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
General structure of a 2C compound
Nomenclature R3 R4 2D Structure CAS number
2C-B H Br
2C-B-Chemdraw.png
66142-81-2
2C-Bn H CH2C6H5
2C-Bn structure.png
2C-Bu H CH2CH2CH2CH3
2C-Bu structure.png
2C-C H Cl
2C-C.svg
88441-14-9
2C-C-3 [4] Cl Cl
2CC3 structure.png
2C-CN H C≡N
2C-CN structure.png
88441-07-0
2C-CP H C3H5
2C-cP structure.png
2C-D H CH3
2C-D-Chemdraw.png
24333-19-5
2C-E H CH2CH3
2C-E-Chemdraw.png
71539-34-9
2C-EF H CH2CH2F
2C-EF.svg
1222814-77-8
2C-F H F
2C-F-Chemdraw.png
207740-15-6
2C-G CH3 CH3
2C-G-Chemdraw.png
207740-18-9
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
207740-19-0
2C-G-4 (CH2)4
2C-G-4-Chemdraw.png
952006-59-6
2C-G-5 (CH2)5
2C-G-5.svg
207740-20-3
2C-G-6 (CH2)6
2C-G-6.png
2C-G-N (CH)4
2C-G-N-Chemdraw.png
207740-21-4
2C-H H H
2C-H-Chemdraw.png
3600-86-0
2C-I H I
2C-I-Chemdraw.png
69587-11-7
2C-iP H CH(CH3)2
2C-iP structure.png
1498978-47-4
2C-N H NO2
2C-N-Chemdraw.png
261789-00-8
2C-NH2 H NH2
2C-NH2 structure.png
168699-66-9
2C-PYR H Pyrrolidine
2C-PYR structure.png
2C-PIP H Piperidine
2C-PIP structure.png
2C-O H OCH3
2C-O-Chemdraw.png
15394-83-9
2C-O-4 H OCH(CH3)2
2C-O-4-Chemdraw.png
952006-65-4
2C-MOM [5] H CH2OCH3
2C-MOM structure.png
2C-P H CH2CH2CH3
2C-P-Chemdraw.png
207740-22-5
2C-Ph H C6H5
2C-Ph structure.png
2C-Se H Se CH3
2C-SE-Chemdraw.png
1189246-68-1
2C-T H SCH3
2C-T-Chemdraw.png
61638-09-3
2C-T-2 H SCH2CH3
2C-T-2-Chemdraw.png
207740-24-7
2C-T-3[6] H SCH2C(=CH2)CH3
2C-T-3.svg
648957-40-8
2C-T-4 H SCH(CH3)2
2C-T-4-Chemdraw.png
207740-25-8
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
207740-26-9
2C-T-8 H SCH2CH(CH2)2
2C-T-8-Chemdraw.png
207740-27-0
2C-T-9[6]
2CT9 structure.png
207740-28-1
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.svg
207740-30-5
2C-T-14[6]
2CT14 structure.png
2C-T-15 H SCH(CH2)2
2C-T-15-Chemdraw.png
2C-T-16[7] H SCH2CH=CH2
2CT16 structure.png
648957-42-0
2C-T-17 H SCH(CH3)CH2CH3
2C-T-17-Chemdraw.png
207740-32-7
2C-T-18[6]
2CT18 structure.png
2C-T-19 H SCH2CH2CH2CH3
2C-T-9-Chemdraw.png
2C-T-21 H S(CH2)2F
2C-T-21-Chemdraw.png
207740-33-8
2C-T-21.5[6]
2CT21.5 structure.png
648957-46-4
2C-T-22[6]
2CT22 structure.png
648957-48-6
2C-T-23[6]
2CT23 structure.png
2C-T-24[6]
2CT24 structure.png
2C-T-25[6]
2CT25 structure.png
2C-T-27[6]
2CT27 structure.png
648957-52-2
2C-T-28[6]
2CT28 structure.png
648957-54-4
2C-T-30[6]
2CT30 structure.png
2C-T-31[6]
2CT31 structure.png
2C-T-32[6]
2CT32 structure.png
2C-T-33[6]
2CT33 structure.png
2C-DFM [8]: 770  H CHF2
2C-DFM structure.png
2C-TFM H CF3
2C-TFM-Chemdraw.png
159277-08-4
2C-TFE H CH2CF3
2C-TFE structure.png
2C-YN H C≡CH
2C-YN skeletal.svg
752982-24-4
2C-V H CH=CH2
2C-V structure.png
2C-AL H CH2CH=CH2
2C-AL structure.png

Legality

Canada

As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substance (Schedule III) in Canada.[9]

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; Shulgin, Ann (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 h i j k l m n o p q r s t "Shulgin's Sulfur Symphony – Part I". countyourculture. 15 January 2011. Archived from the original on 19 September 2019. Retrieved 22 October 2017.
  7. ^ 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.
  8. ^ Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  9. ^ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. April 15, 2016. Retrieved August 28, 2016.