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Depressant · Hallucinogen

Zopiclone

Also called Zimovane, Imovane, Amoban, Ximovan, Limovan

Original Wikipedia articleen.wikipedia.org/wiki/Zopiclone revision used (24 October 2026)

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Part of the metabolic pathway of Zopiclone. See the timeline on the metabolic highway.

Enzymes that break it down: CYP3A4 and CYP2E1. Wikipedia’s drug infobox says: “Hepatic through CYP3A4 and CYP2E1” (revision 1369948564).

Common dose · Oral15–15 mg PW
Onset10–30 minutes PW
Total3.5–9 hours PW

Dosage

When sources disagree, both rows are shown as published. Nothing is averaged or merged.

Oral

SourceThresholdLightCommonStrongHeavy
PsychonautWiki2 mg PW3.5–5 mg PW15–15 mg PW30–30 mg PW60 mg+ PW⚠ The source's own markup is broken here, so this is how a reader of the source would see it.
TripSit3.5 mg TS3.5–5 mg TS5–7.5 mg TS7.5–15 mg TS15–22.5 mg TS

Bioavailability: 52–59% PW⚠ PsychonautWiki itself has flagged this text: citation needed.

TripSit dose text

TripSit's factsheet also states its doses as text.

Oral Threshold: 3.5mg Light: 3.5-5mg Common: 5-7.5mg Strong: 7.5-15mg Heavy: 15-22.5mg TS

What dose are you on? (self-reported, unverified)
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Duration

Route · sourceOnsetCome-upPeakOffsetTotalAfter-effects
Oral · PsychonautWiki10–30 minutes PW–3–4 hours PW–3.5–9 hours PW–

TripSit factsheet

Onset
15 minutes TS
Duration
3.5-9 hours TS
Aftereffects
1-12 hours TS

Mixing

For best safety practice, don't mix this drug with other depressants.

Why: respiratory depression. PsychonautWiki says:

Quotes from PsychonautWiki, CC BY-SA 4.0.

Acute combinations: what happens when these are taken close together. Entries backed by a medical journal or agency are listed first.

Backed by medical journals

Awaiting sourcePeer-reviewed reports on acute combinations, from PubMed and the journals the harm reduction sites cite.

Other documented combinations

  • Depressants (1,4-Butanediol, 2-methyl-2-butanol, alcohol, barbiturates, GHB/GBL, methaqualone, opioids) - This combination can result in dangerous or even fatal levels of respiratory depression. These substances potentiate the muscle relaxation, sedation and amnesia caused by one another and can lead to unexpected loss of consciousness at high doses. There is also an increased risk of vomiting during unconsciousness and death from the resulting suffocation. If this occurs, users should attempt to fall asleep in the recovery position or have a friend move them into it. PW⚠ PsychonautWiki lists this combination without a danger rating.
  • Dissociatives - This combination can result in an increased risk of vomiting during unconsciousness and death from the resulting suffocation. If this occurs, users should attempt to fall asleep in the recovery position or have a friend move them into it. PW⚠ PsychonautWiki lists this combination without a danger rating.
  • Grapefruit - Caution should be taken when zopiclone is taken with grapefruit as it inhibits CYP3A4 prolonging zopiclone's duration and potentiates its sedative effect. PW⚠ PsychonautWiki lists this combination without a danger rating.

Risks and toxicity

Zopiclone is generally thought to have a low toxicity relative to dose. However, it is potentially lethal when mixed with depressants like benzodiazepines, alcohol or opioids. When combined with one or several of these substances the already existing chance of a having a "black-out" is significantly increased, leaving the user with very little to no memory of the events that occurred whilst under the influence of zopiclone alone or combined with most other CNS depressants. PW

Some users have reported taking zopiclone in combination with alcohol in an attempt to treat hangovers with varying degrees of success. PW

It is strongly recommended that one use harm reduction practices when using this substance. PW

Dependence and abuse potential

Zopiclone is extremely physically and psychologically addictive. This compound may have an even greater addictive potential than benzodiazepines. Tolerance will develop to the sedative-hypnotic effects within a couple of weeks of daily use. After cessation, the tolerance returns to baseline in 7 - 14 days. Withdrawal symptoms or rebound symptoms may occur after ceasing usage abruptly following a few weeks or longer of steady dosing, and may necessitate a gradual dose reduction. PW

Zopiclone presents cross-tolerance with all benzodiazepines, meaning that after its consumption benzodiazepines and most other GABAgenic depressants will have a reduced effect.[12] PW

TripSit factsheet

Contraindications
Liver disease, myasthenia gravis, severe chronic bronchitis, emphysema, sleep apnea, thyroid gland abnormalities, trimipramine, caffeine, alcohol, erythromycin, itraconazole, rifampicin, phenytoin, carbamazepine, ketoconazole, sulfaphenazole, and nefazodone[1] TS

Testing

Awaiting sourceReagent reactions and test kit guidance from a harm reduction testing service.

