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Scopolamine and Cocaine

ClantSauce

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Dec 16, 2016
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Did anyone know that:

Scopolamine and Cocaine have the exact same chemical formula, which is C17H21NO4, but they are different compounds due to a different structure?

I am new to chemistry, so this is probably known by a lot of people that the formula itself doesn't necessarily determine the chemical but I found it interesting.
 
It's not that terribly unusual when you realize the sheer number of possible compounds you can actually make with 17 carbon atoms and change. It's certainly a number you'd need scientific notation to write out. And curiously enough, Wikipedia has 2 more drugs that have that same formula. There's actually a strong opioid called hydromorphinol (or oxymorphol - generated from the reduction of the ketone on oxymorphone), that has the same formula, as well as some B2-adrenergic bronchodialator compound called fenoterol.

Scopolamine and cocaine are closer in structure than you'd think though. They have all the same "bits" roughly, but have them arranged in different places. Both have a phenyl ring, an ester group, a tropane ring, etc. - goes to show that even a small change in structure can produce wildly different effects. Or for an even more simple demonstration, the mirror image of DXO, the active dissociative compound that is generated in your liver when taking DXM, is a compound known as levorphanol, and is actually a very powerful opioid painkiller. Both molecules have the same formula, and technically have the same structure from one point of view. However, the two drugs are like your left and right hand - mirror images of each other that cannot be overlaid exactly even if you rotate them.

One thing to note in chemistry is that the empirical formulas are not very good for describing drug structures. For that, people tend to use the line-drawing "skeletal" formulas, due to their high information density and easy readability, instead of exclusively text based abbreviations or anything else. Empirical formulaeI] are [/I]useful for figuring out the molecular weight quickly though. But in the end, the arrangement of atoms in space plays a much greater role than just what atoms you have exclusively.
 
Thanks man! That's really great information.


I wonder what that opiod hydromorphinol would be like together with cocaine?


Are there any reactions possible where the molecules can rearrange themselves to the other forms without gaining or losing other atoms? (hypothetially speaking) Like if exposed to light or sound waves or something like that?


I've always thought it was fascinating how cocaethylene is formed in vivo by the presence of both cocaine and ethanol and how it has it's own unique effects. I wonder if there's anything you can consume that would turn into cocaine? (I guess even if so it wouldn't stay in that form very long anyway).


About DXM: A couple times when I was 15 I drank an entire family sized bottle of Robitussin DM. I went through a very itchy phase kind of like a niacin flush and then saw a bunch of lightning bolts in my visual field. This was followed by a very droopy feeling (I felt like a bean bag) and a prolonged trance state which lasted all night. I couldn't walk the next morning for several hours!
 
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