Category:Phenethylamines: Difference between revisions

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The breadth is striking: the body's own signalling molecules: dopamine,

noradrenaline, and adrenaline are phenethylamines; so are the stimulants

amphetamine and methamphetamine; so is the empathogen MDMA; so are the

[[Amphetamine|amphetamine]] and [[Methamphetamine|methamphetamine]]; so is the empathogen [[MDMA]]; so are the

[[:Category:Psychostimulants|psychostimulant]] cathinones; and so are a number

of ordinary medicines, among them some decongestants and bronchodilators. This

page concerns one particular branch of that family: the '''psychedelic

phenethylamines''', the serotonergic, vision-producing members, of which the

oldest and most famous is mescaline.<ref name="mescaline-revival">Vamvakopoulou IA, Narine KAD. Mescaline: The forgotten psychedelic. ''Neuropharmacology''. 2023 Jan 1;222:109294. PMID: 36252614.</ref> Their history, like that of the

oldest and most famous is [[Mescaline|mescaline]].<ref name="mescaline-revival">Vamvakopoulou IA, Narine KAD. Mescaline: The forgotten psychedelic. ''Neuropharmacology''. 2023 Jan 1;222:109294. PMID: 36252614.</ref> Their history, like that of the

[[:Category:Tryptamines|tryptamine psychedelics]], is best told as a history of

people, and it begins with a cactus.

== Peyote and the first psychedelic ==

Mescaline is the active principle of '''peyote''' (''Lophophora williamsii''),

[[Mescaline]] is the active principle of '''[[Peyote|peyote]]''' (''Lophophora williamsii''),

a small, spineless cactus of the deserts of northern Mexico and the southern

United States, and of related cacti including the San Pedro. Peyote is among

United States, and of related cacti including the San Pedro. [[Peyote]] is among

the most anciently used psychoactive plants known: dried peyote buttons

the most anciently used psychoactive plants known: dried [[Peyote|peyote]] buttons

recovered from caves in Texas and Mexico have been dated to several thousand

years before the present, and it has been used ceremonially and medicinally by

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That long tradition was met, after the Spanish conquest, with sustained

persecution. The Catholic Church treated the divinatory use of peyote as

persecution. The Catholic Church treated the divinatory use of [[Peyote|peyote]] as

evidence of a pact with the devil, and the Inquisition condemned it; peyote

evidence of a pact with the devil, and the Inquisition condemned it; [[Peyote|peyote]]

ceremonies survived chiefly among peoples such as the Huichol, the Cora, and

the Tarahumara, who could retreat into terrain remote enough to escape the

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Not every voice of the period was condemnatory. As early as 1591 the physician

Juan de Cárdenas argued that peyote's effects were a matter of its natural

Juan de Cárdenas argued that [[Peyote|peyote]]'s effects were a matter of its natural

properties, not of the supernatural, a strikingly early statement of what

would now be called a pharmacological view.

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}}

In the nineteenth century peyote drew the attention of Western science. The

In the nineteenth century [[Peyote|peyote]] drew the attention of Western science. The

German toxicologist Louis Lewin examined the cactus in the 1880s, and in 1897

the chemist '''Arthur Heffter''', working in Leipzig, isolated its principal

active alkaloid and, by a series of self-experiments, identified it as the

substance responsible for peyote's visions. He named it '''mescaline'''. In

substance responsible for [[Peyote|peyote]]'s visions. He named it '''[[Mescaline|mescaline]]'''. In

