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Eszopiclone
(S)-6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl-4-methyl-1-piperazinecarboxylate
Lunesta, Eszop
Eszopiclone is a nonbenzodiazepine hypnotic of the cyclopyrrolone class and the active S-stereoisomer of zopiclone.citation needed It belongs to the family of drugs colloquially known as "Z-drugs." First approved by the FDA in 2004 for the treatment of insomnia, it is notable for being one of few hypnotic sedatives approved for long-term use. Eszopiclone enhances GABAergic neurotransmission in a manner similar to yet distinct from benzodiazepines and is considered habit-forming.1
Dosage & Duration
Dosage
Doses are population estimates that vary widely between individuals.
Threshold~0.5 mg
Light0.5-2 mg
Moderate2-3 mg
Strong3-6 mg
Heavy6+ mg
Duration
Onset10-20 minutes
Peak0.5-1.5 hours
Total6-8 hours
Half-life
~6 hours
Subjective Effects
Legacy content. A statistically backed ontology from Mindstate Design Labs is coming soon.
The experience is dominated by rapid-onset sedation that typically leads directly into sleep, with pronounced physical relaxation and reduced anxiety. Users who resist the initial wave of sleepiness and remain awake may encounter hallucinatory effects, including basic closed- and open-eye visuals, alongside an emotionally numbed and disinhibited headspace. Memory of the period after ingestion is often unreliable, and residual impairment of coordination and alertness can persist into the following morning, particularly at higher doses.
Physical
Heavy sedation, muscle relaxation, and loss of motor coordination dominate the physical experience, sometimes accompanied by dizziness, headache, nausea, and dry mouth. Complex sleep behaviors such as sleep-walking have been reported.
Cognitive
The headspace is sedated, emotionally blunted, and disinhibited, with anterograde amnesia commonly leaving partial or absent recall of events after ingestion.
Suppressions
The mental state is defined by suppression: thought, emotion, anxiety, and memory formation are all dampened as sedation takes hold.
Visual
Visual effects are not typical at standard hypnotic doses unless the user remains awake past the onset of sleepiness, at which point basic hallucinatory visuals can appear. Hallucinations become more frequent at doses well above the therapeutic range.
Hallucinatory States
Pharmacology
Pharmacodynamics
Eszopiclone acts as a positive allosteric modulator at GABA-A receptors, binding at the benzodiazepine site with full agonist efficacy.citation needed It shows particular affinity for receptors containing α1, α3, and α5 subunits, with additional modulatory activity at α2-containing receptors. This binding enhances GABA-mediated inhibitory signaling by increasing the frequency of chloride channel opening in the presence of endogenous GABA. Eszopiclone also acts as an agonist at the translocator protein (TSPO).
Pharmacokinetics
Eszopiclone is rapidly absorbed after oral administration, with peak plasma concentrations reached within approximately 0.45 to 1.3 hours.citation needed It is 52–59% bound to plasma proteins1 with a volume of distribution of approximately 90 L. The drug undergoes extensive hepatic metabolism via oxidation and demethylation, primarily mediated by CYP3A4 with additional contributions from CYP2C8 and CYP2E1.citation needed The major metabolites are S-desmethylzopiclone, which retains pharmacological activity, and zopiclone-N-oxide, which shows only weak activity. The elimination half-life is approximately 6 hours in healthy individuals but is prolonged in those with hepatic impairment, in elderly patients, and when co-administered with CYP3A4 inhibitors. Less than 10% of an oral dose is excreted in the urine as the parent compound, with the majority eliminated as metabolites.
Dangerous
Highest riskThese combinations are considered extremely harmful and should always be avoided. Reactions to these drugs taken in combination are highly unpredictable and have a potential to cause death.
Dissociatives
Caution
Use cautionThese combinations are not usually physically harmful, but may produce undesirable effects, such as physical discomfort or overstimulation. Extreme use may cause physical health issues. Synergistic effects may be unpredictable. Care should be taken when choosing to use this combination.
1,2-BenzodiazepineAbacavirAbametapirAbataceptAbiraterone
Tolerance
Tolerance timelines are rules of thumb, not exact schedules, and vary widely between individuals and use patterns.
Full Tolerance
Tolerance to sedative-hypnotic effects can build after roughly several weeks of everyday use. Eszopiclone may carry a stronger addiction liability than benzodiazepines.