Effects

Lethargytirednessa dreamlike state while awakecan induce heavy sleep TS

Overview

Zopiclone (also known by the trade names Zimovane and Imovane) is a non-benzodiazepine hypnotic substance of the cyclopyrrolone class. It belongs to a family of substances colloquially known as "Z-drugs", which includes zaleplon (Sonata) and zolpidem (Ambien and AmbienCR). The mechanism of action is benzodiazepine-like GABA binding activity. PW

A nonbenzodiazepine sedative sleep aid (Z-drug), which can have hallucinogenic effects if taken while awake. Often causes users to have a metallic taste in the mouth for ~12h. Has been reported in some cases to cause certain users to black out, redose excessively and undertake dangerous activities such as driving.[1] TS

Zopiclone, sold under the brand name Imovane among others, is a benzodiazepine-like drug (Z-drug) used as a pharmaceutical treatment for insomnia. While molecularly distinct from benzodiazepine drugs, zopiclone's mechanism of action is similar: it increases the transmission of the neurotransmitter gamma-aminobutyric acid (GABA) in the central nervous system, via positive allosteric modulation at GABAA neurons. Zopiclone is considered a sedative and CNS depressant. Zopiclone and other benzodiazepine-like drugs like zaleplon and zolpidem are addictive. Within days to weeks, the body can become accustomed to the effects of zopiclone. The risk of developing tolerance with benzodiazepine-like drugs is comparable to benzodiazepines. When the dose is then reduced or the drug is abruptly stopped, withdrawal symptoms similar to those of benzodiazepine withdrawal may result.[2][3][4] WP

Benzodiazepine-like drugs decrease sleep latency by 10 to 20 minutes. However, no benzodiazepine-like drug has shown clinically significant increase in total sleep time. Zopiclone is recommended only to be taken at the lowest effective dose, with a duration of 2–3 weeks, for short-term insomnia. Use of zopiclone more than 4 weeks is not recommended. It is dangerous to take with benzodiazepines, sedatives, alcohol or other drugs affecting the central nervous system.[3][5–9] WP

In the United States, zopiclone is not commercially available, although its active stereoisomer, eszopiclone, is. Zopiclone is a controlled substance in the United States, Japan, Brazil, New Zealand and some European countries, and may be illegal to possess without a prescription.[10][11] WP⚠ Wikipedia itself has flagged this text: citation needed.

History

History

Zopiclone was developed and first introduced in 1986 by Rhône-Poulenc S.A., now part of Sanofi, the main worldwide manufacturer. Initially, it was promoted as an improvement on benzodiazepines, which has since been disproven. On April 4, 2005, the U.S. Drug Enforcement Administration listed zopiclone under schedule IV, due to evidence that the drug has addictive properties similar to benzodiazepines.[13] WP

Zopiclone, as traditionally sold worldwide, is a racemic mixture of two stereoisomers, only one of which is active. In 2005, the pharmaceutical company Sepracor of Marlborough, Massachusetts, began marketing the active stereoisomer eszopiclone under the name Lunesta in the United States. This had the consequence of placing what is a generic drug in most of the world under patent control in the United States. Generic forms of Lunesta have since become available in the United States. Zopiclone is currently available off-patent in a number of European countries, Brazil, Canada, Hong Kong, and New Zealand. The eszopiclone/zopiclone difference is in the dosage—the strongest eszopiclone dosage contains 3 mg of the therapeutic stereoisomer, whereas the highest zopiclone dosage (10 mg) contains 5 mg of the active stereoisomer.[14][15] WP⚠ Wikipedia itself has flagged this text: citation needed.

