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Author: Subject: Dxm chemistry
njl
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[*] posted on 1-12-2020 at 11:56
Dxm chemistry


I have recently come into possession of a few grams of dextromethorphan freebase for reasons irrelevant to this thread. I personally have no interest in dxm recreationally so I'm looking for something to do with it. As far as I know its chemistry isn't very interesting. I'm not necessarily looking for active compounds to make (although I'm not opposed) so if anyone can think of something to do with it a reply would be greatly appreciated.
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[*] posted on 1-12-2020 at 20:26


How about ether cleavage to get a phenol, then Williamson ether synthesis with various alkyl bromide to get different analogues like ethoxy, propoxy, etc? Would they be psychotropic active too?



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njl
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[*] posted on 2-12-2020 at 06:53


Honestly, I think the ether is the only good starting point since there isn't really any other area where a selective reaction could take place. Just the demethylated analogue (dextrorphan) is IMO better than straight DXM but I'd like to do something a bit more interesting than that. Modifications to the C and D ring would be cool, but again I don't see any way to selectively do anything.
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[*] posted on 3-12-2020 at 00:20


I don't know how feasible it is but you could try a Hofmann degredation to try to invert the nitrogen bridge to form the other isomer. Way back when, when they were testing out DXM and Levorphanol's chemical structure they would use destructive measures to make downstream products that were already known and characterized. I think they made phenanthrene or some sort of derivative to prove it's chemical structure

[Edited on 3-12-2020 by Opylation]
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njl
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[*] posted on 3-12-2020 at 07:05


I'm not personally familiar with the Hofmann degradation but I don't see how that reaction would apply to a substrate like dextromethorphan. Could you elaborate?
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[*] posted on 3-12-2020 at 08:34


DXM has a tertiary amine making up part of the D-ring. Hofmann degradation cleaves that ring forming a tertiary amine (dimethylalkyl amine) from DXM. It's been awhile since I've looked at the actual process with DXM but I'm sure if you looked up the procedure along with DXM you could find some hits
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[*] posted on 3-12-2020 at 09:43


Could you be talking about the Hofmann *elimination*? Because dxm could work as a substrate here, but I can't find any info on this and I don't see how that could lead to isomerization.
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[*] posted on 3-12-2020 at 10:08


ah you're right. I always mix up the names of the two. When I think about them both I think of Hoffman rearrangement and Hoffman Degradation, but that's one of the same. Not the first time either. Yes, I meant Hofmann elimination

I haven't actually came across any literature from start to end that details a procedure regarding isomerization of DXM to its levo counterpart. I was just thinking back to when I was reading an organic synthesis textbook that mentioned synthesis of old medicines and listed their structural proofs. I'm not really sure its feasible to be honest, just throwing out ideas. I'm pretty sure the book only showed them making phenanthrene from it as their proof

[Edited on 3-12-2020 by Opylation]
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[*] posted on 4-1-2021 at 17:24


Imo bromination of the Benzene ring. followed by hydrolysis, and then the Williams ether synthesis with your alkyl halide of choice or possibly acetylate with acetic anhydride and then possibly see if it's active. their is a varity of different products you can get so it might also be interesting to get it tested to see at which position it is halogenated at. But of course there's probably no procedure directly related to this so you would have to make one up yourself.
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[*] posted on 4-1-2021 at 17:26


Use it as phase transfer catalyst in oxidation of benzyl alcohol to benzaldehyde with aqueous nitrate salt. Pretty high yielding (83+%)
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