Cross Tolerance
Benzodiazepines, GABAergic depressants
Baseline Reset
Tolerance returns to baseline within 7-14 days after cessation of use. However, if the substance has been used for extended periods, a gradual tapering process is recommended to avoid severe withdrawal symptoms that can persist for extended durations.
Harm Potential
Addiction & Dependence
Psychological
ModeratePsychological dependence can develop with regular use. Compulsive redosing has been reported as a notable effect. Abuse potential exists, particularly in individuals with a history of substance use disorders, with studies showing eszopiclone produces effects similar to diazepam at supratherapeutic doses.citation needed Use beyond short-term periods is generally not recommended.
Physical
HighPhysical dependence develops after a few weeks of regular dosing. Withdrawal symptoms or rebound effects occur following abrupt cessation and can persist for extended periods if not properly managed through gradual tapering.citation needed Cross-tolerance exists with benzodiazepines, and transitioning to a longer-acting benzodiazepine for tapering is recommended to avoid severe withdrawal.
Toxicity
Immune System
A meta-analysis found a 44% higher rate of mild infections such as pharyngitis or sinusitis in users of eszopiclone and other hypnotic drugs compared to placebo; this appears to be a class effect of sedative-hypnotics rather than specific to eszopiclone.citation needed
Psychosis Risk
Hallucinations, delusions, and delirium can occur, particularly at doses exceeding recommended amounts or when users resist the urge to sleep.citation needed Visual phenomena including shadow people and auditory hallucinations are reported at higher doses, with effects described as similar to but less pronounced than those of deliriants.
History & Culture
Development and Approval
Eszopiclone represents the isolated S-stereoisomer of zopiclone, a cyclopyrrolone sedative-hypnotic that had been available in Europe since 1989. The development of eszopiclone as a distinct pharmaceutical product was undertaken by Sepracor, who marketed the compound under the brand name Lunesta.…
Legality
International
Eszopiclone is not listed under the 1961 Single Convention on Narcotic Drugs. It is not listed under the 1971 Convention on Psychotropic Substances. It is not listed under the 1988 Convention against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.
By Country
Illegal2
NorwayIllegalEszopiclone (eszopiklon; S-zopiclone) is a narcotic in Norway under the Narcotics Regulations. It was added to the narcotics list on 1 June 2026. Import and export of medicines containing eszopiclone require a separate certificate for each shipment, while prescribed products remain in prescription group B.
United KingdomIllegalEszopiclone is a Class C controlled drug in the United Kingdom because it is the S-isomer of zopiclone, which is listed in Part I of Schedule 4 to the Misuse of Drugs Regulations 2001; that Part also controls every stereoisomeric form of a listed substance. Unauthorised possession is prohibited, while possession for medical, dental or veterinary administration in accordance with a prescriber's directions is authorised by the Regulations. Unauthorised production, supply, importation and exportation of a controlled drug are prohibited under the Misuse of Drugs Act 1971, subject to its regulatory and licensing exceptions.
Prescription5
United StatesPrescription onlyClassified as a Schedule IV controlled substance under the Controlled Substances Act.1 Approved by the FDA on December 15, 2004 for the treatment of insomnia.26 The scheduling reflects recognized abuse potential comparable to benzodiazepines.1 Possession without a valid prescription may result in drug charges.
By state
Across the 50 states, D.C., and the permanent territories, most jurisdictions treat Eszopiclone consistently with federal control; listed entries record independently verified differences in state classification or coverage.
District of ColumbiaNot scheduledD.C. Code § 48-902.10(a)(1)27
The District's Schedule IV depressant list does not include zopiclone or eszopiclone. The listed entry covers a material containing a named substance and that substance's salts and isomers; it does not make the unlisted zopiclone family a District Schedule IV substance. The District therefore does not mirror the federal Schedule IV designation in its own Schedule IV instrument.
MainePrescription onlyMaine's Schedule W, X, and Y provisions in 17-A M.R.S. § 1102 do not include eszopiclone; the statute instead places all prescription drugs not in those schedules in Schedule Z. Maine defines a prescription or legend drug to include a drug that federal law requires to bear the prescription-only legend. The current official DailyMed structured product label for eszopiclone is classified as a HUMAN PRESCRIPTION DRUG LABEL, so eszopiclone falls within Maine Schedule Z rather than being assigned Maine's equivalent of federal Schedule IV.
