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 coined 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-C-3 [4] Cl 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-1 CH2
2C-G-2 (CH2)2
2C-G-3 (CH2)3
2C-G-4 (CH2)4
2C-G-5 (CH2)5
2C-G-6 (CH2)6
2C-G-N (CH)4
2C-H H H
2C-I H I
2C-iP H CH(CH3)2
2C-N H NO2
2C-NH2 H NH2
2C-PYR H Pyrrolidine
2C-PIP H Piperidine
2C-O H OCH3
2C-O-4 H OCH(CH3)2
2C-MOM [5] H CH2OCH3
2C-P H CH2CH2CH3
2C-Ph H C6H5
2C-Se H Se CH3
2C-T H SCH3
2C-T-2 H SCH2CH3
2C-T-3[6]
2C-T-4 H SCH(CH3)2
2C-T-5[6]
2C-T-6[6]
2C-T-7 H S(CH2)2CH3
2C-T-8 H SCH2CH(CH2)2
2C-T-9[6]
2C-T-10[6]
2C-T-11[6]
2C-T-12[6]
2C-T-13 H S(CH2)2OCH3
2C-T-14[7]
2C-T-15 H SCH(CH2)2
2C-T-16 [8] H SCH2CH=CH2
2C-T-17 H SCH(CH3)CH2CH3
2C-T-18[7]
2C-T-19 H SCH2CH2CH2CH3
2C-T-21 H S(CH2)2F
2C-T-21.5[7]
2C-T-22[7]
2C-T-23[7]
2C-T-24[7]
2C-T-25[7]
2C-T-27[7]
2C-T-28[7]
2C-T-30[7]
2C-T-31[7]
2C-T-32[7]
2C-T-33[7]
2C-DFM [9]:770 H CHF2
2C-TFM H CF3
2C-TFE H CH2CF3
2C-YN H C≡CH
2C-V H CH=CH2
2C-AL H CH2CH=CH2

Legality

Canada

As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substances (Schedule III) in Canada.[10]

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. Takahashi M, Nagashima M, Suzuki J, Seto T, Yasuda I, Yoshida T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77(4): 1245–1272. doi:10.1016/j.talanta.2008.07.062
  5. Leth-Petersen S, Petersen IN, Jensen AA, Bundgaard C, Bæk M, Kehler J, Kristensen JL. 5-HT2A/5-HT2C receptor pharmacology and intrinsic clearance of N-benzylphenethylamines modified at the primary site of metabolism. ACS Chem. Neurosci., 16 Nov 2016, 7 (11), 1614–1619. doi:10.1021/acschemneuro.6b00265
  6. "Shulgin's Sulfur Symphony – Part I". countyourculture. 15 January 2011.
  7. "Shulgin's Sulfur Symphony – Part I". countyourculture. 15 January 2011.
  8. Daniel Trachsel (2003). "Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines)". Helvetica Chimica Acta. 86 (7): 2610–2619. doi:10.1002/hlca.200390210.
  9. Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  10. "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. April 15, 2016. Retrieved August 28, 2016.
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