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O-Desmethoxytramadol

Kronos

Kronos

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Aug 10, 2010
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O-desmethyltramadol analogue apparently, heres the information i have about it:

The analog is a much more interesting molecule that could be called O-Desmethoxytramadol. The only difference between ODM and the analog that we have in stock, is that ODM contains an extra hydroxyl group on the phenol i.e. they're very similar.

2-((Dimethylamino)methyl)-1-phenylcyclohexanol hydrochloride - (IUPAC name)

Structure-activity data suggests that an hydroxyl group reduces a compound's passage through the blood brain barrier. It's therefore likely that the analog would have a more potent neurological effect than ODM. At a guess the analog's potency would be somewhere between ODM and levorphanol.
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I'm no expert on these kind of things, but what are your thoughts? Is this information accurate?
 
He's talking about tramadol with the entire methoxy group removed, not just the methyl group.

I feel pretty certain that removing the methoxy group is a bad idea. The hydroxy group increasing affinity. Might decrease BBB penetrability. Could shield with a readily removed ester. Obviously a trend with opioids, hardly a surprise to anyone.
 
Hammilton said:
He's talking about tramadol with the entire methoxy group removed, not just the methyl group.
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The title of the OP states "O-Desmethoxytramadol", but the post says "O-desmethyltramadol". The first name doesn't even make sense from the chemical point of view.

There is really not much definite information on tramadol's SAR available, but I'd bet that removing the entire methoxy-group would drop potency significantly. This guess is derived from several other opioids with a comparable moiety.


Peace! - Murphy
 
No, the post says 'o-desmethyltramadol analogue'.
The information isnt taken off a vendors page either. Though it is from a vendor, hence why i asked here. Did you even read the post?

Thanks hammilton, guess the only way to find out for sure would be to guinea pig, anyone else knowledgeable have any thoughts/guesses on what it would be like?
 
Did you read my post? The term "O-desmethoxytramadol" doesn't even make sense: "desmethoxy" refers to the removal of a -OCH3-moiety, the "O" refers the the position it was removed from, i.e. the oxygen. Unfortunately is the oxygen already part of the methoxy-group. Read again: It doesn't make sense!
Simply "desmethoxytramadol" would actually make sense, and that's what the provided IUPAC-name says, too. But as I elaborated before:
I'd bet that removing the entire methoxy-group would drop potency significantly. This guess is derived from several other opioids with a comparable moiety.
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But alas! I forgot that you didn't care to read either.
Hammilton actually described the same expected order of potency that I was already referring to:

R-OH > R-OMe > R-H​


ColourfulKronos said:
The information isnt taken off a vendors page either. Though it is from a vendor...
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I get the difference, but this doesn't change the credibility either. In the end, the quality of information is the same. But just for you I re-phrase 4.:

4. Please do not quote vendors. Notoriously unreliable!​

Do you get it now?


ColourfulKronos said:
anyone else knowledgeable have any thoughts/guesses on what it would be like?
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Errrrr ... like weak tramadol maybe?


- Murphy
 
As has already been pointed out O-desmethoxytramadol doesn't exist. The OP probably means o-desmethyltramadol, the M1 CYP2D6 metabolite of tramadol.

You admins and mods are normally to quick to close threads and now this one has been sorted it should probably be closed :)
 
wow still hung up on the simple addition of one letter "O"

simple mistake, was obviously referring to demethoxytramadol. Which as has already been said is a stupid way to go unless you want weaker tramadol with perhaps no opioid receptor affinity at all.
 
The acetate ester of o-desmethyltramadol might be a better way to go.

Some opioids apparently are stronger without the 3-hydroxy group - eg. pethidine - but I doubt tramadol is one of them.
 
Yeah, of course was the nomenclature-issue nothing else than nitpicking, but the OP literally asked for it. :\ I couldn't resist.

And to put this ridiculous discussion to an end:
Tramadol is a ~100-200 weaker µ-agonist in vivo than its O-desmethyl-metabolite ("M1"). On the other hand is the parent compound the more potent reuptake-inhibitor in direct comparison.
How the derivative without any substituent on the phenyl-ring behaves in this respect can only be guessed, as there is no published data available to date, at least none which compares tramadol, M1 and the desmethoxy-derivative in the same publication.

But because the SAR of tramadol follows those of other opioids, which fulfill the classic 'morphine-rule', a significant drop of potency by entirely removing the ortho-O-group is more than likely.


- Murphy
 
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