2C (psychedelics)

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File:2C-general.png
General structure of a 2C compound

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]

Nomenclature R3 R4 2D Structure CAS number
2C-B H Br File:2C-B.svg 66142-81-2
2C-Bn H CH2C6H5 File:2C-Bn structure.png
2C-Bu H CH2CH2CH2CH3 File:2C-Bu structure.png
2C-C H Cl File:2C-C.svg 88441-14-9
2C-C-3 [4] Cl Cl File:2CC3 structure.png
2C-CN H C≡N File:2C-CN structure.png 88441-07-0
2C-D H CH3 File:2C-D-Chemdraw.png 24333-19-5
2C-E H CH2CH3 File:2C-E-Chemdraw.png 71539-34-9
2C-EF H CH2CH2F File:2C-EF.svg 1222814-77-8
2C-F H F File:2C-F-Chemdraw.png 207740-15-6
2C-G CH3 CH3 File:2C-G-Chemdraw.png 207740-18-9
2C-G-1 CH2 File:2C-G-1.png
2C-G-2 (CH2)2 File:2C-G-2.png
2C-G-3 (CH2)3 File:2C-G-3-Chemdraw.png 207740-19-0
2C-G-4 (CH2)4 File:2C-G-4-Chemdraw.png 952006-59-6
2C-G-5 (CH2)5 File:2C-G-5.svg 207740-20-3
2C-G-6 (CH2)6 File:2C-G-6.png
2C-G-N (CH)4 File:2C-G-N-Chemdraw.png 207740-21-4
2C-H H H File:2C-H-Chemdraw.png 3600-86-0
2C-I H I File:2C-I-Chemdraw.png 69587-11-7
2C-iP H CH(CH3)2 File:2C-iP structure.png 1498978-47-4
2C-TBU H C(CH3)3 File:2C-TBU structure.png
2C-CP H C3H5 File:2C-cP.svg 2888537-46-8
2C-CPE H C5H9 File:2C-CPE structure.png
2C-N H NO2 File:2C-N-Chemdraw.png 261789-00-8
2C-NH2 H NH2 File:2C-NH2 structure.png 168699-66-9
2C-PYR H Pyrrolidine File:2C-PYR structure.png
2C-PIP H Piperidine File:2C-PIP structure.png
2C-O H OCH3 File:2C-O-Chemdraw.png 15394-83-9
2C-O-4 H OCH(CH3)2 File:2C-O-4-Chemdraw.png 952006-65-4
2C-MOM [5] H CH2OCH3 File:2C-MOM structure.png
2C-P H CH2CH2CH3 File:2C-P2DACS.svg 207740-22-5
2C-Ph H C6H5 File:2C-Ph structure.png
2C-Se H Se CH3 File:2C-SE-Chemdraw.png 1189246-68-1
2C-T H SCH3 File:2C-T-Chemdraw.png 61638-09-3
2C-T-2 H SCH2CH3 File:2C-T-2-Chemdraw.png 207740-24-7
2C-T-3[6] H SCH2C(=CH2)CH3 File:2C-T-3.svg 648957-40-8
2C-T-4 H SCH(CH3)2 File:2C-T-4-Chemdraw.png 207740-25-8
2C-T-5[6] File:2CT5 structure.png
2C-T-6[6] File:2CT6 structure.png
2C-T-7 H S(CH2)2CH3 File:2C-T-7-Chemdraw.png 207740-26-9
2C-T-8 H SCH2CH(CH2)2 File:2C-T-8-Chemdraw.png 207740-27-0
2C-T-9[6] File:2CT9 structure.png 207740-28-1
2C-T-10[6] File:2CT10 structure.png
2C-T-11[6] File:2CT11 structure.png
2C-T-12[6] File:2CT12 structure.png
2C-T-13 H S(CH2)2OCH3 File:2C-T-13.svg 207740-30-5
2C-T-14[6] File:2CT14 structure.png
2C-T-15 H SCH(CH2)2 File:2C-T-15-Chemdraw.png
2C-T-16[7] H SCH2CH=CH2 File:2CT16 structure.png 648957-42-0
2C-T-17 H SCH(CH3)CH2CH3 File:2C-T-17-Chemdraw.png 207740-32-7
2C-T-18[6] File:2CT18 structure.png
2C-T-19 H SCH2CH2CH2CH3 File:2C-T-9-Chemdraw.png
2C-T-21 H S(CH2)2F File:2C-T-21-Chemdraw.png 207740-33-8
2C-T-21.5[6] File:2CT21.5 structure.png 648957-46-4
2C-T-22[6] File:2CT22 structure.png 648957-48-6
2C-T-23[6] File:2CT23 structure.png
2C-T-24[6] File:2CT24 structure.png
2C-T-25[6] File:2CT25 structure.png
2C-T-27[6] File:2CT27 structure.png 648957-52-2
2C-T-28[6] File:2CT28 structure.png 648957-54-4
2C-T-30[6] File:2CT30 structure.png
2C-T-31[6] File:2CT31 structure.png
2C-T-32[6] File:2CT32 structure.png
2C-T-33[6] File:2CT33 structure.png
2C-T-DFM H SCF2H File:2C-T-DFM structure.png
CYB210010[8] H SCF3 File:CYB210010 structure.png
2C-T-DFP H SCH2CH2CF2H File:2C-T-DFP structure.png
2C-T-PARGY H SCH2C≡CH File:2C-T-PARGY structure.png
2C-DFM [9]: 770  H CHF2 File:2C-DFM structure.png
2C-TFM H CF3 File:2C-TFM-Chemdraw.png 159277-08-4
2C-TFE H CH2CF3 File:2C-TFE structure.png
2C-PFE H CF2CF3 File:2C-PFE structure.png
2C-PFS H SF5 File:2C-PFS structure.png
2C-YN H C≡CH File:2C-YN skeletal.svg 752982-24-4
2C-V H CH=CH2 File:2C-V structure.png
2C-AL[10] H CH2CH=CH2 File: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.[11]

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. ↑ 6.00 6.01 6.02 6.03 6.04 6.05 6.06 6.07 6.08 6.09 6.10 6.11 6.12 6.13 6.14 6.15 6.16 6.17 6.18 6.19 "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. ↑ Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, Morgan ME, Reichelt AC, Pathare P, Stang E, Palfreyman MG, Nivorozhkin A. Synthesis and Structure-Activity Relationships of 2,5-Dimethoxy-4-Substituted Phenethylamines and the Discovery of CYB210010: A Potent, Orally Bioavailable and Long-Acting Serotonin 5-HT2 Receptor Agonist. J Med Chem. 2024 Apr 25;67(8):6144-6188. doi:10.1021/acs.jmedchem.3c01961 PMID 38593423
  9. ↑ Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
  10. ↑ Kruegel AC. Phenalkylamines and Methods of Treating Mood Disorders. Patent WO 2022/006186
  11. ↑ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. April 15, 2016. Retrieved August 28, 2016.
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