2C (psychedelics)

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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.[1] Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting compounds.[2] 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). Shulgin also invented the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group.[3]

General structure of a 2C compound
Nomenclature R3 R4 2D Structure 3D Structure
2C-B H Br 2C-B-Chemdraw.png 2C-B-3d-sticks.png
2C-Bn H CH2C6H5
2C-Bu H CH2CH2CH2CH3
2C-C H Cl 2C-C.svg 2C-C-3d-sticks.png
2C-CN H C≡N
2C-CP H C3H5
2C-D H CH3 2C-D-Chemdraw.png 2C-D-3d-sticks.png
2C-E H CH2CH3 2C-E-Chemdraw.png 2C-E-3d-sticks.png
2C-EF H CH2CH2F
2C-F H F 2C-F-Chemdraw.png 2C-F-3d-sticks.png
2C-G CH3 CH3 2C-G-Chemdraw.png 2C-G-3d-sticks.png
2C-G-3 (CH2)3 2C-G-3-Chemdraw.png 2C-G-3-3d.png
2C-G-4 (CH2)4 2C-G-4-Chemdraw.png 2C-G-4-3d2.png
2C-NPH (CH)4 2C-G-N-Chemdraw.png 2C-G-N-3d.png
2C-H H H 2C-H-Chemdraw.png 2C-H-3d-sticks.png
2C-I H I 2C-I-Chemdraw.png 2C-I-3d-sticks.png
2C-N H NO2 2C-N-Chemdraw.png 2C-N-3d-sticks.png
2C-NH2 H NH2
2C-O H OCH3 2C-O-Chemdraw.png 2C-O-3d.png
2C-O-4 H OCH(CH3)2 2C-O-4-Chemdraw.png 2C-O-4-3d.png
2C-P H CH2CH2CH3 2C-P-Chemdraw.png 2C-P-3d-sticks.png
2C-iP H CH(CH3)2 2C-iP structure.png
2C-Ph H C6H5
2C-SE H Se CH3 2C-SE-Chemdraw.png 2C-SE-3d-sticks.png
2C-T H SCH3 2C-T-Chemdraw.png 2C-T-3d.png
2C-T-2 H SCH2CH3 2C-T-2-Chemdraw.png 2C-T-2-3d.png
2C-T-4 H SCH(CH3)2 2C-T-4-Chemdraw.png 2C-T-4-3d-sticks.png
2C-T-7 H S(CH2)2CH3 2C-T-7-Chemdraw.png 2C-T-7-3d-sticks.png
2C-T-8 H SCH2CH(CH2)2 2C-T-8-Chemdraw.png 2C-T-8-3d-sticks.png
2C-T-9 H SC(CH3)3 2C-T-9-Chemdraw.png 2C-T-19-3d-sticks.png
2C-T-13 H S(CH2)2OCH3 2C-T-13-Chemdraw.png 2C-T-13-3d-sticks.png
2C-T-15 H SCH(CH2)2 2C-T-15-Chemdraw.png 2C-T-15-3d-sticks.png
2C-T-16 H SCH2CH=CH2 2CT16 structure.png
2C-T-17 H SCH(CH3)CH2CH3 2C-T-17-Chemdraw.png 2C-T-17-3d-sticks.png
2C-T-21 H S(CH2)2F 2C-T-21-Chemdraw.png 2C-T-21-3d-sticks.png
2C-TFM H CF3 2C-TFM-Chemdraw.png 2C-TFM-3d.png
2C-TFE H CH2CF3
2C-YN H C≡CH 2C-YN skeletal.svg
2C-V H CH=CH2

Legality[edit]

Canada[edit]

As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substance (Schedule III) in Canada.[4]

See also[edit]

References[edit]

  1. ^ Alexander Shulgin, Tania Manning and Paul F Daley. The Shulgin Index. Volume 1. Psychedelic Phenethylamines and Related Compounds. Transform Press, 2011. ISBN 978-0-9630096-3-0
  2. ^ Daniel Trachsel, David Lehmann and Christoph Enzensperger. Phenethylamine Von der Struktur zur Funktion, pp 762-810. Nachtschatten Verlag AG, 2013. ISBN 978-3-03788-700-4
  3. ^ Shulgin, Alexander; Ann Shulgin (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 
  4. ^ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. April 15, 2016. Retrieved August 28, 2016. 
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