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-B-Chemdraw.png 2C-B-3d-sticks.png
2C-Bn H CH2C6H5 2C-Bn structure.png
2C-Bu H CH2CH2CH2CH3 2C-Bu structure.png
2C-C H Cl 2C-C.svg 2C-C-3d-sticks.png
2C-C-3 [4] Cl Cl 2CC3 structure.png
2C-CN H C≡N 2C-CN structure.png
2C-CP H C3H5 2C-cP structure.png
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-EF structure.png
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-1 CH2 2C-G-1.png
2C-G-2 (CH2)2 2C-G-2.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-G-5 (CH2)5 2C-G-5.svg
2C-G-6 (CH2)6 2C-G-6.png
2C-G-N (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-iP H CH(CH3)2 2C-iP structure.png
2C-N H NO2 2C-N-Chemdraw.png 2C-N-3d-sticks.png
2C-NH2 H NH2 2C-NH2 structure.png
2C-PYR H Pyrrolidine 2C-PYR structure.png
2C-PIP H Piperidine 2C-PIP structure.png
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-MOM [5] H CH2OCH3 2C-MOM structure.png
2C-P H CH2CH2CH3 2C-P-Chemdraw.png 2C-P-3d-sticks.png
2C-Ph H C6H5 2C-Ph structure.png
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-3[6] 2CT3 structure.png
2C-T-4 H SCH(CH3)2 2C-T-4-Chemdraw.png 2C-T-4-3d-sticks.png
2C-T-5[6] 2CT5 structure.png
2C-T-6[6] 2CT6 structure.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[6] 2CT9 structure.png
2C-T-10[6] 2CT10 structure.png
2C-T-11[6] 2CT11 structure.png
2C-T-12[6] 2CT12 structure.png
2C-T-13 H S(CH2)2OCH3 2C-T-13-Chemdraw.png 2C-T-13-3d-sticks.png
2C-T-14[7] 2CT14 structure.png
2C-T-15 H SCH(CH2)2 2C-T-15-Chemdraw.png 2C-T-15-3d-sticks.png
2C-T-16 [8] 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-18[7] 2CT18 structure.png
2C-T-19 H SCH2CH2CH2CH3 2C-T-9-Chemdraw.png 2C-T-19-3d-sticks.png
2C-T-21 H S(CH2)2F 2C-T-21-Chemdraw.png 2C-T-21-3d-sticks.png
2C-T-21.5[7] 2CT21.5 structure.png
2C-T-22[7] 2CT22 structure.png
2C-T-23[7] 2CT23 structure.png
2C-T-24[7] 2CT24 structure.png
2C-T-25[7] 2CT25 structure.png
2C-T-27[7] 2CT27 structure.png
2C-T-28[7] 2CT28 structure.png
2C-T-30[7] 2CT30 structure.png
2C-T-31[7] 2CT31 structure.png
2C-T-32[7] 2CT32 structure.png
2C-T-33[7] 2CT33 structure.png
2C-DFM [9]:770 H CHF2 2C-DFM structure.png
2C-TFM H CF3 2C-TFM-Chemdraw.png 2C-TFM-3d.png
2C-TFE H CH2CF3 2C-TFE structure.png
2C-YN H C≡CH 2C-YN skeletal.svg
2C-V H CH=CH2 2C-V structure.png
2C-AL H CH2CH=CH2 2C-AL structure.png

Legality[edit]

Canada[edit]

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

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. ^ 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. ^ a b c d e f g "Shulgin's Sulfur Symphony – Part I". countyourculture. 15 January 2011.
  7. ^ a b c d e f g h i j k l m "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.