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Ethyl Ester Analogues of DARIs?

Ham-milton

Ham-milton

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I was doing a little research about how ethyl cocaine is formed and I came across Ethylphenidate, which is formed in the body when methylphenidate and alcohol are taken, just like ethyl cocaine.

Since the ethyl ester is more dopamine selective than the methyl in both cocaine and methylphenidate, the methyl probably isn't worth bothering with (or maybe it is, maybe the messiness would turn out to be good) if you were synthing it.

Does anyone know if any of these have been tested? I was thinking of MDPV, but that's already dangerously potent, but there are all sorts of others that could be tried.

Any ideas on how it would affect the activity of psychedelic PEAs?

Hammilton
 
I didn't think MDPV had an ester. it wouldn't be hard to do at all...and I just caught myself before stepping dangerously close to the no synth discussion line.
 
as a general rule the ethyl esters of the various phenidates and the tropanes, and also the isopropyl esters and beyond have higher potencies, longer duration and slower onset, though they tend to have more Area Under the Curve when it comes to extracellular dopamine so are more potent/ effective they are not necessarily what you want for recreational potential. There are a few exceptions to the rule where the ester is highly lipophillic.
 
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I'm going on the assumption that you stumbled accross my post which I mentioned in the cocaethylene thread.

Yes, if you want a copy of the original paper, as usual for these types of queries, PM me with your email and I dont mind running a favor so that you get an opportunity to read it. I'm currently busy writing up contracts for the commercial property im renting, but I still have a few spare minutes leftover to cram into my executive calender.

Methylesters are the most potent, but also the most easily hydrolyzed, so they have a shorter duration of action.

The key consideration is that enantioselectivity becomes more important as the R group increases in size. For methylphenidate it is common to serve up the racemic product. Focalin is the R,R isomer of methylphenidate. As you increase the size of the ester, the S,S isomer of 'alkyl'-phenidate becomes completely inactive.
 
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wouldn't you think......

that the reverse esters would get clipped by esterases pretty quickly and your compounds would be adrenergics?
 
You said in the cocaethylene thread:

You would have to selectively remove the methyl ester with out cleaving the benzoyl ester to produce pure benzoylecognine, which then has to be re-esterified with ethanol, without scrambling of the benzoyl ester to any great degree. This is a problem to do by using chemical reagebts, but is relatively easier by selective methyl esterase enzymes in the bloodstream.
Click to expand...

Are there enzymes that can cleave esters where the alcohol is much bigger than methyl/ethyl? If so the benzoate of cocaine should be cleaved pretty quickly. If not Rem. B's reverse esters should be pretty stable as they are esters of fairly huge alcohols.
 
So wait, the methyl ester is more potent, but the ethyl is more dopamine selective?
 
On a similar topic does anyone know of any information on MDPV (or it's originally licensed cousins) metabolites?

In particular are hydroxy (in replacement of the beta ketone) metaolites produced?

If so anyone speculate on if they would account for peripherally (like ephedrine) side effects?
 
The reverse ester of methylphenidate, Phacetoperane, has the problem that one enantiomer is a sedative, while the other is a stimulant. So you have to separate the enantiomers to get a useful product. Levophacetoperane was marketed in France as a weight loss drug under the name Lideparan. It's more potent than methylphenidate.
 
Wow, well, is seperation such a bitch? You could sell one isomer as a stimulant and the other as a sedative, therefore nothing is wasted...
 
(just guessing) would the sedative isomer more be in the realms of dopamine antagonists (I.e anti-psychotics)?
 
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