View source for Chemistry:2C (psychedelics)

{{Short description|Family of phenethylamine psychedelics}}
'''2C''' ('''2C-''x''''') is a general name for the family of [[Chemistry:Psychedelic drug|psychedelic]] [[Biology:Phenethylamine|phenethylamine]]s containing methoxy groups on the 2 and 5 [[Chemistry:Carbon|positions]] of a [[Chemistry:Benzene|benzene]] ring.<ref>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}}</ref> Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more [[Biology:Metabolism|metabolically]] stable and longer acting compounds.<ref>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}}</ref> Most of the currently known 2C compounds were first synthesized by Alexander Shulgin in the 1970s and 1980s and published in his book ''[[Chemistry:PiHKAL|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.<ref>{{CitePiHKAL}}</ref>

[[File:2C-general.png|thumb|175px|right|General [[Chemistry:Skeletal formula|structure]] of a 2C compound]]

{| class="wikitable" style="background: #FFFFFF"
|-
! Nomenclature
!style="width:10em"| R3
!style="width:10em"| R4
! 2D Structure
! CAS number
|-
| [[Chemistry:2C-B|2C-B]]
| [[Chemistry:Hydrogen|H]]
| [[Chemistry:Bromine|Br]]
| [[File:2C-B-Chemdraw.png|115px]]
| 66142-81-2
|-
| 2C-Bn
| H
| CH<sub>2</sub>C<sub>6</sub>H<sub>5</sub>
| [[File:2C-Bn structure.png|115px]]
|
|-
| 2C-Bu
| H
| CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>
| [[File:2C-Bu structure.png|115px]]
|
|-
| [[Chemistry:2C-C|2C-C]]
| H
| [[Chemistry:Chlorine|Cl]]
| [[File:2C-C.svg|115px]]
| 88441-14-9
|-
| 2C-C-3 <ref>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}}</ref>
| [[Chemistry:Chlorine|Cl]]
| Cl
| [[File:2CC3 structure.png|115px]]
|
|-
| 2C-CN
| H
| C≡N
| [[File:2C-CN structure.png|115px]]
| 88441-07-0
|-
| [[Chemistry:2C-CP|2C-CP]]
| H
| [[Chemistry:Cyclopropane|C<sub>3</sub>H<sub>5</sub>]]
| [[File:2C-cP.svg|115px]]
|
|-
| [[Chemistry:2C-D|2C-D]]
| H
| [[Chemistry:Methyl group|CH<sub>3</sub>]]
| [[File:2C-D-Chemdraw.png|115px]]
| 24333-19-5
|-
| [[Chemistry:2C-E|2C-E]]
| H
| [[Chemistry:Ethyl group|CH<sub>2</sub>CH<sub>3</sub>]]
| [[File:2C-E-Chemdraw.png|115px]]
| 71539-34-9
|-
| [[Chemistry:2C-EF|2C-EF]]
| H
| CH<sub>2</sub>CH<sub>2</sub>F
| [[File:2C-EF.svg|115px]]
| 1222814-77-8
|-
| [[Chemistry:2C-F|2C-F]]
| H
| [[Chemistry:Fluorine|F]]
| [[File:2C-F-Chemdraw.png|115px]]
| 207740-15-6
|-
| [[Chemistry:2C-G|2C-G]]
| CH<sub>3</sub>
| CH<sub>3</sub>
| [[File:2C-G-Chemdraw.png|115px]]
| 207740-18-9
|-
| 2C-G-1
| colspan=2 | CH<sub>2</sub>
| [[File:2C-G-1.png|80px]]
|
|-
| 2C-G-2
| colspan=2 | (CH<sub>2</sub>)<sub>2</sub>
| [[File:2C-G-2.png|80px]]
|
|-
| 2C-G-3
| colspan=2 | (CH<sub>2</sub>)<sub>3</sub>
| [[File:2C-G-3-Chemdraw.png|115px]]
| 207740-19-0
|-
| 2C-G-4
