Zopiclone

Zopiclone Basic information
Description References
Product Name:Zopiclone
Synonyms:4-Methyl-1-piperazinecarboxylic acid ester with 6-(5-chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one;6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylate;Amoban;Amovane;Imovance;oxo-5h-pyrrolo(3,4-b)pyrazin-5-ylester;RP-27267;Sopivan
CAS:43200-80-2
MF:C17H17ClN6O3
MW:388.81
EINECS:256-138-9
Product Categories:Isotopically Labeled Pharmaceutical Reference Standard;BUPHENYL;Intermediates & Fine Chemicals;Pharmaceuticals;GABA;Other APIs;Active Pharmaceutical Ingredients;Sedative, Hypnotic;Isotope Labeled Compounds
Mol File:43200-80-2.mol
Zopiclone Structure
Zopiclone Chemical Properties
Melting point 1780C
Boiling point 580.7±50.0 °C(Predicted)
density 1.1105 (estimate)
Fp 2℃
storage temp. Store at RT
solubility DMSO: 2 mg/mL
pkapKa ﹣1.5±0.1(10% ACN in aq. H2SO4 t = 25.0) (Uncertain)
form Solid
color White to Off-White
Stability:Hygroscopic
InChIKeyGBBSUAFBMRNDJC-UHFFFAOYSA-N
CAS DataBase Reference43200-80-2(CAS DataBase Reference)
NIST Chemistry ReferenceZopiclone(43200-80-2)
Safety Information
Hazard Codes Xn,Xi,F
Risk Statements 20/21/22-36/37/38-62-36-11
Safety Statements 26-36-36/37-16
RIDADR UN 1648 3 / PGII
WGK Germany 3
RTECS TL1425000
HS Code 29339900
Toxicitymouse,LD50,intramuscular,541mg/kg (541mg/kg),LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSIONBEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY),Oyo Yakuri. Pharmacometrics. Vol. 26, Pg. 935, 1983.
Zopiclone Usage And Synthesis
DescriptionZopiclone 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).
References[1] Stuart Noble, Heather D. Langtry and Harriet M. Lamb, Drugs, 1998, vol. 55, 277-302
[2] G. Hajak, W. E. Müller, H. U. Wittchen, D. Pittrow, W. Kirch, Abuse and dependence potential for the non-benzodiazepine hypnotics zolpidem and zopiclone: a review of case reports and epidemiological data, Addiction, 2003, vol. 98, 1371-1378
DescriptionZopiclone 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.
Chemical PropertiesCrystalline Solid
OriginatorRhone-Poulenc (France)
Usesantihyperammonemic,antineoplastic
Usesinhibits tyrosinase and prevents melanin formation used to whiten and lighten skin
UsesCyclopyrrolone 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
DefinitionChEBI: A pyrrolo[3,4-b]pyrazine compound having a 4-methylpiperazine-1-carboxyl group at the 5-position, a 5-chloropyridin-2-yl group at the 6-position and an oxo-substituent at the 7-position.
Manufacturing ProcessProducing of 6-(5-chloropyrid-2-yl)-5-(4-methylpiperazin-1-yl)-carbonyloxy-7- oxo-5,6-dihydropyrrolo[3,4-b]pyrazine by two methods.
1). A solution of 6-(5-chloropyrid-2-yl)-5-hydroxy-7-oxo-5,6- dihydropyrrolo[3,4-b]pyrazine (12.0 g) in anhydrous dimethylformamide (360 ml) is added to a suspension of sodium hydride (50% dispersion in mineral oil) (2.4 g) in anhydrous dimethylformamide (60 ml), whilst maintaining the temperature at about -10°C. When the evolution of gas has ceased, a solution of 1-chlorocarbonyl-4-methylpiperazine (8.1 g) in anhydrous dimethylformamide (20 ml) is added, whilst maintaining the temperature at about -10°C. The reaction mixture is stirred for a further 3 h whilst allowing it to heat up gradually to a temperature of about 20°C, and then it is poured into ice-water (1540 ml). The product which crystallizes is filtered off, washed with water (150 ml) and then with diisopropyl ether (100 ml). After drying, a product is obtained and is dissolved in ethyl acetate (600 ml). The solution obtained is filtered through silica gel (250.0 g). Elution is then carried out with ethyl acetate (3200 ml) followed by a mixture of ethyl acetate and methanol The eluates are combined and concentrated to dryness under reduced pressure. So 8.3 g of the 6-(5-chloropyrid-2-yl)-5-(4-methylpiperazin-1-yl)- carbonyloxy-7-oxo-5,6-dihydropyrrolo[3,4-b]pyrazine are obtained, melting point 178°C (recrystallisation from a mixture of acetonitrile and diisopropyl ether 1:1; 190 ml).
2). 1-Methylpiperazine (155.0 g) is added to a suspension of 6-(5-chloropyrid- 2-yl)-7-oxo-5-phenoxycarbonyloxy-5,6-dihydropyrrolo[3,4-b]pyrazine (194.0 g) in acetone (970 ml) cooled to a temperature of about 3°C. The reaction mixture is stirred for 3 h at a temperature of about 3°C and is then poured into water (5000 ml). The product which precipitates is filtered off and then washed with water (600 ml) and dried. This product is treated with methylene chloride (1100 ml) at a temperature of about 20°C. The insoluble material is filtered off and then the filtrate is washed with 1 N sodium hydroxide solution (3x200 ml) and with water (3x200 ml). The organic phase is treated with decolorizing charcoal (10.0 g), dried over potassium carbonate, filtered and then concentrated to dryness under reduced pressure. The oily residue obtained is dissolved in boiling acetonitrile (500 ml). The 101.0 g of 6-(5- chloropyrid-2-yl)-5-(4-methylpiperazin-l-yl)carbonyloxy-7-oxo-5,6- dihydropyrrolo[3,4-b]-pyrazine are obtained, melting point 178°C (washed with ice cold acetonitrile, 50 ml, and then crystallizes with diisopropyl ether, 50 ml).
Brand nameIMOVANE
Therapeutic FunctionSedative, Hypnotic
World Health Organization (WHO)Zopiclone was introduced as a sedative in 1985. It remains registered in several countries and the World Health Organization is not aware of any other country that has refused registration.
Clinical UseHypnotic
Drug interactionsPotentially 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.

MetabolismZopiclone is extensively metabolised in the liver via the cytochrome P450 isoenzyme CYP3A4 and, to a lesser extent, CYP2C8; the 2 major metabolites, the less active zopiclone N-oxide and the inactive N-desmethylzopiclone, are excreted mainly in the urine. About 50
% of a dose is converted by decarboxylation to inactive metabolites, which are partly eliminated via the lungs as carbon dioxide.
Piperacillin Methylparaben ZOPICLONE N-OXIDE,Zopiclone N-Oxide (Mixture of diastereomers) Methyl Zopiclone Zopiclone (S)-,(S)-(+)-ZOPICLONE N-Aminoethylpiperazine N-Methyl-2-pyrrolidone Bensulfuron methyl Parathion-methyl (S)-(+)-Zopiclone N-Oxid Polyvinylpyrrolidone Difluorochloromethane METHYL-2-PYRROLIDONE Kresoxim-methyl Thiophanate-methyl Methyl acrylate Methyl bromide

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