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O-desmethyl-tramadol

kyanite

kyanite

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Joined
Oct 15, 2005
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The drug I'm describing here is Tramadol without the methyl on the phenolic group(-OH instead of -OCH3). A lot of people on Bluelight have tried Tramadol, I haven't, but from what I've read it feels as if it's missing something. Not to mention Tramadol also acts on other systems than the opiate receptors(GABA, adrenergic, serotonin).

Theres a file on the net showing the results of a drug dependance study by Virginia Commonwealth University, and one of the drugs was this O-desmethyl-tramadol(called NIH 10913). It suppresses morphine withdrawals with a morphine like potency in monkeys. Pretty good for a pretty simple compound.
But the question is if Tramadol and this O-desmethyl have a similar relationship like Codeine and Morphine. Roughly 10% of codeine is turned into morphine, O-desmethyl is roughly morphine's potency, and Tramadol is 10% potency morphine given IV/IM. Maybe the opiate effects of tramadol is actually from the O-desmethyl.

Is there any other information on o-desmethyl tramadol? If it doesn't have the adrenergic and serotonin effects of tramadol, then tramadol might be more useful than we think.:\

edit: from wikipedia
Metabolism

Tramadol undergoes hepatic metabolism via the cytochrome P450 isozyme CYP2D6, being O- and N-demethylated to 5 different metabolites. Of these, M1 is the most significant since it has 200 times the μ-affinity of (+)-tramadol, and furthermore has an elimination half-life of 9 hours compared to 6 hours for tramadol itself. In the 6% of the population who have slow CYP2D6 activity, there is therefore a slightly reduced analgesic effect. Phase II hepatic metabolism renders the metabolites water-soluble and they are renally excreted. Thus reduced doses may be used in renal and hepatic impairment.

Okay, M1 is the o-desmethyl-tramadol, so apparently it's pretty potent... any more info?
 
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you're right. o-desmethyltramadol is the active opioid. tramadol is just a snri. but that's no overwhelming new information.
btw: it's not that easy to demethylate tramadol as it might seem. it's due to the tertiary hydroxyl which would get removed in such an attempt.
 
Hehe, yeah I see that now. All that's left to wonder is if O-desmethyl tramadol's good by it self... That hydroxy group, you think it would do any good being a methyl? I don't see a purpose for it except for keeping the cyclohexane ring in position. Probably would help it's pharmcodynamics too.
 
morphiquet said:
you're right. o-desmethyltramadol is the active opioid. tramadol is just a snri. but that's no overwhelming new information.
btw: it's not that easy to demethylate tramadol as it might seem. it's due to the tertiary hydroxyl which would get removed in such an attempt.
Click to expand...

Spot on. desmethyltramadol binds to the mu receptor 100x more that tramadol but if you tried to remove that ether, the quat -OH dehydrates. I wondered about esterification. Reflux tramadol in GAA, then bubble in some HBr & reflux again. Careful de-esterification would yield the product. Oh, and acetyl tramadol isn't active at all. Oh, but the dehydrated tramadol was still active so you COULD just do a simple demethylation, accept the dehydration and end up with a still very active (about 60% of desmethyl).
 
Has ANYONE ever tried desmethyl? Maybe a report will pop up somewhere of a chemist trying it or something, maybe it will even turn up on the RC market.

Must say wouldn't like to be the guinea pig on this one, tramadol can be quite strange at times.
 
I've tried desmethyl tramadol from Sigma-Aldrich. It's more or less half way between morphine & codeine. Snorted it kicks in at about 3 minutes. Very euphoric and long-lasting. It caused me some hyperthermia but that was the only side-effect off 100mg of the HCl salt.
 
^ How is it sold? It's not a patented drug, right? Was it just sold as a (research) "chemical?" Licensing, etc...
I love tramadol, hence my curiosity.
 
This is going back a decade! 1g was about $200. Yes it was freebase but that's hardly difficult to sort out.
 
No it doesn't MTPP is a VERY specific drug. If you change the N-methyl it becomes non-toxic. In tramadol. the methyl is in a totally different place. It was tested a lot and showed no more toxicity (or only slightly more) than tramadol.
 
well there are enough RC sources selling this for arround 40€ per g, Sigma is just selling this as a analytical standard for drug labs as a reference.

I have never used any other opiates (despite some kratom) but I like it very much 50mg oraly are very relaxing :) at 70mg I start noding a bit, but people with opiate experience need over 200mg for a good turn so its still not very cheap (for them atleast for me its perfect).
 
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