Pharmacology

Pharmacology

The therapeutic pharmacological properties of zopiclone include hypnotic, anxiolytic, anticonvulsant, and myorelaxant properties. Zopiclone and benzodiazepines bind to the same sites on GABAA receptors, causing an enhancement of the actions of GABA to produce the therapeutic and adverse effects of zopiclone. The metabolite of zopiclone desmethylzopiclone is also pharmacologically active, although it has predominately anxiolytic properties. One study found some slight selectivity for zopiclone on α1 and α5 subunits, although it is regarded as being unselective in its binding to GABAA receptors containing α1, α2, α3, and α5 subunits. Desmethylzopiclone has been found to have partial agonist properties, unlike the parent drug zopiclone, which is a full agonist. The mechanism of action of zopiclone is similar to benzodiazepines, with similar effects on locomotor activity and on dopamine and serotonin turnover.[18–22] WP

Zopiclone is in the cyclopyrrolone family of drugs. Other cyclopyrrolone drugs include suriclone. Zopiclone, although molecularly different from benzodiazepines, shares an almost identical pharmacological profile as benzodiazepines, including anxiolytic properties. Its mechanism of action is by binding to the benzodiazepine site and acting as a full agonist, which in turn positively modulates benzodiazepine-sensitive GABAA receptors and enhances GABA binding at the GABAA receptors to produce zopiclone's pharmacological properties. In addition to zopiclone's benzodiazepine pharmacological properties, it also has some barbiturate-like properties.[23–27] WP

Pharmacokinetics

After oral administration, zopiclone is rapidly absorbed, with a bioavailability around 75–80%. Time to peak plasma concentration is 1–2 hours. A high-fat meal preceding zopiclone administration does not change absorption (as measured by AUC), but reduces peak plasma levels and delays its occurrence, thus may delay the onset of therapeutic effects. WP

The plasma protein-binding of zopiclone has been reported to be weak, between 45 and 80% (mean 52–59%). It is rapidly and widely distributed to body tissues, including the brain, and is excreted in urine, saliva, and breast milk. Zopiclone is partly extensively metabolized in the liver to form an active N-demethylated derivative (N-desmethylzopiclone) and an inactive zopiclone-N-oxide. Hepatic enzymes playing the most significant role in zopiclone metabolism are CYP3A4 and CYP2E1. In addition, about 50% of the administered dose is decarboxylated and excreted via the lungs. In urine, the N-demethyl and N-oxide metabolites account for 30% of the initial dose. Between 7 and 10% of zopiclone is recovered from the urine, indicating extensive metabolism of the drug before excretion. The terminal elimination half-life of zopiclone ranges from 3.5 to 6.5 hours (5 hours on average).[28] WP

The pharmacokinetics of zopiclone in humans are stereoselective. After oral administration of the racemic mixture, Cₘₐₓ (time to maximum plasma concentration), area under the plasma time-concentration curve (AUC) and terminal elimination half-life values are higher for the dextrorotatory enantiomers, owing to the slower total clearance and smaller volume of distribution (corrected by the bioavailability), compared with the levorotatory enantiomer. In urine, the concentrations of the dextrorotatory enantiomers of the N-demethyl and N-oxide metabolites are higher than those of the respective antipodes. WP

The pharmacokinetics of zopiclone are altered by aging and are influenced by renal and hepatic functions. In severe chronic kidney failure, the area under the curve value for zopiclone was larger and the half-life associated with the elimination rate constant longer, but these changes were not considered to be clinically significant. Sex and race have not been found to interact with pharmacokinetics of zopiclone.[28][29][30] WP

Detection in biological fluids

Zopiclone may be measured in blood, plasma, or urine by chromatographic methods. Plasma concentrations are typically less than 100 μg/L during therapeutic use, but frequently exceed 100 μg/L in automotive vehicle operators arrested for impaired driving ability and may exceed 1000 μg/L in acutely poisoned patients. Post mortem blood concentrations are usually in a range of 400 to 3900 μg/L in victims of fatal acute overdose.[31][32][33] WP

Chemistry

Formula
C17H17ClN6O3 PC
CAS number
43200-80-2 PC
Molar mass (g/mol)
388.8 PC
IUPAC name (computed by PubChem)
[6-(5-chloro-2-pyridinyl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] 4-methylpiperazine-1-carboxylate PC
SMILES
CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl PC
InChIKey
GBBSUAFBMRNDJC-UHFFFAOYSA-N PC
PubChem CID
5735

