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O-Desmethyltramadol analog

Part Time Junkie

Bluelighter
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Aug 26, 2010
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UK baby!
Hi just stumbled across this, would be interested to know more about it. Here is all the info I have...

Boiling point 331.56 C (est)
Chemical formula C15H23NO
IUPAC name 2-(dimethylaminomethyl)-1-phenylcyclohexan-1-ol
Melting point 97.43 C (est)
Molecular mass 233.349

Thanks :)
 
The - enantiomer may be a norepinephrine reuptake inhibitor, but i'm pretty sure the meta-hydroxy on the phenyl group is essential for opioid activity.

This compound is O-desmethoxytramadol for those too lazy to find a structure.
 
maybe you should ask fencamfamine?
I doubt you would find out a lot but hey (even though the evidence suggests otherwise) he might actually know something. the use of chemdraw estimate MP's and BP's indicates that the compound hasn't been made, and this is currently a scam. FWIW Same MO as FCF's collaborator Llewellyn.
 
^Many thanks for the positive write-up. I don't think there will be much activity without the m-OH. There certainly are more potent (and simpler) tramadol analogues, but this isn't one of them. Grunenthal & related patents certainly suggest no activity...
 
Thanks for the replies...Seems like it isn't worth following up on it due to possible scam and/or the no activity aspect. Shame.
 
2-(dimethylaminomethyl)-1-phenylcyclohexan-1-ol showed 3.3 times less analgesic activity in experiment with mice with a concomitant ~3fold drop (!) of the therapeutic index (from 24.5 to 7.1; expressed with respect to the LD50-values). In other words: It takes more material per gram to achieve a comparable analgesic effect, while at the same time putting up with increased toxic effects.

The calculation gets even more complicated because tramadol's somehow unique effects stem from the combined action of the racemate + the (again racemic) M1-metabolite, showing an interesting combination of μ,- δ- and κ-agonistic, as well as NE-reuptake activity. To my best knowledge is only the very basic analgesic data available from the animal experiments, which I cited above. Who the fuck knows how these translate into the subjectively felt for humans effects of the compound in question.


Apart from that, it definitely discredits Bluelights ADD reputation heavily to ask over and over again: "Please explain me the latest RC offers, because I have absolutely no clue what the heck they (pretend to) offer this time! Already the IUPAC-name sounds soooooo trippy... And what was 'IUPAC' again?" :\ Doh! That's so damn lame and certainly not the purpose of this forum. If there ain't more details available for a certain compound than to hell with that stuff! If you have no idea at all what to think of a certain compound, than to hell with you if you even consider a single moment to buy and ingest that stuff solely based on what folks tell you in a internet forum.

IMHO threads like this deserve to get closed immediately!
 
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Apart from that, it definitely discredits Bluelights ADD reputation heavily to ask over and over again: "Please explain me the latest RC offers, because I have absolutely no clue what the heck they (pretend to) offer this time! Already the IUPAC-name sounds soooooo trippy... And what was 'IUPAC' again?" Doh! That's so damn lame and certainly not the purpose of this forum
But this thread definitely doesn't belong to BDD or OD. ADD is just the best place to ask such questions, because all educated folks visit this part of Bluelight.
And I don't really understand how such threads discredit ADD reputation. A person asks a question, and gets qualified answer from competent people.
 
You got a pretty shitty attitude I posted this thread because I am GENUINELY interested in educating myself on the more advanced aspects of drugs and how they work.

If I wanted to get high on opioids with a 'trippy name 8)' I would go take some Oxy or something. I only wanted to know because I have tried O-Desmethyltramadol and wanted to know what the anaolg was like in comparison and get a better understanding of how it works as I am NOT a chemist.

Why is asking some one more competent than myself for some info and help a bad thing?? The only thing discrediting ADD is you...

:|

EDIT: Since I am a nice guy thanks for the info, was interesting to read. Btw 'than to hell with you if you even consider a single moment to buy and ingest that stuff solely based on what folks tell you in a internet forum' I would agree with you there all though I don't like how you phrased it, people shouldn't just eat random chems that's why it is important to find out as much as you can from people with experience which is why BL is such a good harm reduction site.
 
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Shitty attitude? I provided more hard facts with regard to the opening question than anyone else did :\ You can estimate the active dosage from these numbers with ease, well, provided that you get genuine material, which seems to be a rare exception these days. Not speaking of pure material, LOL!

