2C (psychedelics)

2C (2C-x) is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring.

[4] Most of the currently known 2C compounds were first synthesized by Alexander Shulgin in the 1970s and 1980s and published in his book PiHKAL (Phenethylamines i Have Known And Loved).

[3] Shulgin also coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group.

[6][8][10] Unlike many other phenethylamines, 2C drugs, including 2C-C, 2C-D, 2C-E, 2C-I, and 2C-T-2 among others, are inactive as monoamine releasing agents and reuptake inhibitors.

[6][8] In contrast to most psychedelics, at least two assessed 2C drugs, 2C-C and 2C-P, have shown refinorcing effects in rodents, including conditioned place preference (CPP) and self-administration.

[6][15][16][17][18][19][20] Similarly to DOI, tolerance has been found to gradually develop to the head-twitch response induced by 2C-T-7 with chronic administration in rodents.

[5][32][23][1][27] 2C-B gained popularity as a recreational drug and MDMA alternative in the mid-1980s and became a controlled substance in the United States in 1994.

[3] As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substance (Schedule III) in Canada.