Diprotic Acids – 4-Acetoxy-DMT Tartrate versus HCL Salt

A question came up yesterday about whether we need to add different dose information to our 4-Acetoxy-DMT Dose Page for different salts. Our team believes that the primary salt sold over the last fifteen years of 4-Acetoxy-DMT has been the fumarate salt (fumaric acid).

If one assumed that each fumarate molecule paired up with one 4-acetoxy-dmt molecule in the salt form, then there would be about a 25% difference in the potency between the fumarate and the hydrochloride (HCl) salt. Some vendors have reportedly sold the HCl salt instead of the fumarate, and so this could result in a difference of potency between different pure salts of 4-acetoxy-DMT of about 25%.

However, after consulting with some of our friends in the Erowid Expert Network who are senior analytical and synthetic chemists, they were able to confirm that the fumarate salt of 4-acetoxy-DMT is always diprotic, with some small technical caveats.

NC writes: “Although fumaric acid itself is diprotic, its salts may not necessarily incorporate two molecules of the base. AFAIK, it is not possible to predict the stoichiometry of such compounds a priori, it all depends on whether the mono- or di-substituted fumarate remains soluble in the solvent or precipitates out. NMR would tell the story.”

  • 4-AcO hemifumarate: 304.35 g/mol
  • 4-AcO HCl: 282.77 g/mol

So there’s only a few percent different in potency between the two.

In digging around in questions related to diprotic acids and how certain we can be that any given chemical salt has a given number of freebase target molecules, PD pointed out this obscure paper:

“USP Lysergic Acid Diethylamide Tartrate (LOT 1) Authentic Substance Recharacterized for Authentication of a House Supply of Lysergide (LSD) Tartrate”. .

The paper demonstrated, via extreme drug geekery, that the two samples of pure, high grade LSD they had were not identical.

In subjecting a commercial supply of lysergide (LSD) tartrate (Sandoz Lot 79001) to authentication for adoption as a "working standard", infrared (IR) proton nuclear magnetic resonance (1H-NMR) spectra of the working standard showed some dissimilar features to those obtained from the USP LSD Tartrate Authentic Substance (Lot I).

Although comparable mas spectral results were obtained from the two LSD samples, further investigation by 1-H- and 13C-NMR spectroscopy showed the USP material to contain appreciable excess tartaric acid. 

So, according to our experts, fumaric acid is almost always diprotic, but one cannot be certain without actually verifying that with a given ‘freebase’ molecule.

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