Category:2C-x series

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.^[1] 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 story of the 2C-x compounds begins with mescaline. Mescaline is the principal psychoactive alkaloid of the peyote cactus, isolated and identified in the 1890s and established by self-experiment as the source of the cactus's visionary effects. For the first half of the twentieth century it was the best-known psychedelic of Western science, and through Aldous Huxley's 1954 book The Doors of Perception it reached a wide public.

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.^[2]

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.^[3] 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.^[4]

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.^[3] 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.

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.^[5] 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 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 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.