piperazine (110-85-0) + 5-bromo-2,3-dihydrobenzo[1,4]dioxin (58328-39-5) → eltoprazine (98224-03-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 100 ℃; for 4h; Sealed tube;

DOI:10.1021/acs.jmedchem.6b01208

upstream raw materials:

bis-(2-chloroethyl)amine hydrochloride

1,4-benzodioxan-5-amine

5-bromo-2,3-dihydrobenzo[1,4]dioxin

2,3-dihydro-1,4-benzodioxine-5-carboxylic acid

Downstream raw materials:

1-[3-(2-Chloro-phenoxy)-propyl]-4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazine, Oxalate

1-[1,4-benzodioxan-5-yl]-4-[3,4-dichlorophenylthiomethylcarbonyl]piperazine

3-amino-4-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-2-methyl-1-phenyl-3-pyrazolin-5-one

5-amino-4-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-3-cyclopropyl-1-phenylpyrazole

Refernces

• 1、 Jung, Woo-Ok,Yoo, Minjin,Migliozzi, Madyson M.,Zbieg, Jason R.,Stivala, Craig E.,Krische, Michael J.. "Regio- And Enantioselective Iridium-Catalyzed Amination of Alkyl-Substituted Allylic Acetates with Secondary Amines". supporting information. p. 441 - 445. Retrieved 2021/12/27.
• 2、 Chen, Xin,McCorvy, John D.,Fischer, Matthew G.,Butler, Kyle V.,Shen, Yudao,Roth, Bryan L.,Jin, Jian. "Discovery of G Protein-Biased D2 Dopamine Receptor Partial Agonists". . p. 10601 - 10618. Retrieved 2016/12/16.