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An Unpleasant Exploration of DXO
by Student, Summer 2001
html & archived by erowid Sep 15, 2001

Overview of Experiment

I once read in a FAQ that DXM (dextromethorphan) is metabolized to DXO (dextrorphan) by removal of the phenolic methyl group, and that the psychoactivity of DXM may be influenced or enhanced by the presence of DXO formed from it.

I have ingested DXM HBr in doses up to 960 mg (I weigh about 70 kg), but could identify the effects of doses as small as 60 mg. I synthesized and consumed DXO as a way to distinguish its effects alone from those of DXM. The synthesis and effects are described below. The psychological effects were subtle (almost imperceptible) and very disappointing, unlike the effects I would expect from comparable doses of DXM. The physical effects, on the other hand, were alarming, and my main motivation in providing this report is to spare others from experiencing them unprepared.

Side Effects

The first main physical effect was intense overall itching, which others have reported with DXM but which I had never experienced at all over many DXM trips. This was entirely gone after a few hours, and isn't my main concern. The other effect was a sound like a low thudding or rushing which was present d uring the experience, but recurred with less and less frequency over the following months and years.

It is now four years later and I haven't noticed the sound for a long time. I couldn't tell at the time if the sound was coming from outside of me or not, but it seemed to follow me and I concluded that the circulation in my head had been changed to become audible, perhaps by a change in blood pressure.

These effects of DXO which didn't occur during DXM trips may be due to a higher peak level or a more rapidly increasing blood level of DXO. Unlike directly ingested DXO, the DXO formed in a DXM trip is slowly generated in the liver and is being disposed of meanwhile. There is always the possibility that the DXO wasn't pure enough, but it was pure by TLC analysis and if a mere trace of side product produced these effects then it is very toxic and makes DXO synthesis perilous.

DXO Synthesis:

There have been other syntheses posted on the net. These have used citric or hydrochloric acid (HCl) and water to cleave the phenolic ether bond in DXM, but such a reaction won't work on this type of ether - check almost any college organic text. It isn't that HCl isn't a strong enough acid, but that a good nucleophile must also be present and chloride is a poor nucleophile. The nucleophile is what attaches to the unwanted methyl group and carries it away, leaving DXO behind. The reaction looks like this:

M-O-Methyl(DXM, dissolved) + HX(dissolved) --> M-OH(DXO, dissolved) + X-Methyl(Gas)
(Where M is most of the DXM molecule and X = bromide or iodide)

Bromide is a good nucleophile and iodide is a very good nucleophile. Therefore hydrobromic acid (hydrogen bromide, HBr) or hydriodic acid (hydrogen iodide, HI) will work. The bromide or iodide can also come from a salt (like sodium bromide below) as long as a strong acid is also present. Why the authors report that their concoctions have different effects than DXM I can't explain. The third experience below took place in my bed during the night. I had anticipated effects similar to or milder than a moderately intense DXM trip, and so hadn't made any special preparations. As I recall the experience lasted 6-8 hours.

Reflux (boil, returning the cooled, liquefied vapor back to the boiling liquid) one gram of DXM HCl (mp. 186-193 dec., isolated from cough syrup) in a mixture of concentrated hydrochloric acid (15 mL) and a saturated solution of sodium bromide dihydrate (5.13 g) for 22 hours. Cool, add water, extract (shake) with methylene chloride, discard the organic layer (on the bottom), and basify (make blue on litmus paper) the aqueous layer with potassium hydroxide. Extract the aqueous layer again with methylene chloride and discard the extract. (This removes non-phenols, such as unreacted DXM) Acidify (make red on litmus paper) the aqueous layer with HCl and make it neutral (between blue and red on litmus paper) with sodium bicarbonate. Extract with methylene chloride, dry (shake) the extract with sodium sulfate, and evaporate it.

More effective is to reflux the DXM in 57% hydriodic acid for one hour, followed by the above work up. The product dissolved poorly in petroleum ether but fine in ethyl acetate.

Elute DXO from a 2 cm wide by 9 cm tall column of activity I basic alumina using 50 mL methylene chloride, 50 mL of 1% methanol/methylene chloride, and 100 mL of 2% methanol/methylene chloride. (This purifies the DXO) Colorless product comes out just ahead of an orange band. mp 198.5-199.5 (corr.) Lit. (Merck) 198-199. The product weighs 1.10 g.

DXO effects:

50 mg DXO had little effect.

Took 150 mg of DXO base as powder orally. Feel sudden itching in one hand - it goes away. Feel relaxed, receptive, clear headed. I notice that I'm patient, in contrast to my usual restlessness - very valuable demonstration. I want to be patient like that the rest of the time. Easy on the body, no fatigue later on.

1.10 g - (.05 g first dose + .15 g second dose + .56 g remaining) = .34 g third dose

12:30AM Took 340 mg of DXO base as powder orally. There was an alert after 45 minutes, and then over the next few hours an intense itching and mild flushing came over my hands, temples, groin, arms, feet, and legs in that order. It would have been much worse if I hadn't ignored it and laid still.

Fortunately I managed to fall asleep. During this time there was also a deep droning which pulsated with my heart, and it would go away for short times. Psychologically I felt sedated but alert, and meditation was easier, and I was more patient, which made the very unpleasant itching tolerable. The itching wasn't painful but it lasted too long and wore down my patience.

I felt peaceful but emotionally dead - the opposite of the harmala alkaloids. Dreams were a little more vivid and strange during the next four hours, and the itching was gone when I awoke but the droning remains as the only effect - along with warnings of a possible headache.

My anal sphincter hurts too - no explanation. No headache. Felt energetic and peaceful for the first half of the day, then worn out the second half. The droning has come back every night for the last two weeks. It comes and fades away with no apparent pattern.