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Bromine atoms in my Benzodiapianes

delphinen

delphinen

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First, I am very sorry if this is not the right place to ask this question.
I have been wondering since months what makes the Benzodiapine Bromazepam so enjoyable, more than any others of the same kind; this led me to think about the benzene ring of Bromazepam that has a bromine atom attached to it, so I googled about Bromine everywhere but couldnt find anything about its biochemical properties except that is poisonous in a lot of circumstances.
Finally, getting stuck in my ignorance, I got here asking if you guys could have any idea why and what effects could add the benzene ring with Bromide attached to the a classic Benzodiazepine structure.

Thanks in advance.
 
The position where the bromine is attached, seems to me to be kinda like the 4-position on phenethylamines. The traditional benzodiazepines have a chlorine there. Clonazepam has a nitro. Etc...

All (or most) of the substitutions seem to be halogens or pseudohalogens. So, I think it's just a case of: different halogen, different effects...
 
dread said:
The position where the bromine is attached, seems to me to be kinda like the 4-position on phenethylamines. The traditional benzodiazepines have a chlorine there. Clonazepam has a nitro. Etc...

All (or most) of the substitutions seem to be halogens or pseudohalogens. So, I think it's just a case of: different halogen, different effects...
Click to expand...

Just as I thought, but wasnt sure about it so I didnt post it; so what would be the effects then? I know differente, but why? why the Bromine atom? also.. kinda off topic, why it isnt sold in USA?

Thanks again.
 
When you take 10mg of bromazepam (or whatever a dose is), you only get a small fraction of bromine, say 1mg. I believe therapeutic doses are around 500-1000mg. So what I'm trying to say is I don't think thats enough bromine to do anything. At all. What it does on the structure, I am not entirely sure of, but it can't be that different from the chlorine that is on so many other benzos. Slightly higher, slightly less electronegative... I think its just your imagination.
 
It's not imagination. Bromazepam really does have an almost euphoric effect, especially in one who has no benzo tolerance.

And I don't believe you get any bromine as a metabolite at all. A halogen attached to an aromatic ring usually quite firmly stays there.

Compare the difference between 2C-C and 2C-B... and the difference between diazepam and bromazepam.
 
^ More like nothing.

I don't think there's any evidence that it breaks off of the molecule and leaves you with free bromine in your body. Would be quite bad.
 
It has to do with a term called the heavy atom effect (I > Br > Cl > F).

2ci is more potent than 2cb (on a mg to mg basis; yes, the highs are still qualitatively not the same I know) for the same reason.

Watch out for liver damage with bromazepam though. Hepatotoxicity is not an issue with the other benzodiazepines.
 
"heavy atom effect: The enhancement of the rate of a spin-forbidden process by the presence of an atom of high atomic number, which is either part of, or external to, the excited molecular entity. Mechanistically, it responds to a spin-orbit coupling enhancement produced by a heavy atom.
1996, 68, 2245"
Click to expand...

While it's fun to use big words to sound smart, unless it's correct, it's best done when attempting to impress chicks.

The Heavy-Atom Effect is irrelevant. It's NMR stuff.

1. Adding a halogen won't always result in higher potency

2. Adding a halogen in a different position won't always result in higher potency

It's all about how the drug binds to the receptor. In this case, having a bigger atom there increases potency. That's it.
 
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Go go hammilton.

It would be interesting to know, are there any other correlations between this position in benzodiazepines and the 4-position in phenethylamines...

For example, how would the effect of diazepam change if you would replace the chlorine with an alkyl, alkoxy or alkylthio group...?
 
2c-i is not stronger than 2c-b anyway is it?

i mean if it is then it is marginal and not a strong marked difference in potency.

to the op if u like "bromazepam" then good but i cannot offer a scientific explanation.

its like if somebody says why does lemon juice taste nicer than orange, i mean what kind of answer are u expecting.
 
dread said:
It would be interesting to know, are there any other correlations between this position in benzodiazepines and the 4-position in phenethylamines...
QUOTE]

There's no correlation as it is, so there can't be any other.

They bind to completely unrelated receptors, so what the hell does it matter is two things are similar?

I have two keys in my pocket that are gold colored. They open different locks though, so the color is just chance.
Click to expand...
 
negrogesic said:
Bromine breaking off? 1mg of bromine?

It is simply about binding, not the bromine itself...
Click to expand...
If you're referring to what I said, I was trying to say that it didn't leave the structure, and even if it was free bromine, it would be an insignificant amount. I just typed it rather poorly. The OP was concerned about bromine's toxicity, which is why I wrote that.
 
No it's not remotely a correlation. It's fucking random chance.

All it means is that both receptors have a spot that benefits from a large atom. Big deal.

Chlorine gas is green, so is grass. OH MY GOD! A correlation!
 
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