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Tilidine/Methylphenidate Structure-/Effect relationship

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c0rt3x

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Today I came to fully realizing that Tilidine is most likely not only a opioid-agonist but probably also a dopamine re-uptake inhibitor.

The structures are not only very similar but might also explain why there are such intense differences between 'stimulating opioids' like oxycodone and 'tranquilizing opioides' like morphine.

This is so far only my guess.


Anyway I have say that me as a long-term chronic back pain as well/worse as ADD patient are greatly benefiting of the harmonizing and somewhat calming effects of mixed Tilidine/Naloxone preperations (retarded ) which have the additional advantage that the naloxone is effectively preventing the common opioid obstipation.


Please feel free to comment. :)
 
The classical opioids aren't dopamine reuptake inhibitors. I personally think it has to do with histamine release; histamine is known to be associated with wakefulness or sedation
 
comparing it to methylphenidate doesn't make much sense, but it can obviously be compared to fencamfamine and other 2-phenylcyclohexanamine derivatives. The only reason I can see to compare it to MPH at all is the relative positioning of the ester.

Anyway, if you go forward and consider it as an analogue of fencamfamine, there might be some sort of connection between FCF's apparent [minor] opioid properties.

Tilidine is not much of an opioid though, most of its activity is derived from its metabolism to nortilidine and bisnortilidine (is the latter active or just another metabolite? I'm not sure...). For whatever reason the n-dealkylated derivatives of tilidine are much better analgesics. I would assume they're also better stimulants.

Does anyone know how fencamfamine, norfencamfamine and N-methyl-fencamfamine (or N-ethyl-fencamfamine for symmetry's sake) would be ranked in terms of potency? If it'd follow the amphetamines, I assume it'd go fencamfamine > norfencamfamine > N-methyl-fencamfamine. I wonder where 1-(3-phenylbicyclo[2.2.1]heptan-2-yl)piperidine would fall then and more broadly about 1-(2-phenylcyclohexyl)piperidine derivatives. With N-methylmethylphenidate you have a virtually inactive drug, but with MDPV you have a really potent one. I would bet that these piperidine derivatives of fencamfamine would be more like MDPV than MPH.

If tilidine or nortilidine do have DAT inhibiting effects, they're obviously quite weak. I mean, doses range from 50 to 600mg. For someone who had developed his tolerance to opioids through tilidine administration it'd be of little consequence, as stimulant tolerance builds fast as well, but to take someone who had developed a sufficiently high tolerance to opioids while on some other opioid that didn't inhibit DAT and switched them to an effective dose of tilidine would be very dangerous.

Tilidine is still probably a good place to look if you wanted a stimulant-opioid whose two effects were well matched up, but tilidine is CI in the US, so it's unlikely an analogue will have much chance in the US.

Oh yes, what exactly is this thread about? And how on earth can you compare tilidine and more classical opioids like oxycodone? What tilidine does it does, but it's so structurally irrelevant to oxycodone and morphine how could this comparison mean anything to them???
 
There is a reversed ester of methylphenidate much used in France, I believe. If I remember correctly, some isomers are stimulant, the others sedative - maybe it's opioid stimulation? They use the acetyl ester - the propionyl ester is likely a better bet. Fencamfamine has opioid activity & some analogs more so (like morphine potency).

EDIT - The drug is called Levophacetoperane & the activity is almost exactly the same as methylphenidate. Once again, the propionyl ester could well have mu agonist activity...
 
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why on earth would the propionyl ester have opioid activity? I don't see *any* thing that would justify that. perhaps a stronger stimulant, but not an opioid.
 
Ester functions of opioids always seem to be most active with 3 carbons. Since this thread is on tilidine - an opioid, I was just mentioning that similar compounds may conceivably have opioid activity.

Check prodine, meperidine, fentanyl (well, it's an amide there) and so on. 3 carbons.

Opioids have their place - if your in a lot of pain they can be important. They are, however, not play things.

Why do you say the propinoate would be a better stimulant? 2 carbons is more potent for phenidate & phacetoperane, AFAIK.
 
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