Synthetic Compounds Similar to Mescaline

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Image retrieved on March 28th, 2014.
Image retrieved from on March 28th, 2014.
Image retrieved from on March 28th, 2014.

The mescaline molecule is the simplest of the b-phenethylamines. Hundreds, if not thousands, of similar compounds have been synthesized in laboratories. These compounds bear a chemical structure that resembles ephedrine, which in the 1920s was “the primary reference standard” for stimulatory action in the central nervous system.
Gordon Alles, a pharmacologist associated with the Medical School of the University of California in Los Angeles and the initial sponsor of Edward Anderson's peyote studies, was very interested in this area of chemistry and eventually synthesized a number of psychoactive compounds that have chemical structures similar to that of mescaline. The best known of these are amphetamine and MDA. His discoveries inspired further investigations that led to the creation of quite a number of “one-ring” substituted phenylisopropylamines, which look much like mescaline on the molecular level but so far rarely have been found in the natural world. Many of these compounds will be discussed in Chapter Five.
Five compounds are identical to mescaline except for modification at one point on the molecules ring, but these are expensive to make and so far have been experienced by only a few people.



Escaline and proscaline are the best known of these analogues and differ from mescaline only in that methyl group in the 4-position on the ring has been replaced by an ethyl or by a propyl group. Both compounds, in Shulgins words, “appear to be qualitatively indistinguishable from mescaline in their action.” There are two main differences: these “substituted” compounds cause less nausea than mescaline and are active in dosages of 40-80 mg., and thus exhibit about a five-fold increase in potency.
Also synthesized are 2-6-dichloral-TMPEA (trimethoxy-b-phenethylamine) and 2-chloral-TMPEA—these are the 2,6-dichloral and 2-dichloral analogues of mescaline—and 4-thiomescaline, a compound in which a sulfur atom replaces oxygen in the 4-position. The last has been found to affect central nervous system. In the Journal of Psychedelic Drugs for January-June 1979, Shulgin discusses escaline and procscaline, and makes this important note on the sulfured variant:

It is active in humans at 10-25 mg so it represents a 12-fold increase in potency over mescaline. Of all the compounds mentioned in this review, it comes most closely to being what should properly be called a psychototomimetic. It produces a very intense and disorganized psychotic state that has some aspects of visual distortion about primarily disrupts the mental integrity.

pp. 131-133 Psychedelic Encyclopedia by Peter Stafford (1983)