| colspan=2 | (CH<sub>2</sub>)<sub>4</sub>
| [[File:2C-G-4-Chemdraw.png|115px]]
| 952006-59-6
|-
| 2C-G-5
| colspan=2 | (CH<sub>2</sub>)<sub>5</sub>
| [[File:2C-G-5.svg|80px]]
| 207740-20-3
|-
| 2C-G-6
| colspan=2 | (CH<sub>2</sub>)<sub>6</sub>
| [[File:2C-G-6.png|80px]]
|
|-
| 2C-G-N
| colspan=2 | (CH)<sub>4</sub>
| [[File:2C-G-N-Chemdraw.png|115px]]
| 207740-21-4
|-
| 2C-H
| H
| H
| [[File:2C-H-Chemdraw.png|115px]]
| 3600-86-0
|-
| [[Chemistry:2C-I|2C-I]]
| H
| [[Chemistry:Iodine|I]]
| [[File:2C-I-Chemdraw.png|115px]]
| 69587-11-7
|-
| [[Chemistry:2C-iP|2C-iP]]
| H
| CH(CH<sub>3</sub>)<sub>2</sub>
| [[File:2C-iP structure.png|115px]]
| 1498978-47-4
|-
| [[Chemistry:2C-N|2C-N]]
| H
| [[Chemistry:Nitro compound|NO<sub>2</sub>]]
| [[File:2C-N-Chemdraw.png|115px]]
| 261789-00-8
|-
| 2C-NH2
| H
| NH<sub>2</sub>
| [[File:2C-NH2 structure.png|115px]]
| 168699-66-9
|-
| 2C-PYR
| H
| [[Chemistry:Pyrrolidine|Pyrrolidine]]
| [[File:2C-PYR structure.png|115px]]
|
|-
| 2C-PIP
| H
| [[Chemistry:Piperidine|Piperidine]]
| [[File:2C-PIP structure.png|115px]]
|
|-
| 2C-O
| H
| OCH<sub>3</sub>
| [[File:2C-O-Chemdraw.png|115px]]
| 15394-83-9
|-
| [[Chemistry:2C-O-4|2C-O-4]]
| H
| [[Chemistry:Alkoxy group|OCH(CH<sub>3</sub>)<sub>2</sub>]]
| [[File:2C-O-4-Chemdraw.png|115px]]
| 952006-65-4
|-
| 2C-MOM <ref>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}}</ref>
| H
| [[Chemistry:Alkoxy group|CH<sub>2</sub>OCH<sub>3</sub>]]
| [[File:2C-MOM structure.png|115px]]
|
|-
| [[Chemistry:2C-P|2C-P]]
| H
| CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>
| [[File:2C-P-Chemdraw.png|115px]]
| 207740-22-5
|-
| 2C-Ph
| H
| C<sub>6</sub>H<sub>5</sub>
| [[File:2C-Ph structure.png|115px]]
|
|-
| [[Chemistry:2C-Se|2C-Se]]
| H
| [[Chemistry:Selenium|Se]] CH<sub>3</sub>
| [[File:2C-SE-Chemdraw.png|115px]]
| 1189246-68-1
|-
| [[Chemistry:2C-T|2C-T]]
| H
| [[Chemistry:Thioether|SCH<sub>3</sub>]]
| [[File:2C-T-Chemdraw.png|115px]]
| 61638-09-3
|-
| [[Chemistry:2C-T-2|2C-T-2]]
| H
| SCH<sub>2</sub>CH<sub>3</sub>
| [[File:2C-T-2-Chemdraw.png|115px]]
| 207740-24-7
|-
| [[Chemistry:2C-T-3|2C-T-3]]<ref name="Shulgin's Sulfur Symphony - Part II">{{cite web|title=Shulgin's Sulfur Symphony – Part I|url=http://countyourculture.com/2011/01/15/shulgins-sulfur-symphony-part-i/|website=countyourculture|date=15 January 2011|access-date=22 October 2017|archive-url=https://web.archive.org/web/20190919063901/http://countyourculture.com/2011/01/15/shulgins-sulfur-symphony-part-i/|archive-date=19 September 2019|url-status=dead}}</ref>
| H
| SCH<sub>2</sub>C(=CH<sub>2</sub>)CH<sub>3</sub>
| [[File:2C-T-3.svg|115px]]
|  648957-40-8
|-
| [[Chemistry:2C-T-4|2C-T-4]]
| H
| SCH(CH<sub>3</sub>)<sub>2</sub>
| [[File:2C-T-4-Chemdraw.png|115px]]
| 207740-25-8
|-
| 2C-T-5<ref name="Shulgin's Sulfur Symphony - Part II"/>
