Alpha-D, or α-D, also known as 3,4,5-trimethoxy-α,α-dideuterophenethylamine or as α,α-dideuteromescaline, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. "The 4-D and the β-D are two of five obvious deuterium isomer derivatives of mescaline. The three remaining are: (1) 3,5-D (4-methoxy-3,5-bis-trideuteromethoxyphenethylamine); (2) 2,6-D (2,6-dideutero-3,4,5-trimethoxyphenethylamine); and (3) α-D (α,α-dideutero-3,4,5-trimethoxyphenethylamine). I fully expect both 3,5-D and 2,6-D to be indistinguishable from mescaline in effect, since it is known that not much metabolism takes place in man at these locations of the molecule. The last compound, α-D, could be quite a different matter. The principal metabolite of mescaline is 3,4,5-trimethoxyphenylacetic acid, and this product requires enzymatic attack at the exact position where the deuteriums will be located. To the extent that they are harder to remove (come off more slowly or to a lesser degree), to that extent the molecule will be more potent in man, and the dosage required for effects will be less. The compound will be easily made by the reduction of 3,4,5-trimethoxyphenylacetonitrile with lithium aluminum deuteride. And if there is a believable difference between α-D and mescaline, it will be necessary to synthesize each of the two optically active α-mono-deutero analogs. That will be quite a challenge." It is the isotopologue of mescaline in which the two hydrogen atoms at the α position have been replaced with the deuterium isotopes.
According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, α-D had not yet been synthesized or tested, but would be expected to have similar properties and effects to those of mescaline. However, it would be expected to have reduced metabolism via deamination than mescaline, which may result in some degree of greater potency in comparison. Subsequently, Daniel Trachsel reported in his book Phenethylamine: von der Struktur zur Funktion (Phenethylamines: From Structure to Function), based on anonymous personal communication in 2009, that α-D is active at a dose of 230mg orally, with substantial effects similar to those of a 320mg dose of mescaline in the same subject. As such, α-D may be approximately one-third more potent than mescaline. This is consistent with approximately one-third of a dose of mescaline being excreted as the deaminated inactive metabolite 3,4,5-trimethoxyphenylacetic acid (TMPAA) in humans.
The chemical synthesis of α-D has been described. Analogues of α-D include β-D (beta-D; β,β-dideuteromescaline), α,β-D (alpha,beta-D; α,β-dideuteromescaline), and 4-D (4-trideuteromescaline), among others.
α-D was described by Shulgin in PiHKAL in 1991 and in subsequent publications. Later, Trachsel further described α-D and its properties in humans in 2013. The drug does not seem to be a controlled substance in Canada as of 2025.
See also Scaline β-D (β,β-dideuteromescaline) α,β-D (α,β-dideuteromescaline) 4-D (4-trideuteromescaline) Deumescaline α,α-Dideuterophenethylamine
References
External links α,α-Dideuteromescaline - Isomer Design