Destramadol /(O-desemthyl-desoxytramadol)

[Dr.Heckyll]

Gruenenthal hs recentry patented Destramadol. It's an opioid and SSRI. It's supposed to have opioid, SSRI and anyiolytic properties in a well balanced manner. Sounds good, doesn't it?

Now that's only one enantiomer. The other has much stronger opioid effects. So the recamate should be just perfect.

Patent number for the curious is WO2004009067A1

 

[Survival0200]

It's Grünenthal by the way.

Does that 2004 after WO indicate the year when the patent was approved?

I wonder if it's going to be commercialized, even tho it has a patent now. 8)

Does it differentiate a lot from the metabolite of tramadol; O-desmethyltramadol (w/ out the desoxy part).

P.S. Are you high or something, b/c you're making a lot of typos? :D

 

[Photon]

Sounds like a good SSRI to have, I was on Lexapro for a while and would like the less opiods.

 

[Dr.Heckyll]

Does that 2004 after WO indicate the year when the patent was approved?

No, that's the date the patent was filed.

P.S. Are you high or something, b/c you're making a lot of typos? :D

Yes, too much milk

 

[haribo1]

I've often wondered how difficult it would be to remove that methyl ether. Strong acidic conditions would most likely dehydrate the other alcohol. Maybe strongly basic conditions would do it? The patent cites 46% HBr & 5M NaOH without yields. but then they seem to be dealing with tramadol without that tertiary alcohol which I seem to remember reading was important for activity. IF tramadol could be easily deetherified, then you might end up with something packing a useful punch...

 

[Smyth]

I know someone who made a sample amiunt of desmethyl-tramadol using DIBAH and said he was not sufficiently impressed with this compound fpor it to be worthwhile. If anything he actually preferred the slightly lamer tramadol that has somewhat more predictable effects.

 

[haribo1]

Interesting, so losing that quaternary alcohol might do the thing some good. If I remember, acetylation of the quaternary alcohol destroyed activity, but if that alcohol is gone, acetylation of the phenolic -OH might be very interesting...
Here's a link to the patent:

patent

 

[vecktor]

I've often wondered how difficult it would be to remove that methyl ether. Strong acidic conditions would most likely dehydrate the other alcohol. Maybe strongly basic conditions would do it? The patent cites 46% HBr & 5M NaOH without yields. but then they seem to be dealing with tramadol without that tertiary alcohol which I seem to remember reading was important for activity. IF tramadol could be easily deetherified, then you might end up with something packing a useful punch...

niobium pentachloride, or similar lewis acid.

 

[rashandreflex]

to reitirate survival, are you referring to desmethyltramadol or is O-desemthyl-desoxytramadol different?

 

[Smyth]

That's an interesting patent, one I havent noticed hitherto. Im not a German scholar but im guessing that the key point is that if you remove the tertiary hydroxy and replace this with a hydrogen (in a theoretical sense), doing this does not obliterate potency as might be expected. Although the compounds are still weaker relative to tramadol, they still maintain ~60% residual potency. Is this correct?

 

[haribo1]

It would appear so. Like I said, acetylation of the phenol would allow the drug to jump through the BBB rather fast. Since there are 2 isomers (one an opiate, one an SSRI) then seperating the buggers would be interesting. I would be interested to see if the pure opiate one is actually effective at stopping pain and the SSRI one is truly an amazingly fast-acting antidepressant. Esterification of that phenol would allow a user to smoke the stuff (or, if they are daft, shooting it).