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Is methoxetamine chiral?

Yes, it contains one stereocenter. Thus it exists as two enantiomers. Commonly available methoxetamine is a racemic mixture as far as Im aware.
 
Is there any word AT ALL as to what mixture produces ideal effects? For the life of me I can not get a clear answer to this.
 
Define "ideal".

All MXE that has been sold so far has been racemic so nobody would know.
 
Maybe take a look at the Ketamine Isomers Subthread in PD (via navigation of: the Psychedelic Index >> Ketamine), then extrapolate what you read there to methoxetamine and take a guess at which isomer does the most reuptake inhibiting or which one would be more purely dissociative. It may turn out that even classical dissociation is comprised of more than one component (cognitive, proprioceptive, existential, ...)

285px-Methoxetamine.png


The chiral carbon is the one represented by the vertex (point / corner) immediately left of the N(itrogen). Why? Because 4 things attached to that one are NOT interexchangable. Which makes it an asymmetrical locus.

I wonder... is all it takes to separate MXE isomers precipitation with a pure tartaric acid enantiomer?
 
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That's how I did it.

I only tried one isomer so far, and the procedure was very imprecise, but it seemed considerably less potent than normal.

This was accounting for the fact it was the tartarate and contained precipitated NaCl so it seems like it was quite successful.

The procedure was quite a lot of hassle and I've not tried it again since because I enjoyed MXE so much on its own.



NB the synthesis of MXE produces a perfect 50/50 mix so this phenomenon cannot be used to explain the low potency of your batch of MXE, dear reader.
 
Cool man! But wait what, you haven't saved the other isomer? Just like with the getting rid of NaCl, A/B extraction seems like the logical work-up...
But yeah even if that is true, being an arm-chair chemist is easier. :)
 
I forget why the other isomer wasn't viable for results (a measurement issue IIRC) but what was left was tried by other subjects who thought it was more potent.
 
I am sorry for opening this thread again, but I have just come across this discussion and would like to ask @Transform if you have been able to successfully separate the enantiomers of Methoxetamine. If so, which chiral derivatisation agent did you use, if I may ask?
I haven't found any publication about chiral separation of MXE using LC- or GC-MS. Does anyone know of any?
 
We used d-tartaric acid. We did not verify the selectivity of the recrystallisation but subjectively there did appear to be a difference.
 
Pretty sure the answer to that is L-(+)-tartaric acid which is also used a lot in brewing / winemaking. It is a substance used for separating isomers of various compounds, also like amphetamine for example.

As long as there is a significant difference in how (energy efficiently) this tartaric acid isomer forms salts with the isomers of a drug, you should see that as a difference in tendency to crystallize... allowing you to crystallize one isomer of the drug first and the other one after that, after as in under changed conditions like cooled or evaporated or further addition of a second solvent.
Depending on how big that difference is though, and how well you are able to use the correct solvent systems etc... achieving that separate crystallization may range from doable to quite difficult.

What I don't really know is which MXE isomer would crystallize with L-(+)-tartaric acid, I suspect that it's the levo with the levo for point-symmetry.

You don't use LC or GC-MS for chiral separation I don't think, as the physical properties involved with that are not different for the isomers? A polarimeter though can tell you the optical activity.

EDIT: oh the dextro was used... well I guess same story applies, only the levo should be more available?

I wonder, was there a marked gap between when one isomer crystallized and stopped crystallizing, and then the other under changed conditions? Or was it more continuous? If continuous, I guess it would be very hard to really be useful.

Anyway.... with most drugs who would be bothered to isolate the solely active isomer?... but with something like amphetamine or certain dissociatives where the other isomer also has activity but different... then you more or less just have two different drugs that may be worth experiencing by themselves! Something possibly overlooked with analogues of these substances, to be fair we probably often just don't know about the different activity with novel analogues.
 
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If you did not use LC for the separation, but this crystallisation procedure, I wonder if you could tell me where you found the procedure or whether you could tell me the procedure and what I would need?
 
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