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Tapentadol

haribo1

haribo1

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Joined
Nov 29, 2006
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Has anyone got a pointer to the patent? I'm fascinated by this stuff. It's almost a 'how simple can we make an opiate' challange. Are there any other opiates with a SINGLE ring system? Even demerol has 2...
 
Not that I know of. That's pretty interesting, actually- that they're even possible. I doubt they'll manage to get one that's very potent or selective, but this is a good way to get multiple-action drugs.

I am amazed it's possible, the more I think about it.
 
About the only thing I can think of that may enhance it's potency is acetylating the phenol. It should lower the BP enough to allow it to be smoked....
 
From what i've read so far about it, thats its going through the motions like all drugs do, its in Phase 2 i believe at the moment.. Its being used for Molar surgery.

"This study shows quite good efficacy compared to 60 mg of morphine," said Dr. Comfort. "It looks like an interesting compound with a dual mechanism of action with an opioid-like effect. In addition, it has a norepinephrine reuptake inhibition."
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Additionally, total pain relief after 4 hours was higher with onset of action appearing more rapidly for patients in the tapentadol HCI 200-mg group compared with those in the morphine sulfate 60-mg group. The mean level of pain relief obtained with morphine sulfate 60 mg was between that achieved with tapentadol HCl 100 mg and 200 mg, they stated.
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http://www.pslgroup.com/dg/2771fe.htm
 
That stuff is amazing, structurewise at least. What does the patent mean to the obvious future grey market trading?
 
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I think, apart from military stuff, the patent has to be made public. Usually it's buried under some boring name...
 
haribo1 said:
Has anyone got a pointer to the patent? I'm fascinated by this stuff. It's almost a 'how simple can we make an opiate' challange. Are there any other opiates with a SINGLE ring system? Even demerol has 2...
Click to expand...

I think this might be the one? The structural family they are claiming looks like it would include tapentadol anyway, and the authors and dates look about right.

US patent 6248737

http://www.google.com/patents?id=boEIAAAAEBAJ&dq=6248737
 
haribo1 said:
Has anyone got a pointer to the patent? I'm fascinated by this stuff. It's almost a 'how simple can we make an opiate' challange. Are there any other opiates with a SINGLE ring system? Even demerol has 2...
Click to expand...

Maybe you just have to eat enough 3-Hydroxy-N,N-dimethyl-phenylpropylamin...
 
Did you read the scientific stuff about Tapentadol, or the other thread I started a week or two, by any chance, US? I think it was decided that it'll probably prove to be quite enjoyable. A Opio-NARI, only thing better would be an Opio-DARI
 
Wow they only go for N,N dimethyl amine, no other nitrogen substituants.
 
a la dimethylthiambutene


Here's an article from the Green Chemistry Archives: Intermediate in Tramadol Production Chems

Might be interesting if you're looking for info about the synthesis. It doesn't contain any direct info, but it could probably help you figure out a synthesis.

First New Drug in Class in 25 years?

According to Wikipedia, if Tapentadol is approved, it'll be the first new drug of it's class in more than 25 years. What class exactly is this? I assume it's opioids, which I guess would be true. But it has so little in common with existing opioids I wonder if it can really be said to belong to the existing classes of opioids, or if they're just considering any agonist as belonging to that class? But then you'd have to include Tramadol, which, AFAIK, was approved fairly recently.
 
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Good point actually, what more do you want, a single molecule speedball?

The line gets a bit fuzzy with these stripped down mu agonists.
 
It'd be hard to imagine anything more enjoyable than a single substance speedball. The single-ring MORA's so far aren't very selective.

The combo sort of reminds me of lefetamine, though that's a 2-ring structure.
 
anyone have a clue about the stereochemistry?

picture for those interested:
Tapentadol.svg


ah fuggit, dont feel like converting an svg

link: http://upload.wikimedia.org/wikipedia/commons/c/c9/Tapentadol.svg
 
Those 2 side-chains and the stereo-chemistry are obviously to place the nitrogen in the right place for activity. The patent lists a lot of chemicals (to cover all the bases) but no discussion into WHY they went this route is there, obviously. Some serious study of the receptors is needed. Still, I still wonder why only the dimethyl was covered. I ASSUME that they must KNOW that other nitrogen substituants are without activity or, at least, much lower activity...
 
Shame adding F groups requires such nasty stuff, the F analog of tramadol seems potent.
 
ouuu

Phenylephrine, the drug that replaced ephedrine to curb meth production/use may have a use afteral.

With enough work.
 
Bah, forgot it was missing the alpha methyl.

Oh well, its still an idea.
 
Ive been prescribed tapentadol er for a while now, it doesnt seem to have any effect on me, i have quite a high tollerance. as i cant find a way to prep these to shoot i decieded to give plugging a go. i didnt expect but bot was i wrong, 100mg er has given me a very europhic nod (not unlike 50mcg 25mcg fentynal extracted and iv'd completely to my surprise!!! Just thought id throw in my 2 cents (haha even know i should say 2 pennies as im from the uk). I would highly recomend it as the oral biovaibility seems rather low. i used to be a big tramadol lover, but for me the way forward is to plug tapents.
 
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