Mescaline
Mescaline is an alkaloid from the group of phenylethylamines with hallucinogenic properties. Its systematic name is 2-(3,4,5-trimethoxyphenyl)ethanamine, but it is also known as 3,4,5-trimethoxy-β-phenylethylamine. It is the main alkaloid of peyote cacti (Lophophora williamsii) and San Pedro cacti (Echinopsis pachanoi, Echinopsis peruviana). Culturally, its importance is limited to the entheogenic effects it generates in people, however it has potential medical applications of great relevance in fields such as psychology and psychiatry, as well as in molecular research on the etiological mechanisms of schizophrenia.
History
In 1897 Arthur Heffter, a German pharmacologist, isolated for the first time the active principle of the peyote cactus, mescaline. It was the first time that an entheogenic alkaloid had been isolated from a natural botanical species. The following year, in 1898, he published his work in the academic journal Naunyn-Schmiedeberg's Archives of Pharmacology The active ingredient was called 'mescaline'.; because the alkaloid was extracted from the dried buttons known as 'mescal buttons'.
In 1919, based on Heffter's description of the molecular structure of mescaline, Ernst Späth, an Austrian chemist, synthesized the molecule for the first time in the Chemical Laboratory of the University of Vienna in Austria. It was the first time that a hallucinogenic alkaloid was synthesized in the laboratory.
In 1955, English politician Christopher Mayhew participated in an experiment for the BBC's Panorama program, in which he ingested 400 mg of mescaline under the supervision of psychiatrist Humphry Osmond. This event is known as The Mescaline Experiment of 1955. Although the recording was deemed too controversial and ultimately omitted from the series, Mayhew praised the experience, calling it "the most interesting thing I've ever done in my life".
Chemical Structure
Mescaline structurally consists of three methoxide groups attached to a benzene ring at positions 3,4, and 5, plus an aliphatic side chain with an amino group.
Chemical classification
Hallucinogens can be divided, structurally, into two classes: tryptamines and phenylethylamines (also called phenethylamines). Mescaline is the most significant representative of the phenylethylamines. Within the group of tryptamines are psilocybin and dimethyltryptamine.
Biosynthesis
In 1950 Reti proposed that mescaline could be biosynthesized by conversion of tyrosine to dihydroxyphenylalanine (dopa) followed by decarboxylation of dihydroxyphenethylamine (dopamine), hydroxylation to normescaline, and finally O-methylations to obtain mescaline.
Biochemical Effects
Mescaline inhibits the oxidation of sodium lactate, pyruvate, and glutamate in the subject's brain; however it has no effect on the oxidation of sodium succinate. On this basis sodium succinate has been used as an antidote in mescaline poisoning in humans.
Uses
Mescaline has been used for at least 5,700 years by native Americans. This makes it possibly the oldest alkaloid used by humans. The San Pedro cactus (T. pachanoi) is used to this day as part of northern curanderismo, especially in rituals from the northern table of the northern coast and highlands of Peru, and southern Ecuador. As of November 14, 2022, this tradition of use is Cultural Heritage of the Nation in Peru.
Other cacti
Although the most studied cactus that contains mescaline is Lophophora williamsii, there are others that also contain the alkaloid, such as those of the genus Trichocereus: T. bridgesii, T. macrogonus, T. scopulicola, T. terscheckii, T. werdermannianus and T. pachanoi. The latter is the most ethnographically important.
The mescaline molecule is a phenylethylamine, structurally related to the molecule of the neurotransmitter dopamine, which is another phenylethylamine, and not to serotonin, which is an indole (at the level of chemical structure they have nothing to do with it). Chemical synthesis of this molecule is possible, but is relatively expensive.
Cultural references
In literature
Some writers have explored altered states of consciousness from mescaline experimentation producing notable works of world literature:
- Artaud, Antonin (1948). Travel to the country of the Tarahumaras [chuckles]D'un voyage au pays des Tarahumaras] (in French). Paris: Fontaine, coll. "L'Âge d'or".
- Huxley, Aldous (1954). The gates of perception [chuckles]The Doors of Perception] (in English).
- Huxley, Aldous (1956). Heaven and hell [chuckles]Heaven and Hell] (in English).
- Michaux, Henri (1956). Miserable Miracle (Mescaline) [chuckles]Misérable miracle (La mescaline)] (in French).
- Pollan, Michael (2021). This Is Your Mind on Plants.
At the movies
Some filmmakers, from the genres of fiction, experimental and documentary, have explored in their films the altered states of consciousness caused by the ingestion of mescaline, be it through the alkaloid, the peyote cactus or the San Pedro cactus:
- Images du monde visionnaire (1964), Henri Michaux and Eric Duvivier (directors), (Switzerland, educational).
- Peyote Queen (1965), Storm de Hirsch (directora), (United States, experimental).
- Hikure-Tame. The pilgrimage of the peyote among the huicholes (1977), Nicolás Echevarría (director), (Mexico, documentary).
- Eduardo the healer (1978), Douglas Sharon (productor), (USA, documentary).
- Puerto Escondido (1992), Gabriele Salvatores (director), (Italy, fiction).
- Flowers in the Desert (2009), José Álvarez (director), (Mexico, documentary).
- Venado (2009), Pablo Fulgueira (director), (Mexico, documentary).
- Crystal Fairy (2012), Sebastián Silva (director), (Chile, fiction).
- How to Change Your Mind [chuckles]How to change your mind] (2022), Alex Gibney and Michael Pollan (producer), (documentary).