ContaminantDB: Zopiclone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:36 UTC

Update Date

2026-03-31 19:06:59 UTC

Accession Number

CHEM002373

Identification

Common Name

Zopiclone

Class

Small Molecule

Description

Zopiclone is only found in individuals that have used or taken this drug. It is a novel hypnotic agent used in the treatment of insomnia. Its mechanism of action is based on modulating benzodiazepine receptors. In addition to zopiclone's benzodiazepine pharmacological properties it also has some barbiturate like properties. Zopiclone exerts its action by binding on the benzodiazepine receptor complex and modulation of the GABA_BZ receptor chloride channel macromolecular complex. Both zopiclone and benzodiazepines act indiscriminately at the benzodiazepine binding site on α1, α2, α3 and α5 GABA_A containing receptors as full agonists causing an enhancement of the inhibitory actions of GABA to produce the therapeutic (hypnotic and anxiolytic) and adverse effects of zopiclone.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amide
Amine
Drug
Ester
Ether
Hypnotic and Sedative
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Zopiclone	ChEBI
6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylate	ChEBI
Zopiclona	ChEBI
Zopiclonum	ChEBI
Amoban	Kegg
6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylic acid	Generator
Limovan	HMDB
Nu-zopiclone	HMDB
Zileze	HMDB
Zimovane	HMDB
Zopicalm	HMDB
Zopiclon al	HMDB
Zopiclon stada	HMDB
Zopiclon tad	HMDB
Zopiclon-teva	HMDB
Zopiclon-neuraxpharm	HMDB
Zorclone	HMDB
Ratio-zopiclone	HMDB
Siaten	HMDB
Somnosan	HMDB
Ximovan	HMDB
Zopiclon azu	HMDB
Zopiclon abz	HMDB
Zopiclodura	HMDB
Rhovane	HMDB
Zimoclone	HMDB
Zopiclon beta	HMDB
Zopitan	HMDB
6-(5-Chloro-2-pyridyl)-6,7-dihydro- 7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl 4-methyl-1- piperazinecarboxylate	HMDB
Imovane	HMDB
Optidorm	HMDB
Zop	HMDB
Zopi-puren	HMDB
Zopicalma	HMDB
Zopiclon-ratiopharm	HMDB
Zopiclon von CT	HMDB

Chemical Formula

C₁₇H₁₇ClN₆O₃

Average Molecular Mass

388.808 g/mol

Monoisotopic Mass

388.105 g/mol

CAS Registry Number

43200-80-2

IUPAC Name

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

Traditional Name

zopiclone

SMILES

CN1CCN(CC1)C(=O)OC1N(C(=O)C2=NC=CN=C12)C1=NC=C(Cl)C=C1

InChI Identifier

InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3

InChI Key

GBBSUAFBMRNDJC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as thienothiazines. These are heterocyclic compounds containing a thiophene ring fused to a thiazine. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Thiazine is a 6-membered ring consisting of four carbon, one nitrogen and one sulfur atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thienothiazines