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Pop culture

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References

  1. Journal / agency Dependence potential of zopiclone studied in monkeys
  2. Journal / agency Victorri-Vigneau C, Gérardin M, Rousselet M, Guerlais M, Grall-Bronnec M, Jolliet P. An update on zolpidem abuse and dependence. Journal of Addictive Diseases. 2014. doi:10.1080/10550887.2014.882725 · PMID 24467433
  3. Journal / agency Riemann D, Espie CA, Altena E, Arnardottir ES, Baglioni C, Bassetti CL, Bastien C, Berzina N, Bjorvatn B, Dikeos D, Dolenc Groselj L, Ellis JG, Garcia-Borreguero D, Geoffroy PA, Gjerstad M, Gonçalves M, Hertenstein E, Hoedlmoser K, Hion T, Holzinger B, Janku K, Jansson-Fröjmark M, Järnefelt H, Jernelöv S, Jennum PJ, Khachatryan S, Krone L, Kyle SD, Lancee J, Leger D, Lupusor A, Marques DR, Nissen C, Palagini L, Paunio T, Perogamvros L, Pevernagie D, Schabus M, Shochat T, Szentkiralyi A, Van Someren E, van Straten A, Wichniak A, Verbraecken J, Spiegelhalder K. The European Insomnia Guideline: An update on the diagnosis and treatment of insomnia 2023. Journal of Sleep Research. December 2023. doi:10.1111/jsr.14035 · PMID 38016484
  4. Other Långtidsbehandling med Imovane. 2018
  5. Journal / agency Sateia MJ, Buysse DJ, Krystal AD, Neubauer DN, Heald JL. Clinical Practice Guideline for the Pharmacologic Treatment of Chronic Insomnia in Adults: An American Academy of Sleep Medicine Clinical Practice Guideline. Journal of clinical sleep medicine: JCSM: official publication of the American Academy of Sleep Medicine. February 2017. doi:10.5664/jcsm.6470 · PMID 27998379 · PMC5263087
  6. Journal / agency Edinoff AN, Wu N, Ghaffar YT, Prejean R, Gremillion R, Cogburn M, Chami AA, Kaye AM, Kaye AD. Zolpidem: Efficacy and Side Effects for Insomnia. Health Psychology Research. 2021. doi:10.52965/001c.24927 · PMID 34746488 · PMC8567759
  7. Other Clinical need and practice - Guidance on the use of zaleplon, zolpidem and zopiclone for the short-term management of insomnia. 28 April 2004
  8. Journal / agency Van Der Kleijn E. Effects of zopiclone and temazepam on sleep, behaviour and mood during the day. European Journal of Clinical Pharmacology. 1989. doi:10.1007/BF00558155 · PMID 2744064
  9. Journal / agency Kuitunen T, Mattila MJ, Seppala T. Actions and interactions of hypnotics on human performance: single doses of zopiclone, triazolam and alcohol. International Clinical Psychopharmacology. April 1990. PMID 2201724
  10. Other Zopiclone consumer information from
  11. Journal / agency Administration DE, Justice DO. Schedules of controlled substances: placement of Zopiclone into schedule IV. Final rule. Federal Register. April 2005. PMID 15806735
  12. Other Zopiclone and triazolam in insomnia associated with generalized anxiety disorder. If zopiclone has been taken for more than a few weeks, then the medication should be gradually reduced or preferably crossed over to an equivalent dose of diazepam (Valium) which has a much longer half-life, making withdrawal easier. One should then gradually taper the dose over a period of several months to avoid extremely severe and unpleasant withdrawal symptoms which can last up to two years after withdrawal if the withdrawal is done too abruptly
  13. Journal / agency Holbrook AM, Crowther R, Lotter A, Cheng C, King D. Meta-analysis of benzodiazepine use in the treatment of insomnia. CMAJ. January 2000. PMID 10674059 · PMC1232276
  14. Journal / agency Blaschke G, Hempel G, Müller WE. Preparative and analytical separation of the zopiclone enantiomers and determination of their affinity to the benzodiazepine receptor binding site. Chirality. 1993. doi:10.1002/chir.530050605 · PMID 8398600
  15. Journal / agency Fernandez C, Maradeix V, Gimenez F, Thuillier A, Farinotti R. Pharmacokinetics of zopiclone and its enantiomers in Caucasian young healthy volunteers. Drug Metabolism and Disposition. November 1993. doi:10.1016/S0090-9556(25)08209-1 · PMID 7905394
