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.[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-Bn H CH2C6H5
2C-Bu H CH2CH2CH2CH3
2C-C H Cl
2C-CN H C≡N
2C-CP H C3H5
2C-D H CH3
2C-E H CH2CH3
2C-EF H CH2CH2F
2C-F H F
2C-G CH3 CH3
2C-G-3 (CH2)3
2C-G-4 (CH2)4
2C-NPH (CH)4
2C-H H H
2C-I H I
2C-N H NO2
2C-NH2 H NH2
2C-O H OCH3
2C-O-4 H OCH(CH3)2
2C-P H CH2CH2CH3
2C-iP H CH(CH3)2
2C-Ph H C6H5
2C-SE H Se CH3
2C-T H SCH3
2C-T-2 H SCH2CH3
2C-T-4 H SCH(CH3)2
2C-T-7 H S(CH2)2CH3
2C-T-8 H SCH2CH(CH2)2
2C-T-9 H SC(CH3)3
2C-T-13 H S(CH2)2OCH3
2C-T-15 H SCH(CH2)2
2C-T-16 H SCH2CH=CH2
2C-T-17 H SCH(CH3)CH2CH3
2C-T-21 H S(CH2)2F
2C-TFM H CF3
2C-TFE H CH2CF3
2C-YN H C≡CH
2C-V H CH=CH2

Legality

Canada

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

See also

References

  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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