|
|
| [[File:2CT5 structure.png|115px]]
|
|-
| 2C-T-6<ref name="Shulgin's Sulfur Symphony - Part II"/>
|
|
| [[File:2CT6 structure.png|115px]]
|
|-
| [[Chemistry:2C-T-7|2C-T-7]]
| H
| S(CH<sub>2</sub>)<sub>2</sub>CH<sub>3</sub>
| [[File:2C-T-7-Chemdraw.png|115px]]
| 207740-26-9
|-
| [[Chemistry:2C-T-8|2C-T-8]]
| H
| SCH<sub>2</sub>CH(CH<sub>2</sub>)<sub>2</sub>
| [[File:2C-T-8-Chemdraw.png|115px]]
| 207740-27-0
|-
| 2C-T-9<ref name="Shulgin's Sulfur Symphony - Part II"/>
|
|
| [[File:2CT9 structure.png|115px]]
| 207740-28-1
|-
| 2C-T-10<ref name="Shulgin's Sulfur Symphony - Part II"/>
|
|
| [[File:2CT10 structure.png|115px]]
|
|-
| 2C-T-11<ref name="Shulgin's Sulfur Symphony - Part II"/>
|
|
| [[File:2CT11 structure.png|115px]]
|
|-
| 2C-T-12<ref name="Shulgin's Sulfur Symphony - Part II"/>
|
|
| [[File:2CT12 structure.png|115px]]
|
|-
| [[Chemistry:2C-T-13|2C-T-13]]
| H
| S(CH<sub>2</sub>)<sub>2</sub>OCH<sub>3</sub>
| [[File:2C-T-13.svg|115px]]
| 207740-30-5
|-
| 2C-T-14<ref name="Shulgin's Sulfur Symphony - Part II"/>
|
|
| [[File:2CT14 structure.png|115px]]
|
|-
| [[Chemistry:2C-T-15|2C-T-15]]
| H
| SCH(CH<sub>2</sub>)<sub>2</sub>
| [[File:2C-T-15-Chemdraw.png|115px]]
|
|-
| [[Chemistry:2C-T-16|2C-T-16]]<ref>{{cite journal |author=Daniel Trachsel |year=2003 |title=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) |journal=[[Chemistry:Helvetica Chimica Acta|Helvetica Chimica Acta]] |volume=86 |issue=7 |pages=2610–2619 |doi=10.1002/hlca.200390210}}</ref>
| H
| SCH<sub>2</sub>CH=CH<sub>2</sub>
| [[File:2CT16 structure.png|120px]]
|  648957-42-0
|-
| [[Chemistry:2C-T-17|2C-T-17]]
| H
| SCH(CH<sub>3</sub>)CH<sub>2</sub>CH<sub>3</sub>
| [[File:2C-T-17-Chemdraw.png|115px]]
| 207740-32-7
|-
| 2C-T-18<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT18 structure.png|115px]]
|
|-
| [[Chemistry:2C-T-19|2C-T-19]]
| H
| SCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>
| [[File:2C-T-9-Chemdraw.png|115px]]
|
|-
| [[Chemistry:2C-T-21|2C-T-21]]
| H
| S(CH<sub>2</sub>)<sub>2</sub>F
| [[File:2C-T-21-Chemdraw.png|115px]]
| 207740-33-8
|-
| 2C-T-21.5<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT21.5 structure.png|115px]]
|  648957-46-4
|-
| 2C-T-22<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT22 structure.png|115px]]
|  648957-48-6
|-
| 2C-T-23<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT23 structure.png|115px]]
|
|-
| 2C-T-24<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT24 structure.png|115px]]
|
|-
| 2C-T-25<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT25 structure.png|115px]]
|
|-
| 2C-T-27<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT27 structure.png|115px]]
| 648957-52-2
|-
| [[Chemistry:2C-T-28|2C-T-28]]<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT28 structure.png|115px]]
