Zopiclone

Base Information

• Chemical Name: Zopiclone
• CAS No.: 43200-80-2
• Deprecated CAS: 138680-07-6
• Molecular Formula: C17H17ClH6O3
• Molecular Weight: 388.813
• Hs Code.: 29339900
• European Community (EC) Number: 256-138-9
• NSC Number: 758463
• UNII: 03A5ORL08Q
• DSSTox Substance ID: DTXSID4041155
• Nikkaji Number: J16.885H
• Wikipedia: Zopiclone
• Wikidata: Q220426
• NCI Thesaurus Code: C80279
• Pharos Ligand ID: UFYBVMZGZNAD
• Metabolomics Workbench ID: 144685
• ChEMBL ID: CHEMBL135400
• Mol file: 43200-80-2.mol

Synonyms:6-(5-chloro-2-pyridyl)-6,7-dihydro- 7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methyl-1- piperazinecarboxylate;Imovane;Limovan;Nu-Zopiclone;Optidorm;ratio-Zopiclone;Rhovane;RP 27 267;Siaten;Somnosan;Ximovan;Zileze;Zimoclone;Zimovane;Zop;Zopi-Puren;Zopicalm;Zopicalma;zopiclodura;Zopiclon AbZ;Zopiclon AL;Zopiclon AZU;Zopiclon beta;Zopiclon Stada;Zopiclon TAD;zopiclon von ct;Zopiclon-neuraxpharm;Zopiclon-ratiopharm;Zopiclon-TEVA;zopiclone;Zopitan;Zorclone

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Chemical Property of Zopiclone

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 1.78E-13mmHg at 25°C
• Melting Point: 178 °C
• Boiling Point: 580.7 °C at 760 mmHg
• PKA: pKa ﹣1.5±0.1(10% ACN in aq. H2SO4 t = 25.0) (Uncertain)
• Flash Point: 305 °C
• PSA: 91.76000
• Density: 1.54 g/cm³
• LogP: 1.50880
• Storage Temp.: Store at RT
• Solubility.: DMSO: 2 mg/mL
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 388.1050661
• Heavy Atom Count: 27
• Complexity: 573

Purity/Quality:

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi,F
• Statements: 20/21/22-36/37/38-62-36-11
• Safety Statements: 26-36-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
• Recent ClinicalTrials: A Study to Investigate the Next-day Residual Effects of TS-142 in Healthy Elderly Subjects
• Recent EU Clinical Trials: Self-help program for hypnotics withdrawal in insomniac patients: A randomized controlled clinical trial.
• Recent NIPH Clinical Trials: Study of the effect of psychotrophics on cognitive function and driving performance including gene and fMRI analysis
• Description: Zopiclone is an agonist at the type A γ-aminobutyric acid (GABA) receptor. It is a non-benzodiazepine hypnotic which was first reviewed in Drugs in 1986 and it is indicated for short-term treatment of insomnia. Zopiclone has a relatively low propensity to cause residual clinical effects (such as difficulty in waking or reduced morning concentration). Zopiclone is an effective hypnotic agent with a short duration of action. Although it interacts with the benzodiazepine receptor complex, it is reported to have minimal effects on memory, little synergy with alcohol, and low abuse potential.
• Uses: antihyperammonemic,antineoplastic inhibits tyrosinase and prevents melanin formation used to whiten and lighten skin Cyclopyrrolone member of a family of non-benzodiazepine GABAA receptor agonists. This is a controlled substance (depressant) in the US but not in Canada. Sedative, hypnotic
• Therapeutic Function: Sedative, Hypnotic
• Clinical Use: Hypnotic
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: metabolism inhibited by erythromycin; concentration significantly reduced by rifampicin. Antipsychotics: enhanced sedative effects. Antivirals: concentration possibly increased by ritonavir.

Technology Process of Zopiclone

There total 9 articles about Zopiclone 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: 95.0%

4-methylpiperazine-1-carbonyl chloride monohydrochloride (55112-42-0) + 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one (43200-81-3,537036-14-9) → zopiclon (43200-80-2)

Guidance literature:

4-methylpiperazine-1-carbonyl chloride monohydrochloride; With triethylamine; In dichloromethane; at 5 ℃; for 0.416667h;

dmap; In dichloromethane; for 0.0166667 - 0.0333333h;

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one; In dichloromethane; at 20 ℃; for 7h; Product distribution / selectivity; Heating / reflux;

Reference yield: 89.0%

eszopiclone (138729-47-2) → zopiclon (43200-80-2)

Guidance literature:

With N,N,N',N'-tetramethylguanidine; In dimethyl sulfoxide; at 80 ℃; for 5h; Solvent; Temperature;

Reference yield: 82.0%

(-)-Zopiclone (138680-08-7) → zopiclon (43200-80-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In xylene; at 70 - 100 ℃; for 1.5h; Product distribution / selectivity;

upstream raw materials:

4-methylpiperazine-1-carbonyl chloride monohydrochloride

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

(-)-Zopiclone

4-methyl-piperazine-1-carbonyl chloride

Downstream raw materials:

eszopiclone

(+)-6-(5-chloro-2-pyridyl)-5-[(4-methyl-1-piperazinyl)-carbonyloxy]-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine di-p-toluyl-D-tartate

D(+)-O,O-dibenzoyl tartarate of zopiclone

eszopiclone di-p-toluoyl-L-tartaric acid salt

Refernces

• 1、 -. "A method for producing zopiclone". Paragraph 0029; 0030. . Retrieved 2017/01/05.
• 2、 -. "CRYSTALLINE POLYMOPHIC FORMS OF ZOPICLONE, PROCESSES FOR THEIR PREPARATION AND THEIR PHARMACEUTICAL COMPOSITIONS". Page/Page column 4. . Retrieved 2010/08/07.