Etizolam (thienodiazepine)

[Ondine]

So etizolam is really making the rounds; from what I've read it seems like a lot of people on here are using it. I was surprised to find out, however, that it isn't technically a benzodiazepine (at least according to wikipedia, which I know isn't always 100% reliable).

Anyway, apparently etizolam differs in structure from benzodiazepines in that it has a thiophene ring in place of a benzene ring. I know that thiophene rings are actually fairly important in pharmacology. My assumption (based partly on reports of etizolam usage), is that the thiophene ring fulfills basically the same role as the benzene ring, but I'm not versed in pharmacokinetics, so I can't be sure. Could there be any significantly different effects brought out by the presence of the thiophene ring, or maybe even more side effects/adverse effects?

 

[Coolwhip]

The sulfur probably results in some weird metabolites(not necessarily active). No idea how it affects the pharmacodynamics.

 

[nuke]

The thiophene ring can generally be used in place of a phenyl ring with usually minor to moderate changes in psychoactivity (sulphur has approximately the same electronegativity as carbon, and the thiophene ring fulfils aromaticity). As was noted, depending on the route of metabolism you may get some unique metabolites.

Like etizolam, olanzapine is a thienobenzodiazepine and has been certified okay for use in schizophrenics (and also contains a gross piperazinyl group, so probably the acute/chronic toxicity isn't a huge concern. But, you never know.

 

[BLreturn11]

I think the definition "benzodiazepine" is getting annoying. [We should be referring to it's activity rather than structure]

Yes etizolam is not a benzodiazepine but like many chemicals it stimulates the "benzodiazepine" receptor. I.e it may not be a benzodiazepine but it could equally be called a 'benzodiazepine receptor agonist'.

Anyway the point, the thiophene is a substantial chemical modification but there are actually quite a few classical 'benzodiazepines' with equally substantial chemical modifications : for example loprazolam.. http://en.wikipedia.org/wiki/Loprazolam .

In other words it would almost be better to refer to compounds as 'benzodiazepine agonists' in a similar way to 'dopamine reuptake inhibitor - I.e it suggests the compound has benzodiazepine agonist properties but it doesn't group together or rule out other pharmacological effects (of which there can be many depending on the compound)