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Symmetrical Drug Molecules

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Aetherius Rimor

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I came across Cromoglicic acid in my research, an old asthma medication based on Khellin from Ammi Visnaga, and when I looked at the molecular structure, I noticed it was a relatively large (by what I know of so far) molecule with a symmetrical structure:

Wiki: http://en.wikipedia.org/wiki/Cromoglicic_acid
Molecule: http://upload.wikimedia.org/wikiped...licic_acid.svg/800px-Cromoglicic_acid.svg.png

It's quite beautiful to me, so I had to ask, is anyone else aware of other drug molecules that are symmetrical (larger the better)!

Side question, does symmetry in molecular structure give any specific attributes to a compound?
 
Dizocilpine and paraldehyde:

220px-Dizocilpine.svg.png


180px-


These are not very large molecules, though...

Of course if a molecule is symmetrical, its orientation matters less when it approaches a receptor for binding.

EDIT: looking more carefully, dizocilpine doesn't have a plane of symmetry after all, sorry...
 
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Aetherius Rimor said:
is anyone else aware of other drug molecules that are symmetrical
Click to expand...

A handful are mentioned in the comments section of Fearful Symmetry? (In The Pipeline). Here's a big one Suramin.

Aetherius Rimor said:
does symmetry in molecular structure give any specific attributes to a compound?
Click to expand...

In contrast to the potential benefit of lacking specific docking-orientation one user of the above link mentions, "there is more information/mass in a chiral molecule, which would be an advantage in a chiral environment. This is a trend, not a rule. [...] Mother Nature [...] tends to go the chiral route."
 
500px-Sulbutiamine.svg.png


http://en.wikipedia.org/wiki/Sulbutiamine

Not quite symmetrical, but two of the same sub-structure stuck together (I'm sure many of these molecules are not actually symmetrical in 3d space though). It's a thiamine derivative, and a pretty novel stimulant/nootropic. I might take some today now that I think about it, have had some sitting round for ages. Unfortunately if you take it on an empty stomach, you are going to be in hell, not only does it make you puke, but it makes your puke taste so foul it just sends you into a loop of vomiting till your stomachs empty. That's what happened last time I took it, and as a result haven't touched it in a while haha. Taken on a full stomach though, and it's side-effect free, just makes you focused, chatty, motivated, not euphoric in its own right (can make normally euphoric experiences like listening to music better though)

It is by far one of the most bitter substances I've ever come across (toss up between this and pramiracetam). It makes MDMA and meth taste like candy in comparison.

It's method of action is by up-regulating the amount of dopamine receptors, not by releasing excess / inhibiting reuptake of dopamine. So after you've taken it you feel better off than when you started! I've tried it mixed with dextroamphetamine before, its regulation of the dopamine system killed any euphoria I would normally get from d-amp (a lot usually). Perhaps taking it before, then when your dopamine system is upregulated and the drug has stopped working then take d-amp? I must try this one day...
 
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edgar07 said:
It's method of action is by up-regulating the amount of dopamine receptors, not by releasing excess / inhibiting reuptake of dopamine. So after you've taken it you feel better off than when you started! I've tried it mixed with dextroamphetamine before, its regulation of the dopamine system killed any euphoria I would normally get from d-amp (a lot usually). Perhaps taking it before, then when your dopamine system is upregulated and the drug has stopped working then take d-amp? I must try this one day...
Click to expand...

Causing upregulation of receptors!? That's not an effect I've read about yet, interesting.

Also, that molecule does look great... it has rotational symmetry ;)
 
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