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  • BDD Moderators: Keif’ Richards

Is methylphenidate at all chemically similar to cocaine?

J

Jimmy_Pop

Bluelighter
Joined
Apr 28, 2012
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Okay, so I was thinking about posting this in advanced drug discussion, but my knowledge of chemistry is really really basic, so I'd only be able to understand "basic" answers (even if the question is one that could easily elicit an "advanced" answer).

The reason I'm curious about methylphenidate and coke, is because I do a lot of stimulants, and I've noticed that these two substances share a lot of similarities, and are both "similarly different" to amphetamines.

Here's what I've noticed.

1. Both provide fairly short lived effects.

2. Both have a very "sharp" comedown compared to amphetamines. With speed, the high lasts really long and tapers off really gradually; with ritalin or coke, it's more like a lightbulb turning off.

3. Both have a somewhat "emotional" comedown. I find coming down off amphetamines really isn't much more than a sketchy, somewhat sickening feeling. Ritalin and coke both have a much more melancholic, brooding, occasionally even "nostalgic" thing going on in the comedown.

4. Both make you want to re-dose again and again and again, and put you in this weird mental fog after you've re-dosed enough times. Never got this with amphetamines.

5. Both apparently metabolize a totally new and more potent drug when taken with alcohol (and both are definitely potentiated by alcohol quite a bit).

Seems like a pretty long list of similarities (though maybe some of these are just me).

Any chemistry pros here able to answer this question?
 
Both are dopamine and norepinephrine reuptake inhibitors, although cocaine is also a serotonin reuptake inhibitor.
 
Methylphenidate belongs to the piperidine class of compounds and increases the levels of dopamine and norepinephrine in the brain through reuptake inhibition of the respective monoamine transporters. Thus, methylphenidate possesses structural and pharmacological similarities to cocaine.

L=Ritalin R=Cocaine
ritalin_cocaine1_shadows.jpg

ritalin_cocaine1_ball_shado.jpg



From the University of Utah:

Like cocaine, Ritalin is a powerful stimulant that increases alertness and productivity. Ritalin and cocaine also look and act the same. Both have a similar chemical structure, and both increase dopamine levels in the brain. They do this by blocking a dopamine transporter protein responsible for the reuptake of dopamine at the synapse.
Click to expand...
 
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Yes, they are fairly closely related actually.

The biggest difference is how quickly each chemical acts. Methylphenidate acts on dopamine and norepinephrine over a 3-6 hour period blocking some of the receptor sites. Cocaine acts over a 30-1 hour long period blocking a much larger amount of receptor sites leading to a very large build up of dopamine that is used during the half hour or so of re-uptake inhibition.

You can see however, if you took the effects of a high dose of methylphenidate that last around 3-6 hours and squished it into a 30 minute period, the effects would be fairly strong.
 
If you build little 3d models of the two molecules, you'll find the active isomer (d-trans-methylphenidate) actually overlays suprisingly well with cocaine!

The piperidine nucleus substitutes for a tropane, nitrogen stays in roughly the same position, the ester link is placed in the same place, phenyl ring in the same "pocket".

The pharmacology of the two compounds is very similar because they are both esters that can be rapidly broken down in the body. And esters can react with alcohgols to from other esters - cocaethylene from cocaine and ethylphenidate from methylphenidate.

Cocaine is acrually *two* esters so it is broken down even faster.
 
They are very, very similar in many ways - the pharmocology has already been stated.

I'd happily take 1g of methylphenidate over the shitty 3% repress coke any day.
I can be going for 18 hours of a quarter gram whereas that qg of coke would last an hour.
 
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