Sub Class

Not Available

Direct Parent

Thienothiazines

Alternative Parents

Substituents

Thienothiazine
2,3,5-trisubstituted thiophene
Aralkylamine
Ortho-thiazine
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Heteroaromatic compound
Aminosulfonyl compound
Thiophene
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Azacycle
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:41212 )
thienothiazine (CHEBI:41212 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	178°C
Boiling Point	Not Available
Solubility	0.151 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
logP	0.97	ALOGPS
logP	0.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.04	ChemAxon
pKa (Strongest Basic)	6.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	91.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.89 m³·mol⁻¹	ChemAxon
Polarizability	38.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05bb-9212000000-b3e4c2874ff86d2544e1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kb-0090000000-9d80e08080f406848221	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0092000000-977d45f9a516242be80f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0090000000-397a508c11f66c161327	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014j-0090000000-abc6a676659114a83d08	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0790000000-74d7c73e854e61700433	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00lr-0920000000-2c17f6282d1031cb4d50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-c0f92aba9374337ff737	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-003r-5900000000-46755df8b5cfb7f46bf9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-9300000000-091d5434bc674d5bf9a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-9000000000-87365fa01fb0854897ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-014j-0090000000-10c3fa2d80a8abbefd55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0090000000-1867bce03fb895923ceb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-014i-0790000000-462830e768acf8704d81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00lr-0920000000-6c00112af341c07aba1b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0002-0092000000-b9948d590c2d56a477e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - -1V, Positive	splash10-00kb-0090000000-66a3d681838796c245d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-58198ad5b8e6fb5075fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-5917000000-fed7a3a68ceccd2f26be	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ac0-9000000000-ef1623aed48bd5073d7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0309000000-e2a958d8569e44198c06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1901000000-d74484c0d625330ab7cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9510000000-15dec99e5a9537957558	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-8fbf9af9d2708ba6bc8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-0049000000-0d0bcaed2a13fc359e64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-2695000000-54c5cabfed200237305e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0007-6950000000-c1583a92e3cbc5066186	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Rapidly absorbed following oral administration.

Mechanism of Toxicity

Zopiclone exerts its action by binding on the benzodiazepine receptor complex and modulation of the GABA_BZ receptor chloride channel macromolecular complex. Both zopiclone and benzodiazepines act indiscriminately at the benzodiazepine binding site on alpha1, alpha2, alpha3 and alpha5 GABAA containing receptors as full agonists causing an enhancement of the inhibitory actions of GABA to produce the therapeutic (hypnotic and anxiolytic) and adverse effects of zopiclone.

Metabolism

Extensively metabolized in the liver via decarboxylation (major pathway), demethylation, and side chain oxidation. Metabolites include an N-oxide derivative (weakly active; approximately 12% of a dose) and an N-desmethyl metabolite (inactive; approximately 16%). Approximately 50% of a dose is converted to other inactive metabolites via decarboxylation. Hepatic microsomal enzymes are apparently not involved in zopiclone clearance. Half Life: Elimination half life is approximately 5 hours (range 3.8 to 6.5 hours) and is prolonged to 11.9 hours in patients with hepatic insufficiency.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the short-term treatment of insomnia.

Minimum Risk Level

Not Available

Health Effects

They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.

Symptoms

Rare individual instances of fatal outcomes following overdose with racemic zopiclone have been reported in European postmarketing reports, most often associated with overdose with other CNS-depressant agent. Signs and symptoms of overdose effects of CNS depressants can be expected to present as exaggerations of the pharmacological effects noted in preclinical testing.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01198

HMDB ID

HMDB0015329

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Thomas Jerussi, “Compositions comprising zopiclone derivatives and methods of making and using the same.” U.S. Patent US20040147521, issued July 29, 2004.

MSDS

Not Available

General References

1. Liu HJ, Sato K, Shih HC, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of the central action of zopiclone: effects on locomotor activity and brain monoamines in rats. Int J Clin Pharmacol Ther Toxicol. 1985 Mar;23(3):121-8.

2. Sato K, Hong YL, Yang MS, Shibuya T, Kawamoto H, Kitagawa H: Pharmacologic studies of central actions of zopiclone: influence on brain monoamines in rats under stressful condition. Int J Clin Pharmacol Ther Toxicol. 1985 Apr;23(4):204-10.

3. Julou L, Bardone MC, Blanchard JC, Garret C, Stutzmann JM: Pharmacological studies on zopiclone. Pharmacology. 1983;27 Suppl 2:46-58.

4. Blanchard JC, Julou L: Suriclone: a new cyclopyrrolone derivative recognizing receptors labeled by benzodiazepines in rat hippocampus and cerebellum. J Neurochem. 1983 Mar;40(3):601-7.

5. Dundar Y, Dodd S, Strobl J, Boland A, Dickson R, Walley T: Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis. Hum Psychopharmacol. 2004 Jul;19(5):305-22.

Zopiclone (CHEM002373)

Structure for CHEM002373: Zopiclone