Zopiclone (Imovane, Zimovane, Ximovan, Rhovane) is a short-acting non-benzodiazepine
prescribed for insomnia. It is rapidly absorbed and has sedative, anti-anxiety, anticonvulsant and muscle relaxing effects.
[top]Introduction to Zopiclone
Zopiclone was introduced in 1986 as a safer alternative to benzodiazepine drugs
, as it was believed to have less potential than benzodiazepines for developing tolerance, dependance and abuse. Zopiclone has pharmacological effects very similar to benzodiazepines. It is sedating, anxiety reducing, anticonvulsant and muscle relaxing. Zopiclone increases the action of GABA because it is a type A gamma-aminobutyric acid (GABA) receptor agonist. Zopiclone improves sleep continuity by increasing total sleep time, reducing the time it takes to fall asleep, and reducing the number of awakenings in both insomniacs and healthy individuals. Many, but not all, studies have found zopiclone increases slow wave sleep; some report zopiclone causes a reduction of REM sleep similar to that of benzodiazepines.
Zopiclone is prescribed in oral formulation, in 5.0 mg and 7.5 mg doses.
Eszopiclone (Lunesta), the active stereoisomer of zopiclone, is prescribed in oral formulation in 1 mg, 2 mg, and 3mg doses.
[top]Ways of Administration
[top]Oral administration of Zopiclone
Zopiclone has oral bioavailability >75%, so oral administration is standard and effective. The standard therapeutic dose of zopiclone is 3.75-15 mg, taken shortly before bed for insomnia.
) is not a recommended route of administration because zopiclone is not water soluable, and so will not be absorbed by the mucous membranes. Any sedative effect from snorting zopiclone will result from it dripping down to the stomach and being absorbed.
[top]Effects of Zopiclone
As a sedative/hypnotic zopiclone reduces central nervous system activity and causes relaxation and drowsiness. Taken as prescribed, zopiclone will reduce sleep latency (the time it takes to fall asleep), increase total sleep time, and reduce REM sleep. A bad metalic taste and amnesia are commonly reported side-effects of zopiclone use.
[top]Combinations with Zopiclone
Central nervous system depressants
and benzodiazepines have an additive effect if taken with zopiclone, significantly increasing the risk of adverse sedative effects. Opiate
drugs can also have an additive effect when combined with zopiclone, raising the risk of adverse effects such as respiratory depression.
Zopiclone is known to interact with a number of medications. Medications which increase
zopiclone's effects are erythromycin (antibiotic), itraconazole (antifungal), sulfaphenazole (antibacterial).
Medications which decrease
zopiclone's effects are rifampicin (antibiotic), ketoconazole (antifungal), phenytoin (anticonvulsant) and carbamazepine (anticonvulsant).
[top]Different Uses for Zopiclone
[top]Pharmacology of Zopiclone
Zopiclone is hypnotic, anti-anxiety, anticonvulsant, and muscle relaxing in its effects. Both slow wave and Stage 2 sleep are increased by zopiclone. Although it is not a benzodiazapine, zopiclone acts in a pharmacologically similar way, enhancing GABA through binding at the benzodiazepine
binding site on α1, α2, α3 and α5 GABAA containing receptors. Both zopiclone and its active metabolite desmethylzopiclone also inhibit NMDA and nAChRs receptors. It has been theorized that zopiclone's inhibition of NMDA and nAChRs receptors is implicated in the addictive properties of zopiclone.
Zopiclone is metabolized in the liver by demethylation, decarboxylation, and side chain oxidation producing metabolites including a weakly active N-oxide derivative and an inactive N-desmethyl metabolite. Approximately half of a dose of zopiclone is converted to other inactive metabolites via decarboxylation. Zopiclone has a half-life
of between 3.5 and 8 hours.
[top]Chemistry of Zopiclone
|Systematic (IUPAC) name:||6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate|
|Synonyms:||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-chloropyridin-2-yl)-5-(4-methylpiperazin-1-yl)carbonyloxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine, RP-27267, Amoban, Imovane, Limovan, Sopivan, Ximovan, Zimovane, (±)-Zopiclone, Rhovane, Zopiclona, Zopiclonum; Eszopiclone, Estorra, Lunesta (S-form)|
|Molar mass:|| 388.81 g/mol|
|CAS Registry Number:||43200-80-2, 138729-47-2 (S-form)|
|Melting Point:||178°C, 206.5°C (S-form)|
|Boiling Point:||no data|
|Flash Point:||no data|
|Solubility:||freely soluble in chloroform and methylene chloride; soluble in dimethylformamide and 0.1 N hydrochloric acid; slightly soluble in acetone; nearly insoluble in water, ethanol, or ethyl ether. (not verified)|
|Notes:||freebase crystallized from acetonitrile/diisopropyl ether 1:1; S-form crystallized from acetonitrile|
[top]The Dangers of Zopiclone
[top]Physical health risks
involves risk of seizure, especially if zopiclone is abruptly stopped or when doses of zopiclone have been increased beyond normal therapeutic amounts.
[top]Next day impairment
A single 7.5 mg dose of zopiclone has been demonstrated to disrupt cognition, memory, and driving and psychomotor performance the morning following bedtime administration.
Severe drowsiness, dyspnea, skin rash.
Deaths due to zopiclone toxicity have been reported but are rare. The fatal toxicity rate for zopiclone is not significantly different from that for benzodiazepines as a group, though lower than alprazolam
) and chlormethiazole. Hypnosedatives like zopiclone are more frequently contributory factors rather than primary substances in poisoning deaths.
[top]Mental health risks
[top]Aggressiveness, loss of inhibitions, confusion, and daytime anxiety
Behaviorial changes associated with use of zopiclone including aggressiveness and extroversion, loss of inhibitions, confusion, daytime anxiety and/or restlessness.
[top]Disturbed thought patterns and amnesia
Zopiclone use is associated with disturbed cognition, including abnormal thoughts, depersonalization, hallucinations, and illusions, and extreme agitation.
[top]Sleep-walking and other complex behaviours
There have been many reports of people engaging in complex behaviors while still asleep from taking zopiclone, include sleepwalking, preparing food and eating and even driving cars.
[top]Physical Addiction of Zopiclone
Zopiclone should not be abruptly stopped, as this can cause withdrawal symptoms similar to those seen in benzodiazapine withdrawal, including anxiety, rebound insomnia, tremors, tachycardia
, and seizures.
[top]Mental Addiction of Zopiclone
Zopiclone presents some risk of dependence, tolerance and abuse, though the level of risk has been found to be significantly lower for zopiclone than that of benzodiazapines prescribed for sleep difficulties.
[top]Legal Status of Zopiclone
Zopiclone is a controlled substance 21 CFR 1308.14
Zopiclone is not a scheduled substance in Canada's Controlled Drugs and Substances Act (March 2012), but is a Schedule F drug
under Canada's Food and Drugs Act, which means zopiclone may only be dispensed to someone with a prescription.
Zopiclone is a prescription only medication (POM) in the UK and may only be despensed with a valid doctors prescription
Zopiclone is a Prescription only drug, not controlled under the 1977 Misuse of drugs act or any subsequent amendments
The United States Drug Enforcement Administration lists zopiclone under Schedule IV, due to evidence that zopiclone has addictive properties similar to benzodiazepines.
Zopiclone is not commercially available in the United States, though oral preparations of zopiclone's active stereoisomer eszopiclone are commercially available (Lunesta).
[top]History of Zopiclone
[top]Popularity of Zopiclone over time
[top]More Zopiclone Sections
[top]The Latest Zopiclone Threads
, fifteenth edition (2013)
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