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The author is not a physician. The content on this website does not, and is not intended to constitute medical advice. It should not be relied upon when making medical decisions. It is not intended as a substitute for advice from your physician or other healthcare provider.

« Seroquel/Quetiapine (Give me a calmative!) | Main | Fluorene (Twist or shine, choose one) »

Eszopiclone/Lunesta (Not quite Valium)

Category: Drugs
Posted on: March 14, 2007 9:00 AM, by Molecule of the Day

Lunesta shares its mechanism of action with the benzodiazepenes - Valium, Rohypnol, Xanax, etc. It doesn't actually belong to the benzodiazepene class of drugs, but they all work on the same system - GABA. Not coincidentally, the much-maligned GHB works by virtue of the fact that it is metabolized to GABA in vivo.

# InChI: InChI=1/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/t16-/m0/s1

Lunesta belongs to a class of drugs that work similarly to benzodiazepenes but in such a way that they have a lower (but still nonzero) potential for abuse and dependency.

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Comments

Some time ago I just put together (with no input form myself) a post with all the information about it in one place. That post is to this day one of the most popular on the old Circadiana blog (though searches, mostly).

Posted by: coturnix | March 14, 2007 11:25 AM

Is it just me or is that something a chemist would not want to put in his mouth? 4-methyl-2-aminopyridine has cardiac adrenergic effects.

Posted by: Uncle Al | March 14, 2007 12:11 PM

So eszopiclone is a pretty damned good sedative/hypnotic, but with very little anxiolytic effect. I believe that's why it has less potential for abuse. BUT, it's metabolite N-desmethyl-(S)-zopiclone actually works at different subunits of the GABAa receptor, making it a pretty effective anxiolytic but not such a great sedative. I think a blind taste test of zop- and desmethylzop- is in order!

Posted by: Brando | March 15, 2007 1:45 PM

I am pretty sure that GHB is not metabolized to GABA, it is mearly an analog

Posted by: Nate | March 15, 2007 10:28 PM

I admit to some ignorance on this, but a quick medline search returns a recent article that at least partially supports the assertion.

I'm glad to be corrected on this (and I can't recall a citation to where I learned this, even a textbook) - anyone, please let me know if you can clear this up.

Posted by: Molecule of the Day | March 15, 2007 11:25 PM

I took a pharma class and I asked if GHB was a GABA agonist, and the professor said that surprisingly, it is not a direct agonist (mimic of GABA). I'm not sure how it works though....

Posted by: Brando | March 16, 2007 3:32 PM

what does it mean if it keeps the patient up longer than before and acts more as a stimulant than a sedative?

Posted by: phataway | June 14, 2007 9:57 AM

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