smiley (Junior Member)
01-19-00 00:30
No 105788
      DXM -> DXO conversion  Bookmark   

One can convert by demethylazation dextromethorphan hydrobromide (DXM HBr) to dextrorphan (DXO) by refluxing it with an acid (e.g. citric acid) in an ethanol solution (e.g. vodka).

Now, if one were to use this method with, say 10g DXM and 10g citric acid powder does anyone know answers to any of the following?

a.) What the resulting salt of DXO would be?  Would it be Hydrobromide or maybe Hydrocitrate? 

b.) If one were to attempt to evaporate the solution I assume they would be left with a mixture of a DXO salt and excess citric acid powder.  I assume there would be an equal number of mols of DXO as there was DXM but since the DXO and citric acid were all "mixed up" would that make accurate measurement of DXO impossible?  Would the only way to accurately measure be to leave in solution?

c.) What actually "happens" to the methyl of the DXM in this reaction?

Thanks anyone

    Methamphibian man
01-19-00 13:15
No 105789
      Re: DXM -> DXO conversion  Bookmark   

Why would you want to do that? the body already converts DXM to DXO. Do you, or any other bees know of any way to convert DXM HBr into the freebase form?
(Junior Member)
01-19-00 15:25
No 105790
      Re: DXM -> DXO conversion  Bookmark   

The body is somewhat inefficient at converting it to DXO when taken orally.  A significant percentage remains DXM which has its own psychoactive effects.
01-26-00 03:54
No 105791
      Re: DXM -> DXO conversion  Bookmark   

The infamous DXM faq says one can do a simple a/b on dxm hbr providing there isn't any other active ingrediants in the cough syrup that would convert too.  So, dissolve dxm hbr in a few ml of dh20.  Add some n/p like toluene, xylene.  Place in a sep funnel and add 10% NaOH solution equal to the amount of original dxm hbr solution.   Shake, allow separation.  Freebase DXM moves into the n/p solvent.  Seperate layers, maybe extracting with n/p once or twice more and collecting.  Distill off or evap and viola', DXM freebase.  Other than getting this out of a cough syrup gunk however, why would you want this?  It's not considered smokable.  Of course there is the bromine poisoning from prolonged exposure.   I dunno, 30mg of pure DXM hbr in capsule with vitamin C or somesuch suppresses my coughs just fine, and I don't get cough attacks often enough to worry about that kind of accumulation. 
(Junior Member)
01-26-00 10:42
No 105792
      Re: DXM -> DXO conversion  Bookmark   

The intent was not to create DXM freebase, but rather DXO (freebase or salt).  The effects of DXO alone are (theoretically at least) more similar to ketamine than DXM (which is (only) partially metabolized into DXO).
01-28-00 19:46
No 105793
      Re: DXM -> DXO conversion  Bookmark   

Really, don't smoke the stuff at all. A friend (no, really) did it and had a small amount of blood spotted mucous on his pillow case he coughed up whilst he slept  (so much for the cough suppressant properties, eh?). Not to mention the burning in his throat and complaints of NASTY taste.
06-27-02 08:53
No 325958
      Citric acid won't do the trick  Bookmark   

Totally incorrect.  You cannot cleave the methyl group with citric acid.  You have to use excess HBr or HI on a phenyl ether to produce an alkyl halide and a phenol.  In terms of reactivity toward the cleavage of ethers, the hydrohalic acids are as follows:

HI > HBr >> HCl

I didn't think that HBr could do it but apparently the bromide ion is a good enough nucleophile.  Citric acid and the like are much weaker nucleophiles than hydrochloric acid so there's no way in hell they could cleave the methyl group.

The reaction occurs as such (I'll use hydroiodic acid as the example):

[DXO]-  Means the rest of the DXO molecule, with whatever is attatched to the 3 spot (the phenolic bond) represented externally.
(so "[DXO]-OCH3" would actually be DXM and "[DXO]-OH" is actually DXO)

The reaction takes place in excess HI.

1)  The oxygen attatched to the phenyl group becomes protonated.


2)  Transition state:  The bromide ion starts forming a bond with the methyl carbon atom and the bond between the methyl carbon and the oxygen begin to break.

[DXO]-O- - -CH3

3)  The reaction is completed, leaving DXO and iodomethane.

CH3I +


There are two practical applications of converting DXM to DXO:

1) It seems that many people find a high ratio of DXM to DXO unpleasant, so in this way the ratio could be controlled.

2) CYP2D6 individuals cannot tolerate DXM because they cannot efficiently convert DXM to DXO and are left with a high ratio of DXM to DXO.  This would give those individuals a chance to enjoy the drug.

The other application would be for the DXM enthusiast to explore different ratios of each substance and report on the differences between each chemical.
(PVC-Analog Taste-Tester)
06-27-02 22:25
No 326199
      "The effects of DXO alone are (theoretically at ...  Bookmark   

"The effects of DXO alone are (theoretically at least) more similar to ketamine than DXM"

  To be honest with you, my first reaction is to say that claim is bull-shit. DXM has always given me a tooth-grinding, anxiety-filled, hellish experience. With ketamine, sometimes I have an experience that makes me feel psychologically raped, but at least I always gain wisdom. Ketamine is so much deeper. Shit, I wish DXO was like K! But, I highly doubt it! 

Love my country, fear my government.
06-28-02 01:26
No 326279
      bah  Bookmark   

Everyone's experiences are different.  I have three friends, two of whom who love DXM and one who's relatively indifferent to it, but they all say it's very similar to K.

I think the poster meant in terms of DXO's binding sites though...