I'm sorry to have sounded educative, but 9 out of 10 questions in ADD like yours are nothing else than begging to get spoon-fed with information about the latest available RC-crap. I can assure you that there is nothing more known about this material - at least not in the scientifically accessible literature, than I have told you.
Boiling and melting points were just calculated (read: completely useless), the molecular mass can be calculated by a child using the PSE, chemical formula and IUPAC-name can be derived from (free) programs or with 5 min using your brain and a basic Org Chem textbook. Summarizing, you haven't provided any viable information! NOTHING! The OP, therefore, translates for me into:
"Look what I have found! I don't know anything about, but please educate me, I wanna get high."

Where, please tell me (without getting offensive) where is the "genuinely interest in educating yourself on the more advanced aspects of drugs and how they work" in your question? I can't see it.

Why bothering with potentially harmful stuff, which will be delivered fake, or cut, or impure, or all 3 of these together. That's how the oh-so-beloved RC-market seems to work at the moment. And threads like this are nothing else than indirect advertising, further pushing this inhuman market.

That's why I wrote what I wrote before. I will remain humble and silent as soon as somebody can come up with some real data on this, resp. for similar threads in the future. Citing the rules of Bluelight's ADD:
This forum was created to discuss things which don't fit in any other. Examples of things we want to see are:

* Share something you have found in a peer-reviewed journal and present it for open discussion. A full abstract should be provided at a bare minimum. This is similar to the Drugs in the Media format.
* Review/summarize a series of at least two related peer-reviewed articles and present summaries in a "for your information" format.
* Present a "problem" that you are trying to answer. Include what you have come up with so far and ask for assistance completing the solution.
* Present accepted facts and explore what (if anything) can be extrapolated beyond what is known.
* Present two supported theories that seem to be in conflict with each other and debate the relative merits of each.
* Present any topic that you feel fit in with this forum.

While NONE of the first five points seems to get much attention recently (all of them request to give some info, too), the last one is stretched to the outmost interpretable one can imagine :(



Edit: With regard to the "EDIT" in the last post, I admit that I've indeed chosen some harsh words. My sincere apologies about that. Fact is though, that you just suggested a random chemical, most probably only inspired by the latest advertisment of a RC-vendor, which himself only ordered it from China because it was jst offered and resembles tramadol somehow. These idiots don't even know themselves what they are selling, nor do they know how pure it is, but nonetheless they keep it selling to the crowd. Stop playing the guinea pig for those fucktards, boy, where is your self-esteem?
 
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OK I admit I was overly harsh with my reply - my apologies about the 'shitty attitude' thing I just got a bit pissed off with the way you came across but on retrospect I can see why.. It did look like a 'look what I've found' thread probably because I posted late at night and was tired (plus this is my first time in ADD.) I think we just got off on the wrong foot.

Thanks again for the info though I did find it very interesting and useful. For the record I have no interest in trying the chem and it wasn't advertised anywhere I just happened to randomly come across it. If it was widely used, had studies and was well respected or just something people knew about and rated then sure I would try it most people on BL would but I don't try chemicals no-one knows about.

I'll just ignore the self esteem bit haha I've said my bit now. Once again thank you for taking the time to answer my question but please consider your words a bit more when posting (and I'll try and post more constructive threads haha.)

Take care..

EDIT: 'Where, please tell me (without getting offensive) where is the "genuinely interest in educating yourself on the more advanced aspects of drugs and how they work" in your question? I can't see it.' I'm not a chemist, I don't know too much about that kind of thing which is the reason for me asking - so I can hopefully learn even if most things go right over my head haha.

I wanted to get a bit of information so I could come back with some more questions but when it turned out everyone had already told me as much as they could I couldn't see the point in following up on it.
 
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It is not going to be more active than tramadol as an opioid. However, we dont know that it doesnt act on some other receptors etc. I remember an inventor named Liming Shao who worked for a company called Sepracor recently released a patent on the 3,4-dichlorophenyl ring substituted analogs of tramadol. These were tested for their ability to act as SNDRI type medications although the results were not impressive.

Despite what was written above about the LD50 of the plain phenyl ring compound(s) being 3 times less than for that observed with tramadol, it could still be worth a shot. Remember Shulgin tried alot of his inventions on himself. Undoubtedly there are some chemicals that you would want to steer well clear of. Nevertheless, the other side of the coin is that some self-experimentation is necessary to find out what works and what fails. I'm not advocating that people self-endanger themselves though. Maybe it's not worth the risk?
 
