ALTERING THE DXM MOLECULE IN A WAY NOBODY EVER HAS BEFORE by James Clayton Roberts The following section is a first for the DXM community - altering the DXM molecule in ways that have never been attempted to my knowledge, and altering it in such a way that could change the way we view DXM forever. Just like with tryptamines, there are many possible and endless variations and derivatives that can be synthesized. James Clayton Roberts, who is 34 years of age, is attempting to do something that will be groundbreaking to say the least. Some of the information is technical and if you are not well versed in organic chemistry, may even be hard to follow. I have added my own notes, where necessary, to try to bring things in perspective for a beginner. It is also not suggested you try any of this without consulting Mr. Roberts first, as he is a professional and knows what he is doing. I plan to bring future updates with each new issue of this zine to bring you up-to-date on these remarkable possibilities. Introduction: What would happen if you inserted an iodine atom into DXM? Is it possible? What would the effects and ensuing molecular structure be? We will attempt to answer some of these exciting questions in this article. There is actually a simple, cheap synthesis on Rhodium's drug chemistry archive for inserting an iodine atom into a methoxy amphetamine. It uses only alcohol, silver sulfate, and iodine. In theory, this will work with the DXM molecule because DXM has a methoxy group on it's benzene ring as well. It kind of follows the model of phenethylamines. In fact I predict that iodo-DXM will be very potent and with much weirder effects. Change-the-world-type-stuff. And you read it here first! [ Editor's Note: Iodine is the least active member of the halogen family - at room temperature, it is a solid and consists of purplish-black crystals. It would probably the the most difficult chemical to get because it is used in meth synthesis. Silver sulfate can be expensive, but it can also be made, which would probably be a better route to go if you're low on funds.] More on the Methoxy Group Most psychedelics have a methoxy group. As far as inserting the iodine atom, 4-iodo 2,5 dimethoxy amphetamine and phenethylamine seem rather potent, so there's no reason why iodo-DXM wouldn't be. Other drugs that this type of substitution would work on would be Methoxy-tryptamines, but certain synthesis examples for melatonergic drugs suggest that the iodine might end up at the 2-position, which, nevertheless makes the melatonin derivatives more competitive for the melatonin receptor. Methoxy phenylpiperazines would also be a candidate for substitution with iodine using this method. If anyone does try it before I get the chance, I suggest starting at less than 0.5 mg, as Shulgin did with certain tryptamines. Other Ways to Change the DXM Molecule I wouldn't mind sticking some alkyl groups on there somewhere, or changing the methoxy to methallyloxy. See Shulgin's PIHKAL reference for the methallyloxy phenethylamine or amphetamine derivative - "I am surrounded by unreality. Much too much too much." It's too bad the methoxy group and open positions on the benzene ring are the only amenable places for change. Changing the methyl on the nitrogen to a longer group might be interesting. Iodination of methoxy opiates might be a possibility with this method I mentioned, with an attendant increase in potency and changes in effects. The methyl group on the oxygen could be removed by boiling DXM free base in phosphoric acid for three days or with concentrated HCL under reduced pressure for less time. Then, heating with an alkyl halide and a base.
Figure one shows where the iodine atom can go to on the DXM molecule (the benzene ring). The DXM would have to be converted to the free base first, but this is relatively simple and there are formulas on the web for that. Other possibilities include the use of liquid chlorine to plant a chlorine atom on the ring (see PIHKAL for an example), or the use of N--bromo succinimide. If you plant a chlorine atom on the ring the resulting chemical would be chloro-DXM . N--bromo succinimide is a brominating agent, used to add bromine to benzene rings. The resulting chemical from that synthesis would be bromo-DXM .
Figure two shows the other point for possible change, the methoxy group. Removing the methyl group from the oxygen can be done in one of two (or more) ways. First, and more difficult, is to boil, or reflux the DXM free base in concentrated phosphoric acid for 72 hours, then neutralize the acid with an alkali hydroxide, like sodium hydroxide (lye), or ammonia solution, then extract with an organic solvent. This comes from a book called Recreational Drugs , by Professor Buzz. It is a quantitative chemical technique, called a methoxyl determination, used to discern the composition of a material. The book, by the way, that section deals with the making of DXM's levo isomer, Levo-Dromoran, a potent opiate.
Figure three shows the results of removing the methoxy group. From there a number of things can be done. The dextrorphan can be refluxed with acetic or butyric anhydride to make the corresponding alkyloxy derivatives. This is the manner in which heroin is made from morphine. It takes about 72 hours. O-acetyl dextrorphan should be very potent. The active principle here is that acetylating it makes it more fat soluble, thus it gets into the system better and faster. Note the differences in potency between morphine and heroin. A more fat-soluble drug is called lipophilic (fat-loving), while a water-soluble drug is called hydrophilic (water loving). The other thing that can be done with the hydroxy group is to stick an alkyl group onto it. These rections are somewhat analogous to those found in TIHKAL for the N-alkylation of tryptamine (making DMT, DET or DIPT from tryptamine). The Dextrorphan free base is heated with an alkyl halide (methyl-, ethyl- or propyl- bromide or iodide) and a base which is a stronger base than the Dextrorphan in a solvent. The separation of the product from the reaction mixture is also largely analogous to the aforementioned references. The bromine or iodine atom leaves the alkyl halide and bonds to the stronger base, while the alkyl part joins to the oxygen. Dextromethorphan can be made this way from Dextrorphan. Once you are familiar with the reaction, the derivatives that can be had are limited in number only by one's imagination, the facts of organic synthesis, and one's funds for and the availability of alkyl halides of differing structures. Alkyl halides that contain oxygen, or sulfur in ring systems, can also be used, and some of this can be seen in the reactions outlined in PIHKAL and TIHKAL by Alexander Shulgin. Some synthesis of this kind will fail, but I have a strong belief based on the literature that more will succeed than fail. Other alternatives that involve more expensive, difficult to handle or suspicious reagents include the use of sodium alkylates, like sodium ethylate, and organic sulfates, like propyl sulfate. It is important to remember that these are general methods that can be adapted to other compounds which have a benzene ring with a methoxy group attached to it. Finally, there are other ways to alter the DXM molecule. If you remove the methyl group from the oxygen atom and replace it with another group, you would change the name from dexro*meth*orphan to say, dextroethorphan (ethyl) or dextroproporphan (propyl) or dextrobutorphan (butyl). Each should have a somewhat different profile of activity. Conclusion There is still yet a lot of research to be done in this field. To put things in perspective, look at all the tryptamine derivatives there have been, and think of how potent and different they all are. Now apply this to DXM and you have an endless sea of possiblities, with only your own imagination being the limit