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Benzo Chemical properties

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mgrady3

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I asked this in a benzo thread in BDD but the conversation topic shifted right away so there were no responses so I thought I'd check here to see if anyone could shed some light on the question:

Anyone know the difference between benzo's in terms of their chemical components, specifically concerning having a halogen attached somewhere in the molecule?

Many benzos: Temazepam, Clonazepam, Alprazolam, Oxazepam, Flurazepam, etc have a Chlorine attached, some even have two (Triazolam), and Midazolam has a Chlorine and Fluorine

but for instance, Nitrazepam does not have a Cl

Does the Nitro-group on the phenyl ring act in the same way as an attached halogen? ie a halogen attached to a phenyl ring.

Does the halogen group mediate potency in any way?
 
i know that the "nitro-benzodiazepines" which are nitrazepam and it's derivatives clonazepam(Klonopin) and flunitrazepam(Rohypnol) are esp. potent both by weight and effects making them commonly sought out and abused. they also have long half lives.

another class of benzos(can't remember the term) that includes alprazolam(Xanax), triazolam(Hacion), and midazolam have short half lives and potent hypnotic/sedative effects. this class is also highly abused.

other benzos generally differ in effect on a case by case basis: temazepam ranks among if not the highest in euphoria and strength of intoxicating effects, while oxazepam(related to temazepam) is considered to be one of the least recreational.
 
What is this undecatetraene shit on Wikipedia? I thought IUPAC allowed for the term "benodiazepine" to be used as a root.

A nitro group at the 7 position (traditional numbering) extends the half life because reduction to the aniline is a slow process.

The very long half life of flunitrazepam comes from it being converted to the fluoro analog of clonazepam by CYP3A4. Then the nitro group must still be reduced, so essentially you're getting two high-potency, high-affinity benzos in one. Must be nice being on a roofie regimen: go to sleep all chill, then wake up butter.

Halogens or nitro groups (electron-withdrawers) on a 7 position help the benzo fit into the binding site better (i.e. boost affinity).

The phenyl aids in lipophilicity. Sticking a halogen (almost always fluorine or chlorine) on the phenyl's 2 position further augments the lipophilicity and has a steric effect that keeps the molecule biased towards one of two conformations (this is easier to explain with diagrams). You'll notice that no benzo has a halogen on the phenyl without having a substituent at the 7 position. Thus: steric effect.

temazepam ranks among if not the highest in euphoria and strength of intoxicating effects
Click to expand...

I don't care for Restorils. They do next to nothing for me.
 
comes from it being converted to the fluoro analog of clonazepam by CYP3A4. Then the nitro group must still be reduced, so essentially you're getting two high-potency, high-affinity benzos in one.
Click to expand...

Does not. It can be excreted without being reduced just fine, and is. Only a small percentage of a dose is reduced to 7-amino.

Flunitrazepam has a long half life because it's so lipophilic. The lipophilic nature is also largely responsible for the potency. It enables it to cross the BBB rapidly. a la heroin vs. morphine, to put simply. It's primary metabolites are desmethylflunitrazepam and 3-hydroxyflunitrazepam. 7-aminoflunitrazepam is also produced, but from what I can tell, only a very small percentage of a dose is reduced. Even if it wasn't, it's unlikely that there'd be much effect on half life (more would be converted to desmethyl or 3-hydroxy, thoughJ)
 
Drugs are metabolized to speed their excretion. Even if it weren't metabolized at all, it'd still be excreted, though I imagine much more slowly. The process turns the lipophilic drug into a much less lipophilic drug so it can be excreted through urine more easily.
 
thanks for the info folks
I'ma physics grad student, doing my best to study a bit of chem/neurochem on the side so as to have a better understanding of what all these drugs I'm taking are actually doing
cheers.
 
triazolam & alprazolam = triazolobenzodiazepines
midazolam = imidazolobenzodiazepine

Triazole has 3 nitrogens, imidazole has 2.


... I guess you could just call them *azolobenzodiazepines, but then I'm not sure how do you pronounce the asterisk...
 
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