Category:2C-x series: Difference between revisions

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The 2C-x series is a family of synthetic psychedelic phenethylamines — chemical relatives of [[mescaline]], the psychedelic compound of the peyote cactus. Almost the entire family is the work of a single chemist, Dr. Alexander 'Sasha' Shulgin, who made the compounds by systematically modifying the mescaline molecule one position at a time, then swallowed his creations, always dosing from minuscule to effect, then sharing the ones he liked with his wife, and the ones they both liked with their friends, and on it went.<ref name="pihkal">Shulgin AT, Shulgin AS. ''PiHKAL: A Chemical Love Story.'' Berkeley: Transform Press; 1991.</ref> The "2C" in the name is Shulgin's own shorthand, marking the two carbon atoms between the molecule's benzene ring and its amino group.

The 2C-x series is a family of synthetic psychedelic phenethylamines, chemical relatives of [[mescaline]], the psychedelic compound of the peyote cactus. Almost the entire family is the work of a single chemist, Dr. Alexander 'Sasha' Shulgin, who made the compounds by systematically modifying the mescaline molecule one position at a time, then swallowed his creations, always dosing from minuscule to effect, then sharing the ones he liked with his wife, and the ones they both liked with their friends, and on it went.<ref name="pihkal">Shulgin AT, Shulgin AS. ''PiHKAL: A Chemical Love Story.'' Berkeley: Transform Press; 1991.</ref> The "2C" in the name is Shulgin's own shorthand, marking the two carbon atoms between the molecule's benzene ring and its amino group.

== Mescaline, and a chemist's project ==

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Mescaline is a phenethylamine — a small molecule built on a benzene ring joined to an amino group by a two-carbon chain. From the 1960s onward Dr. Alexander 'Sasha' Shulgin took the mescaline molecule as a starting point and began, methodically, to alter it: changing the chemical groups attached to the ring, and testing what each change did. The good Dr. Shulgin worked first at the Dow Chemical Company and then, from the mid-1960s, in a private laboratory at his home in California; over several decades he synthesized and personally tested more than two hundred compounds, recording the results in the 1991 book ''PiHKAL'' ("Phenethylamines I Have Known and Loved"), written with his wife Ann Shulgin.<ref name="cen">Alexander T. (Sasha) Shulgin. ''Chem Eng News.'' 2014;92(33). https://cen.acs.org/articles/92/i33/Alexander-T-Sasha-Shulgin.html</ref>

Mescaline is a phenethylamine, a small molecule built on a benzene ring joined to an amino group by a two-carbon chain. From the 1960s onward Dr. Alexander 'Sasha' Shulgin took the mescaline molecule as a starting point and began, methodically, to alter it: changing the chemical groups attached to the ring, and testing what each change did. The good Dr. Shulgin worked first at the Dow Chemical Company and then, from the mid-1960s, in a private laboratory at his home in California; over several decades he synthesized and personally tested more than two hundred compounds, recording the results in the 1991 book ''PiHKAL'' ("Phenethylamines I Have Known and Loved"), written with his wife Ann Shulgin.<ref name="cen">Alexander T. (Sasha) Shulgin. ''Chem Eng News.'' 2014;92(33). https://cen.acs.org/articles/92/i33/Alexander-T-Sasha-Shulgin.html</ref>

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== The 2C-x compounds ==

The 2C-x compounds are the members of this family in which the two-carbon chain carries no extra methyl group — distinguishing them from the related "DOx" series, which Dr. Shulgin also explored. The best known is [[2C-B]], synthesized by Dr. Shulgin in 1974 and described by him in the scientific literature in 1975.<ref name="2cb">2C-B. Wikipedia.</ref> Others include [[2C-E]], [[2C-I]], [[2C-D]], [[2C-P]], [[2C-C]], and the sulfur-containing "2C-T" sub-group, among them [[2C-T-2]] and [[2C-T-7]]. Several members — [[2C-B]], [[2C-E]], [[2C-T-2]], and [[2C-T-7]] — were singled out by Shulgin, alongside [[mescaline]] and one DOx compound, as a personal "magical half-dozen" of the phenethylamines he considered most significant.<ref name="psy2cb">2C-B. PsychonautWiki.</ref>

The 2C-x compounds are the members of this family in which the two-carbon chain carries no extra methyl group, distinguishing them from the related "DOx" series, which Dr. Shulgin also explored. The best known is [[2C-B]], synthesized by Dr. Shulgin in 1974 and described by him in the scientific literature in 1975.<ref name="2cb">2C-B. Wikipedia.</ref> Others include [[2C-E]], [[2C-I]], [[2C-D]], [[2C-P]], [[2C-C]], and the sulfur-containing "2C-T" sub-group, among them [[2C-T-2]] and [[2C-T-7]]. Several members, [[2C-B]], [[2C-E]], [[2C-T-2]], and [[2C-T-7]], were singled out by Shulgin, alongside [[mescaline]] and one DOx compound, as a personal "magical half-dozen" of the phenethylamines he considered most significant.<ref name="psy2cb">2C-B. PsychonautWiki.</ref>

In the 1970s [[2C-B]] saw limited use as an aid to psychotherapy by a small number of practitioners in the United States, who valued its relatively short duration and mild character.<ref name="2cb"/> From the mid-1980s it also appeared as a recreational substance, sold briefly and legally under names such as "Nexus" before it was brought under control.