1919 the Viennese chemist '''Ernst Späth''' achieved the first complete

synthesis of mescaline, making it the first psychedelic substance both

synthesis of [[Mescaline|mescaline]], making it the first psychedelic substance both

identified and made in the laboratory.<ref name="psychedelic-history">Nichols DE, Nichols CD. History of psychedelic drug science and molecular pharmacology. ''International Review of Neurobiology''. 2025. PMID: 40541313.</ref> Mescaline became, for the first half of

identified and made in the laboratory.<ref name="psychedelic-history">Nichols DE, Nichols CD. History of psychedelic drug science and molecular pharmacology. ''International Review of Neurobiology''. 2025. PMID: 40541313.</ref> [[Mescaline]] became, for the first half of

the twentieth century, the standard tool for the scientific study of

visionary states, and its literary fame was secured when Aldous Huxley

described his own mescaline experience in ''The Doors of Perception'' in 1954.<ref name="huxley1954">Huxley A. ''The Doors of Perception''. London: Chatto & Windus; 1954.</ref>

described his own [[Mescaline|mescaline]] experience in ''The Doors of Perception'' in 1954.<ref name="huxley1954">Huxley A. ''The Doors of Perception''. London: Chatto & Windus; 1954.</ref>

{{PendellsCorner

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The modern history of the psychedelic phenethylamines is, to an unusual degree,

the work of one person: the chemist '''Dr. Alexander "Sasha" Shulgin'''.

Beginning in the 1960s, Shulgin took the mescaline molecule as a template and

Beginning in the 1960s, Shulgin took the [[Mescaline|mescaline]] molecule as a template and

systematically varied it, synthesizing and then personally evaluating, first

on himself, then with his wife Ann and a small circle of friends, a great

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== Prohibition and revival ==

As with the other classical psychedelics, the psychedelic phenethylamines were

brought under strict legal control: mescaline was placed in the most

brought under strict legal control: [[Mescaline|mescaline]] was placed in the most

restrictive category of control in the United States by the early 1970s, with

a narrow exemption for the religious use of peyote by the Native American

a narrow exemption for the religious use of [[Peyote|peyote]] by the Native American

Church, and the later synthetic phenethylamines were controlled as they

appeared. Research nonetheless continued at a low level and has revived in

recent years, with renewed scientific and commercial interest in mescaline and

recent years, with renewed scientific and commercial interest in [[Mescaline|mescaline]] and

related substances as possible treatments in psychiatry;<ref name="mescaline-revival" /> as of the mid-2020s

this work is at an early stage and these remain investigational rather than

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== Members ==

The psychedelic phenethylamines fall into several groups. At the head of the

family stands '''mescaline''', the naturally occurring member. The largest

family stands '''[[Mescaline|mescaline]]''', the naturally occurring member. The largest

synthetic groups are the [[:Category:2C-x series|2C-x series]], covered as a

class on its own page, and the DOx series, the latter being the

amphetamine-type relatives, longer-acting and more potent. A further group, the

[[Amphetamine|amphetamine]]-type relatives, longer-acting and more potent. A further group, the

'''NBOMe series''', consists of N-benzyl derivatives of the 2C compounds; these

are far more potent than their parents and, as noted below, considerably more

dangerous. The list is not exhaustive, and the boundaries of the family are

drawn differently by different authorities. The broader, non-psychedelic

phenethylamines, the amphetamine-type stimulants, MDMA and the other

phenethylamines, the [[Amphetamine|amphetamine]]-type stimulants, [[MDMA]] and the other

empathogens, the cathinones, are treated under their own categories.

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substances act at the 5-HT2A receptor is well established; how that receptor

activity gives rise to the actual psychedelic experience is far less well

understood and remains a subject of active research. The amphetamine-type

understood and remains a subject of active research. The [[Amphetamine|amphetamine]]-type

members, such as the DOx compounds, also carry the structural features of a

stimulant, which contributes to their long duration and their effects on the

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== Safety ==

The psychedelic phenethylamines do not all carry the same risks, and the

differences between them matter a great deal. Mescaline itself, used in the

differences between them matter a great deal. [[Mescaline]] itself, used in the

forms in which it has the longest record, has a low potential for the kind of

physical dependence associated with substances such as opioids; its

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[[Category:MedCategory]]

[[Category:MedCategoryFull]]

[[Category:Pharmaceutical]]

[[Category:Plants]]

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