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Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT. 
“Mescaline analogs: substitutions at the 4-position”. 
NIDA Res Monogr. 1978;? (22):27-37.
Mescaline, 3,4,5- trimethoxyphenethylamine, is one of the longest known and best studied of the psychotomimetic drugs. It has served as the structural paradigm for the synthesis and study of a large number of analogs. Many of the molecular changes have resulted in increased potency, and have established structural parameters felt to be necessary for maximum neurotoxic activity. One of these is the extension of the carbon chain from two carbons to three, by the addition of an alpha-methyl group adjacent to the basic nitrogen. This simple homologation appears to protect the nitrogen atom from metabolic removal, and to effectively increase the potency of the drug. In the examples in the earlier literature where direct comparisons between the two-carbon and the three-carbon counterparts were made, there was certainly an increase in potency. However, the metabolic argument is clouded by the fact that in those examples where the chain was extended to four carbons providing as complete a structural hindrance to metabolic attack as a three-carbon chain there was also a consistent decrease in biological activity.
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