Posts Tagged ‘ mescaline

Leminger’s Scalines

Otakar Leminger was a little-known Czechoslovakian chemist who worked for years in industry and lived on the banks of the Elbe River in Ústí north of Prague. When he retired in the early 1970s he published a paper entitled “A Contribution to the Chemistry of Alkoxylated Phenethylamines” in which he describes the synthesis of several novel phenethylamines which he tested on himself to determine activity.

(1) allylescaline, 3,5-dimethoxy-4-allyloxy-phenethylamine (2) proscaline, 3,5-dimethoxy-4-n-propoxy-phenethylamine (3) escaline, 3,5-dimethoxy-4-ethoxy-phenethylamine (4) MAPEA, 3-methoxy-4-allyloxy-phenethylamine (5) MEPEA, 3-methoxy-4-ethoxy-phenethylamine

We can classify the compounds he discussed into two groups depending on the number of ring substitutions. Allylescaline, proscaline, and escaline have three while MAPEA and MEPEA have two. Generally phenethylamines with two ring substitutions are not active, but Leminger had found some exceptions. This knowledge might have been lost to time if not for the fact that Stanislov Wistupkin brought the paper to the attention of Alexander Shulgin.

[MAPEA and MEPEA are some] of the few phenethylamines with only two substituents that show even a hint of central activity. And there is an interesting story attached. I got a call out of absolutely nowhere, from a Stanislov Wistupkin, that he had discovered a number of new psychedelic drugs which he would like to share with me. They were simple phenethylamines, one with an ethoxy group at the 4-position, and one with an allyloxy group there. Both, he said, were mood elevators active between 100 and 300 milligrams. One of them was a material called MEPEA, and the other one was 3-methoxy-4-allyloxyphenethylamine, or MAPEA. When I did meet him in person, he gave me a most remarkable publication which had been authored some ten years earlier, by a person named Leminger, now dead. It was all in Czech, but quite unmistakably, right there on the third page, were the structures of MEPEA and MAPEA, and the statement that they were active at between 100 and 300 milligrams.

– Alexander Shulgin

MAPEA and MEPEA are only mildly active and interesting mostly in the sense that they appear to be the exception to the rule that phenethylamines with two ring substitutions are inactive. Leminger also created several mescaline variants with three ring substitutions by modifying the methoxy group at the 4 position and replacing it with an allyloxy, propoxy, or ethoxy group. The resulting compounds allylescaline, proscaline, and escaline were then tested on himself and found to be much more potent and intriguing.

Physiological effects of the compounds were examined only approximately on my body. The sulphate salts of MEPEA and MAPEA in doses 0.1-0.3 g were mild mood-elevators and were also cough calming agents. Allylescaline, proscaline, and escaline were much more active. Qualitatively there wasn’t a big difference among them and quantitatively their effect decreased: allylescaline was more potent than proscaline, and proscaline more potent than escaline. As an example the allylescaline experience is described:

“One hour after a 20 mg dose of allylescaline: perhaps slight vertigo, light drunkeness and pleasant excitation with locomotion need was observed. Eye perceptions were pricked up, colours seemed to be more warm and objects more plastic. Surroundings were much more interesting than usual. Colourful hallucinations were observed in the dark. Moreover, a calming effect to the breathing system and some kind of constriction of the digestive system was observed. Sleep at night was restless with megalomaniacal fantasies. Even 12 h after administration the effects were present. More serious studies of physiological activity are in contemplation.”

– Otakar Leminger

Leminger was the first to synthesize and consume allylescaline, the most potent of the mescaline derivatives explored. He was able to identify active phenethyamines with only two ring substitutions, a notoriously unproductive class of compounds. Did he conduct additional experimentation and screening beyond that detailed in this paper? No other publications by Leminger relating to psychedelic compounds are known.

Might there be other treasures that he had discovered, and never published? Was young Wistupkin a student of his? Are there unrecognized notes of Otakar Leminger sitting in some farm house attic in Northern Czechoslovakia? I extend my heartfelt salute to an almost unknown explorer in the psychedelic drug area.

– Alexander Shulgin

Otakar Leminger, A Contribution to the Chemistry of Alkoxylated Phenethylamines – Part 2. Chemicky Prumysl 22, 553 (1972).

Alexander Shulgin, #2 Allylescaline. Phenethylamines I Have Known and Loved, Transform Press (1991).

Alexander Shulgin, #123 MEPEA. Phenethylamines I Have Known and Loved, Transform Press (1991).

Psychedelics in the Public Consciousness

Google Ngram is a very interesting project which measures the frequency of the occurrence of words in a large body of books published over the last several hundred years. This can be considered somewhat as a measure of public awareness of a certain term, so let’s use it to see how various prominent psychedelic compounds (mescaline, LSD, psilocybin, and MDMA) have risen and fallen in the public consciousness from 1900 to 2000.

The first thing we see is that psychedelic compounds as a whole are a very new concept, entering popular usage only in the middle of the 20th century with knowledge becoming more widespread in the 1960s. The word LSD has an almost overwhelming frequency of use, reflecting the intimate association of the drug with the popular concept of the psychedelic experience. Switching this out for “lysergic acid diethylamide” should allow us to compare relative trends with other psychedelic compounds due to decreased frequency while still maintaining a sensible relation to the original term.

This normalizes the dataset somewhat.

Mescaline had been used for thousands of years until it was first isolated and identified in 1897. It slowly grew in the public consciousness until Aldous Huxley’s 1954 work The Doors of Perception thrust the compound into the mainstream.  
LSD (lysergic acid diethylamide) was first consumed by Albert Hofmann in 1943, initially introduced to the market as a psychiatic drug in 1947, and its potential became more clear with corporate and government experiments during the 1950s including the infamous Project MKULTRA. High potency and its positive character led to efficient distribution and widespread use in the 1960s.  
Psilocybin is another ancient compound with sacramental use spanning thousands of years. Vice President of J.P. Morgan and amateur mycologist R. Gordon Wasson travelled to a remote village of Mexico on a rumor that their religion included ingestion of mushrooms. In 1957, he published an article in Life magazine entitled Seeking the Magic Mushroom that did for psilocybin what Huxley did for mescaline.  
MDMA was first synthesized in 1912, but it languished in obscurity until the mid-1970s when Alexander Shulgin, then at University of California, heard from his students about unusual effects of the amphetamine derivative. In 1978 he and David Nichols published the first report on the drug’s psychotropic effect in humans and its use spread among the psychiatric community as an adjunct to therapy. MDMA used in a recreational context was first reported in gay nightclubs in the Dallas area in the early 1980s with usage peaking during the 1990s rave scene.  

Other trends become apparent when we separate our observations geographically. While the opportunity to do this is necessarily limited due to language restrictions, we can compare American English usage with British English usage quite easily from 1950 to 2000.

We can see that MDMA citations peaked in the mid 1990s in American English as the British rave scene made noise in North America, but the trend faded in the US while use continued to climb in British English.