GermanyPrescription onlyArzneimittelverschreibungsverordnung (AMVV), § 1 and Anlage 18
In Germany, medicinal products containing eszopiclone are prescription-only because Eszopiclon is listed in Anlage 1 to the Arzneimittelverschreibungsverordnung. Section 1 restricts dispensing of medicinal products containing listed substances to cases where a medical, dental, or veterinary prescription is present, subject to the regulation's further provisions.
IrelandPrescription onlyMisuse of Drugs Regulations 2017 (S.I. No. 173 of 2017)9
Eszopiclone, the S stereoisomer of zopiclone, is a controlled drug in Schedule 4 Part 1 of the Misuse of Drugs Regulations 2017. The Regulations prohibit production, supply, importation and exportation except as provided, and permit possession of a Part 1 Schedule 4 drug for medical, dental or veterinary administration under a practitioner's directions. The Regulations came into operation on 4 May 2017.
SingaporePrescription onlyEszopiclone is a prescription-only active ingredient under the Health Products (Therapeutic Products) Regulations 2016. The Second Schedule lists zopiclone among active ingredients in prescription-only medicines and expressly includes stereoisomeric forms wherever possible; eszopiclone is zopiclone's S-stereoisomer. Retail supply is therefore limited to the prescription-only medicine framework under the Health Products Act and its therapeutic-products regulations.
Legal / decriminalized2
South KoreaLegal (regulated)MFDS Drug Safety Korea approved-product record 20200217917
South Korea's Ministry of Food and Drug Safety lists an approved eszopiclone product as a prescription medicine and classifies it as a psychotropic narcotic drug. Eszopiclone is legally regulated within the approved-medicine framework.
References
Source Pages
Citations
- Lunesta- eszopiclone tablet, coated. DailyMed (24 May 2023). https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fd047b2b-05a6-4d99-95cb-955f14bf329f1234
- Florendo L. Joya, Daniel F. Kripke, Richard T. Loving, Arthur Dawson, & Lawrence E. Kline. (August 2009). Meta-analyses of hypnotics and infections: eszopiclone, ramelteon, zaleplon, and zolpidem. Journal of Clinical Sleep Medicine, 5(4), 377–383. https://doi.org/10.5664/jcsm.275521
- Eszopiclone - Drug Usage Statistics. ClinCalc (n.d.). https://clincalc.com/DrugStats/Drugs/Eszopiclone1
- Sepracor signs up GSK to sell insomnia drug Lunivia. PharmaTimes (12 September 2007). https://pharmatimes.com/news/sepracor_signs_up_gsk_to_sell_insomnia_drug_lunivia_990850/1
- Sepracor Pharmaceuticals Ltd withdraws its marketing authorisation application for Lunivia (eszopiclone). European Medicines Agency (15 May 2009). https://www.ema.europa.eu/en/news/sepracor-pharmaceuticals-ltd-withdraws-its-marketing-authorisation-application-lunivia-eszopiclone1
- Lunesta (eszopiclone 3 mg tablet) — Health Canada Drug Product Database, DIN 02453223. Health Canada (n.d.). https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=93976123
- Prescription Drug List. canada.ca (n.d.). https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/prescription-drug-list.html1
- Arzneimittelverschreibungsverordnung (AMVV), § 1 and Anlage 1. gesetze-im-internet.de (n.d.). https://www.gesetze-im-internet.de/amvv/BJNR363210005.html1
- Misuse of Drugs Regulations 2017 (S.I. No. 173 of 2017). irishstatutebook.ie (n.d.). https://www.irishstatutebook.ie/eli/2017/si/173/made/en/print1
- Forskrift om endring i forskrift om narkotika (narkotikaforskriften) (FOR-2026-05-15-892). lovdata.no (n.d.). https://lovdata.no/dokument/LTI/forskrift/2026-05-15-8921
Further Reading
Article Status
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Josie Kins · Updated the article · also 1,4-Butanediol, 1B-LSD, 1cP-AL-LAD and 573 more
Josie Kins · Updated the article · also 1,4-Butanediol, 1B-LSD, 1cP-AL-LAD and 573 more
Josie Kins · Updated the article · also 1,4-Butanediol, 1B-LSD, 1cP-AL-LAD and 573 more
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