Novel stimulant compounds (perhaps with less spam than the 'stims of the future')

[mad_scientist]

In that patent it lists clofenciclan as another stimulant that is suitable for use with the delivery system they invented.

 

[haribo1]

This may have been mentioned before, not sure what name it would be referred to but what about taking the oxygen out of aminorex/4-MA

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=211124

Yes, that's aminorex.

 

[Reminisant B]

No this is aminorex...

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16630

...it has an oxygen, was wondering what would happen if you replace the oxygen with a carbon (in link above) and still not sure if it has a name or would work.

 

[Reminisant B]

Does anyone know if the Pyrrolidine analogue of methylphenidate was discussed in the stimulants of the future discussion?

 

[<pyridinyl_30>]

^RB,
For some reason, that looks like a very powerful compound to me.

 

[fastandbulbous]

^ Why, if anything going from a 6-membered to a 5 membered heterocyclic ring with such comnpounds results in a drop in potency, sometimes quite dramatic (compare diphenylprolinol with pipradrol)

 

[<pyridinyl_30>]

why not.
2-benzylpiperidine sent me to the hospital once with rhamybylodomysosis (sp).
I'd be afraid to test more than 10mg 2-benzylpyrrolidine initially.

 

[fastandbulbous]

Well most other series if N-heterocyclic stimulants show a drop in activity when going from pipreridine to pyrrolidine based drugs, thats why

 

[<pyridinyl_30>]

ok.

 

[hussness]

^I have been wondering about this observation for a while now. Do you or anyone else have any theories as to why the piperidine moiety often results in higher potency than pyrrolidine? It certainly seems unusual considering, to my knowledge, the piperidine structure is not found in the binding proteins, nor is it in any endogenous ligand.

 

[vecktor]

^I have been wondering about this observation for a while now. Do you or anyone else have any theories as to why the piperidine moiety often results in higher potency than pyrrolidine? It certainly seems unusual considering, to my knowledge, the piperidine structure is not found in the binding proteins, nor is it in any endogenous ligand.

Possibly due to the higher basicity of pyrrolidine versus piperidine.

I think the pyrrolidine nucleus is metabolised more readily than piperdine.

just a few quick ideas..

 

[Reminisant B]

Also wondered what might happen if the beta-ketone on MDPV (or similar compounds) was replaced with the ester moiety from methylphenidate.

(?)

Diagram below

 

[Ham-milton]

I bet the drug is a lot more enjoyable! probably have a shorter halflife, too, no?

 

[<pyridinyl_30>]

^Yes, it should certainly have a shorter half life, if it is active at all that is.

As for the piperidine/pyrrolidine discussion, I don't know the answer but the N-methyl pyrrolidine moiety works great for nicotine (active @ 1mg/70kg body weight).

 

[otb01]

I've always wondered what would happen if they took the ester from methylphenidate and made it a beta ketone and then did substitutions at the 2,4 and 5 positons.

 

[Ham-milton]

Um... I have a stupid question. Are there any analogues of methylphenidate that are opiates?

my internet is being stupid right now (and our lights were flickering earlier) so I'm having trouble getting to the site, but doesn't it look a lot like fentanyl with one fewer nitrogen atom and an oxygen?

 

[fastandbulbous]

If I recall correctly, anabasine is the nicotine analogue with a piperidiner ring & that works OK. Besides, nicotine isn't strictly a central stimulant, that just happens to be an incidental activity to it being an agonist at the nicotinic acetylcholine receptors. Using that as a basis to describe a CNS stimulant opens the flood gate to all sorts of horrible poisonous compounds like strychnine

 

[haribo1]

Also wondered what might happen if the beta-ketone on MDPV (or similar compounds) was replaced with the ester moiety from methylphenidate.

(?)

Diagram below

Now, that IS an interesting idea. The choice of ester could make for more fun as well (methyl, ethyl and so on). Isn't the ethyl analogue of methylphenidate more a pure DAT agonist than the methyl analog?