Зопиклон , Zopiclone, زوبيكلون , 佐匹克隆

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Zopiclone structure.svg


1-Piperazinecarboxylic acid, 4-methyl-, 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester
256-138-9 [EINECS]
43200-80-2 [RN]

Structural formula

UV- Spectrum

Conditions : Concentration – 1 mg / 100 ml
The solvent designation schedule methanol


0.1М HCl

0.1M NaOH

maximum absorption There


303 nm 304 nm 277 nm

237 nm

362 364 199


e 10500 10500 5800


IR – spectrum

Wavelength (μm)
Wave number (cm -1 )

MASS spectrum

10 largest peaks:
Peak 42 56 99 112 139 143 217 245 246 247
Value 155 231 280 283 209 999 279 719 156 250


  • UV and IR Spectra. H.-W. Dibbern, R.M. Muller, E. Wirbitzki, 2002 ECV

  • NIST/EPA/NIH Mass Spectral Library 2008

  • Handbook of Organic Compounds. NIR, IR, Raman, and UV-Vis Spectra Featuring Polymers and Surfactants, Jr., Jerry Workman. Academic Press, 2000.

  • Handbook of ultraviolet and visible absorption spectra of organic compounds, K. Hirayama. Plenum Press Data Division, 1967.

Brief background information

Salt ATC formula MM CASE
N05CF01 17 H 17 ClN 6 O 3 388.82 g / mol 43200-80-2


  • sedative

  • hypnotic

Classes substance

  • chlorine compounds

    • oxo

      • Esters of 1-piperazinecarboxylate

        • pyridines

          • Pirrolo [3,4-b] piraziny

Synthesis Way

Синтез a)

Trade names

country Tradename Manufacturer
Germany Optydorm DOLORGIET
Somnosan Hormos
Ksimovan Sanofi-Aventis
Zopi-cigar Actavis
various generic drugs
France imovane SanofiAventis
Noktireks Sanofi-Synthélabo
United Kingdom Snowman SanofiAventis
Italy imovane SanofiAventis
tion THERE
Japan Amoʙan Sanofi-Aventis; Chugai; Mitsubishi
Ukraine imovane Sanofi Winthrop Indastria, France
various generic drugs


  • coated tablets 7.5 mg;

  • Tablets 7.5 mg, 10 mg


  • DOS 2 300 491 (Rhône-Poulenc; appl. 5.1.1973; F-prior. 7.1.1972, 9.9.1972).

  • US 3 862 149 (Rhône-Poulenc; 21.1.1975; F-prior. 7.1.1972, 9.9.1972).

Two major zopiclone metabolites.

Two major zopiclone metabolites.

CAS Registry No.: 43200-80-2
Molecular Formula: C17H17ClN6O3 Molecular Weight: 388.8
Compound Name:

1-piperazinecarboxylic acid, 4-methyl-, 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl ester

4-methyl-1-piperazinecarboxylic acid 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)-pyrazin-5-yl ester

4-methyl-1-piperazinecarboxylic acid-6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)-pyrazin-5-yl ester

6-(5-chloro-2-pyridyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methyl-1-piperazinecarboxylate


6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methylpiperazine-1-carboxylate

amoban (R)


Zopiclone (Imovance), 4-methyl-1-piperzinecarboxylic acid 6-(5-chloro-2- pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester (Figure 1) is one of the non benzodiazepine sedative-hypnotics of the cyclopyrrolone class, sold by Rhone-Poulene Company in France since 1987. Although structurally unrelated to benzodiazepines, its pharmacological profile is similar, exhibiting sedative-hypnotic, anxiolytic, myorelaxant, and anticonvulsant activity.[1] Other than the first generation barbiturates and the second-generation benzodiazepines, zopiclone, which is widely used in Europe as well as other regions worldwide,[2,3] as a representative of the third generation sedative-hypnotic drugs, has been shown to be free from residual effects on performance and psychological function the day after intake and from the risks of accumulation because of its short elimination half-life (3.5 to 6.5 hours).[3,4] It is indicated for the short term treatment of insomnia, transient, situational or chronic insomnia, and insomnia secondary to psychiatric disturbances.[3]

REFERENCES 1. Mann, K.; Bauer, H.; Hiemke, C.; Ro¨schke, J.; Wetzel, H.; Benkert, O. Acute, subchronic and discontinuation effects of zopiclone on sleep EEG and nocturnal melatonin secretion. Eur. Neuropsychopharm. 1996, 6 (3), 163– 168. Structure Elucidation of Sedative-Hypnotic Zopiclone 359 Downloaded by [Dalhousie University] at 22:10 19 December 2012

2. Le´ger, D.; Janus, C.; Pellois, A.; Quera-Salva, M.A.; Dreyfus, J.P. Sleep, morning alertness and quality of life in subjects treated with zopiclone and in good sleepers. study comparing 167 patients and 381 good sleepers. Eur. Psychiat. 1995, 10 (973) Suppl. 3, 99s – 102s.

3. Piperaki, S.; Parissi-Poulou, M. Enantiomeric separation of zopiclone, its metabolites and products of degradation on a b-cyclodextrin bonded phase. J. Chromatogr. A 1996, 729 (1 – 2), 19 – 28

Spectral Data Analyses and Structure Elucidation of Sedative‐Hypnotic Zopiclone

Pages 349-360 | Received 10 Sep 2006, Accepted 18 Oct 2006, Published online: 13 Oct 2010

Zopiclone structure.svg
Zopiclone ball-and-stick.png
Systematic (IUPAC) name

(RS)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate

Clinical data
Trade names Imovane, Zimovane
AHFS/Drugs.com International Drug Names
  • AU: C
  • US: C (Risk not ruled out)
Routes of
Oral tablets, 3.75 mg (UK), 5 or 7.5 mg
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: Class C (POM)
  • US: Schedule IV
Pharmacokinetic data
Bioavailability 75-80%[1]
Protein binding 52–59%
Metabolism Hepatic through CYP3A4and CYP2E1
Biological half-life ~5 hours (3.5–6.5 hours)

~7–9 hours for over 65

Excretion Urine (80%)
CAS Number 43200-80-2 Yes
ATC code N05CF01 (WHO)
PubChem CID 5735
DrugBank DB01198 Yes
ChemSpider 5533 Yes
KEGG D01372 Yes
ChEBI CHEBI:32315 Yes
Chemical data
Formula C17H17ClN6O3
Molar mass 388.808 g/mol
3D model (Jmol) Interactive image


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