== Research chemicals and legal control ==

The publication of ''PiHKAL'' placed full synthesis methods for the 2C-x compounds in the public domain, and from the 1990s onward several members appeared on the market as "research chemicals" — compounds sold, often online, in a space outside both medical use and existing drug law. [[2C-B]] was placed in the most restrictive United States drug schedule in the mid-1990s; [[2C-T-7]] was placed under emergency Schedule I control in the United States on September 20, 2002 and permanently scheduled on March 18, 2004, following reports of deaths associated with its use.<ref name="2ct7">2C-T-7. Wikipedia.</ref> In 1999 the United Kingdom moved to bring the compounds described in ''PiHKAL'' under its drug law as a class. Many further 2C-x compounds have since been controlled in many countries, in some cases through general provisions written to cover whole chemical families at once.

The publication of ''PiHKAL'' placed full synthesis methods for the 2C-x compounds in the public domain, and from the 1990s onward several members appeared on the market as "research chemicals", compounds sold, often online, in a space outside both medical use and existing drug law. [[2C-B]] was placed in the most restrictive United States drug schedule in the mid-1990s; [[2C-T-7]] was placed under emergency Schedule I control in the United States on September 20, 2002 and permanently scheduled on March 18, 2004, following reports of deaths associated with its use.<ref name="2ct7">2C-T-7. Wikipedia.</ref> In 1999 the United Kingdom moved to bring the compounds described in ''PiHKAL'' under its drug law as a class. Many further 2C-x compounds have since been controlled in many countries, in some cases through general provisions written to cover whole chemical families at once.

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== Mechanisms ==

The 2C-x compounds are understood to act, like other classical psychedelics, as agonists at serotonin receptors, with activity at the 5-HT2A receptor thought to be central to their psychedelic effects. The precise relationship between this receptor activity and the subjective effects is not fully established. The compounds vary widely in potency, in the dose required, and in the duration of their effects, and the structure-activity relationships across the family — how a given change to the molecule changes its effect — were a principal subject of Dr. Shulgin's work. That these compounds bind and activate serotonin receptors is well established; the fuller relationship between that action and the range of their effects remains a subject of research.

The 2C-x compounds are understood to act, like other classical psychedelics, as agonists at serotonin receptors, with activity at the 5-HT2A receptor thought to be central to their psychedelic effects. The precise relationship between this receptor activity and the subjective effects is not fully established. The compounds vary widely in potency, in the dose required, and in the duration of their effects, and the structure-activity relationships across the family, how a given change to the molecule changes its effect, were a principal subject of Dr. Shulgin's work. That these compounds bind and activate serotonin receptors is well established; the fuller relationship between that action and the range of their effects remains a subject of research.

== Safety ==

The 2C-x compounds vary greatly in potency and in the dose at which they are active, and several are noted for being unpredictable and strongly dose-sensitive — a small increase in dose can produce a disproportionate increase in effect. Reported adverse effects include intense and sometimes distressing psychological experiences, nausea and other gastrointestinal effects, and, with some members at higher doses, a difficult physical "body load". Some 2C-x compounds have been associated with serious harm and with deaths, [[2C-T-7]] notably among them. As serotonergic compounds, they are generally considered inadvisable to combine with other serotonergic drugs, including the SSRIs and MAOI antidepressants, because of the risk of serotonin toxicity. The compounds are also commonly sold without reliable knowledge of identity or dose, which is itself a substantial source of risk. Figures for these risks are uncertain, and individual response varies considerably between people.

The 2C-x compounds vary greatly in potency and in the dose at which they are active, and several are noted for being unpredictable and strongly dose-sensitive, a small increase in dose can produce a disproportionate increase in effect. Reported adverse effects include intense and sometimes distressing psychological experiences, nausea and other gastrointestinal effects, and, with some members at higher doses, a difficult physical "body load". Some 2C-x compounds have been associated with serious harm and with deaths, [[2C-T-7]] notably among them. As serotonergic compounds, they are generally considered inadvisable to combine with other serotonergic drugs, including the SSRIs and MAOI antidepressants, because of the risk of serotonin toxicity. The compounds are also commonly sold without reliable knowledge of identity or dose, which is itself a substantial source of risk. Figures for these risks are uncertain, and individual response varies considerably between people.

== References ==

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