  16. Other https://ccsa.ca/sites/default/files/2019-04/CCSA-Canadian-Drug-Summary-Prescription-Sedatives-2017-en.pdf
  17. Other AMVV - Verordnung über die Verschreibungspflicht von Arzneimitteln
  18. Journal / agency Röschke J, Mann K, Aldenhoff JB, Benkert O. Functional properties of the brain during sleep under subchronic zopiclone administration in man. European Neuropsychopharmacology. March 1994. doi:10.1016/0924-977X(94)90311-5 · PMID 8204993
  19. Journal / agency Petroski RE, Pomeroy JE, Das R, Bowman H, Yang W, Chen AP, Foster AC. Indiplon is a high-affinity positive allosteric modulator with selectivity for alpha1 subunit-containing GABAA receptors. The Journal of Pharmacology and Experimental Therapeutics. April 2006. doi:10.1124/jpet.105.096701 · PMID 16399882
  20. Journal / agency Atack JR. Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site. Current Drug Targets. CNS and Neurological Disorders. August 2003. doi:10.2174/1568007033482841 · PMID 12871032
  21. Journal / agency 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. International Journal of Clinical Pharmacology, Therapy, and Toxicology. March 1985. PMID 2581904
  22. Journal / agency 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. International Journal of Clinical Pharmacology, Therapy, and Toxicology. April 1985. PMID 2860074
  23. Journal / agency Blanchard JC, Julou L. Suriclone: a new cyclopyrrolone derivative recognizing receptors labeled by benzodiazepines in rat hippocampus and cerebellum. Journal of Neurochemistry. March 1983. doi:10.1111/j.1471-4159.1983.tb08023.x · PMID 6298365
  24. Journal / agency Skerritt JH, Johnston GA. Enhancement of GABA binding by benzodiazepines and related anxiolytics. European Journal of Pharmacology. May 1983. doi:10.1016/0014-2999(83)90494-6 · PMID 6135616
  25. Journal / agency De Deyn PP, Macdonald RL. Effects of non-sedative anxiolytic drugs on responses to GABA and on diazepam-induced enhancement of these responses on mouse neurones in cell culture. British Journal of Pharmacology. September 1988. doi:10.1111/j.1476-5381.1988.tb16554.x · PMID 2905900 · PMC1854132
  26. Journal / agency Julou L, Bardone MC, Blanchard JC, Garret C, Stutzmann JM. Pharmacological studies on zopiclone. Pharmacology. 1983. doi:10.1159/000137911 · PMID 6142468
  27. Journal / agency Blanchard JC, Boireau A, Julou L. Brain receptors and zopiclone. Pharmacology. 1983. doi:10.1159/000137912 · PMID 6322210
  28. Journal / agency Assessment of Zopiclone. 2006
  29. Journal / agency Gaillot J, Heusse D, Hougton GW, Marc Aurele J, Dreyfus JF. Pharmacokinetics and metabolism of zopiclone. International Pharmacopsychiatry. 1982. PMID 7188377
  30. Journal / agency Viron B, De Meyer M, Le Liboux A, Frydman A, Maillard F, Mignon F, Gaillot J. Steady state pharmacokinetics of zopiclone during multiple oral dosing (7.5 mg nocte) in patients with severe chronic renal failure. International Clinical Psychopharmacology. April 1990. PMID 2387982
  31. Journal / agency Kratzsch C, Tenberken O, Peters FT, Weber AA, Kraemer T, Maurer HH. Screening, library-assisted identification and validated quantification of 23 benzodiazepines, flumazenil, zaleplone, zolpidem and zopiclone in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization. Journal of Mass Spectrometry. August 2004. doi:10.1002/jms.599 · PMID 15329838
  32. Journal / agency Gustavsen I, Al-Sammurraie M, Mørland J, Bramness JG. Impairment related to blood drug concentrations of zopiclone and zolpidem compared to alcohol in apprehended drivers. Accident Analysis & Prevention. May 2009. doi:10.1016/j.aap.2009.01.011 · PMID 19393793
  33. Other Baselt R. Disposition of Toxic Drugs and Chemicals in Man. 2008

Text and values on this page are quoted from PsychonautWiki (CC BY-SA 4.0), Wikipedia (CC BY-SA 4.0), TripSit factsheets, PubChem (public domain). Each value links to the exact revision it came from.