I seem to remember reading that phenolic & non-phenolic phenylpiperidine opioids were supposed to bind totally differently. Certainly the QSAR of the different N-substituents of ketobemidone are unlike the related ester compounds (I have not seen any work on bemidone analogues - that would be interesting).

Interesting to see that the 3,4 dichloro is once again making an appearence, Smyth. It looks like many older chemicals have had this substitution added for re-examination.
 
I seem to remember reading that phenolic & non-phenolic phenylpiperidine opioids were supposed to bind totally differently. Certainly the QSAR of the different N-substituents of ketobemidone are unlike the related ester compounds (I have not seen any work on bemidone analogues - that would be interesting).

Interesting to see that the 3,4 dichloro is once again making an appearence, Smyth. It looks like many older chemicals have had this substitution added for re-examination.
 
I know this is completely off-topic but I cant really see how to make a new thread title up to cover this. I just think that it's worth taking the time to point out that with the use of 3,4-dichlorophenyl ring or beta-naphthyl as potentiating groups, these are just two such possibilities, probably selected because of ease of synthesis considerations. In the realm of phenyltropanes it was shown that a whole variety of different halogens can be planted on the 3- and 4-positions and are well tolerated with varying effects on the 5HT/NE/DA transporter pumps. For example, the combination with the strongest affinity for the DAT was para-bromo/meta-chloro.

See here: http://en.wikipedia.org/wiki/RTI-111

I think the obsession with the 3,4-dichloro ring just stems out of ease of synthesis considerations. However, if the chemist is creative and not just bound by a low budget into making economical choices, it is easy to see from the table in the above link that one can expand the horizon to include other possibilities also.
 
THAT is really interesting. I had always thought that dichloro was the most potent. Never even thought about 3-chloro-4-bromo- substitution! Or any other dual halogen analogues. Really, really interesting!

The idea that ketobemidone binds in a mode completely different (or even substantialy different) from pethidine's seems silly to me. They're simple molecules though, so I guess it's not completely out of the picture, just really unlikely.
 
where phenyl is part of the pharmacophore substituting 3,4 dichloro or similar usually is just greasing up a molecule making this moety more hydrophobic. this almost always increases receptor affinity irrespective of the receptor or enzyme target because this hydrophobic moety is binding in a hydrophobic pocket. greasing up a lead compound is not usually that wise because even though in vitro affinity is improved a whole raft of problems appear in vivo, extended half life, annoying distribution leading to slow on slow off, induction of enzymes etc

often much more interesting is using hydrophobic groups which do not withdraw electrons, like trifluoromethoxy for example
 
The idea that ketobemidone binds in a mode completely different (or even substantialy different) from pethidine's seems silly to me. They're simple molecules though, so I guess it's not completely out of the picture, just really unlikely.

Yes, it does seem odd, but that's what was used to explain the major differences. The phenol with a ketone makes a potent drug, with an ester, moderate (1.3x meperidine) but with reversed esters, totally inactive.

Same with piperidine ring substitution & with N-substituents. All of the QSAR patterns seen in the non-phenolic analogues are thrown out of the window. The only analogues that were a stronger analgesic were the n-pentyl (and they were mixed agonist/antagonists).

I have often pondered if the secondary alcohol derivatives of ketobemidone would help elucidate the SAR of the drug. I don't think it's been researched...
 
All of this is elaborated in great depth in the numerous tramadol analog patents.

Personally i found tramadol M1 to be a good, pure agonist, very distant from tramadol proper. The more interesting question (given the sheer availability of cheap tramadol) would pertain to enzymatic or partial biosynthesis of M1 from tramadol. I have found that a 4-6 ounces of dry gin, held in the mouth with the crushed tablets, followed by another 4 ounces of gin 20 minutes later with omeprazole and tagamet makes leads to a significant increase in opioidergic activity, with decreases in monoamine activity. But a theoretically, a biosynth will work, the yields, unknown. Yet, despite of yields and only partial reactions etc, the M1 of tramadol is a enjoyable opioid, whereas tramadol is not.............Oral doses of the M1 need to be high, similar in both the potency and qualitative nature of oral meperidine. I am the one who bought out the remaining supply of the M1 from you know who, and it was truly a solid opioid, and coming from an opiosnob like me, that is a ringing endorsement..............
 
Loook at O-desmethyltramadol in the same way the prodines relate to pethedine with regard to tilidine/tilidate (a known narcotic pain killer, used in Europe). It's just the phenylpiperidine opioids with the nitrogen freed from the constraints of the piperidine ring
 
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