|  648957-54-4
|-
| 2C-T-30<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT30 structure.png|115px]]
|
|-
| 2C-T-31<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT31 structure.png|115px]]
|
|-
| 2C-T-32<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT32 structure.png|115px]]
|
|-
| 2C-T-33<ref name="Shulgin's Sulfur Symphony - Part II" />
|
|
| [[File:2CT33 structure.png|115px]]
|
|-
| 2C-DFM <ref name="Trachsel">{{cite book |author=Daniel Trachsel |author2=David Lehmann |author3=Christoph Enzensperger |name-list-style=amp |year=2013 |title=Phenethylamine: Von der Struktur zur Funktion |publisher=Nachtschatten Verlag AG |isbn=978-3-03788-700-4}}</ref>{{rp|770}}
| H
| CHF<sub>2</sub>
| [[File:2C-DFM structure.png|115px]]
|
|-
| [[Chemistry:2C-TFM|2C-TFM]]
| H
| [[Chemistry:Trifluoromethyl|CF<sub>3</sub>]]
| [[File:2C-TFM-Chemdraw.png|115px]]
| 159277-08-4
|-
| [[Chemistry:2C-TFE|2C-TFE]]
| H
| CH<sub>2</sub>CF<sub>3</sub>
| [[File:2C-TFE structure.png|115px]]
|
|-
| 2C-PFE
| H
| CF<sub>2</sub>CF<sub>3</sub>
| [[File:2C-PFE structure.png|115px]]
|
|-
| 2C-PFS
| H
| SF<sub>5</sub>
| [[File:2C-PFS structure.png|115px]]
|
|-
| [[Chemistry:2C-YN|2C-YN]]
| H
| [[Chemistry:Ethynyl|C≡CH]]
| [[File:2C-YN skeletal.svg|115px]]
| 752982-24-4
|-
| [[Chemistry:2C-V|2C-V]]
| H
| [[Chemistry:Vinyl group|CH=CH<sub>2</sub>]]
| [[File:2C-V structure.png|115px]]
|
|-
| [[Chemistry:2C-AL|2C-AL]]<ref>[https://patentscope.wipo.int/search/docs2/pct/WO2022006186/pdf/y_SatokAWjdK--I8ZkJqIVK_Vfz0IETYFMzHZaWlwlu_MA-hS0Wj-9jxUAfgWkQkRy3Rs2NUQ4ZdivqrrDDSaxeMxMgjwmy0MNVSgLhLhgAssl2gRNnZYIXdeBT9Cbko?docId=id00000063934462&filename=WO2022006186-PAMPH-20220106-4462.pdf Kruegel AC. Phenalkylamines and Methods of Treating Mood Disorders. Patent WO 2022/006186]</ref>
| H
| [[Chemistry:Allyl group|CH<sub>2</sub>CH=CH<sub>2</sub>]]
| [[File:2C-AL structure.png|115px]]
|
|}

==Legality==

===Canada===
As of October 12, 2016, the 2C-''x'' family of substituted phenethylamines is a controlled substance (Schedule III) in Canada.<ref>{{Cite web |title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) |url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php |work=Canada Gazette |volume=150 |issue=9 |date=April 15, 2016 |access-date=August 28, 2016}}</ref>

==See also==
* [[Chemistry:25-NB|25-NB]]
* [[Chemistry:Substituted phenethylamine|Substituted phenethylamine]]s
* [[Chemistry:Substituted amphetamine|Substituted amphetamine]]s
* Substituted methylenedioxyphenethylamines
* [[Chemistry:DOx|DOx]]
* [[Chemistry:Substituted tryptamine|Substituted tryptamine]]s
* [[Chemistry:List of miscellaneous 5HT2A agonists|List of miscellaneous 5HT2A agonists]]

== References ==
{{Reflist}}

{{2C's}}
{{Hallucinogens}}
{{Serotonergics}}
{{TAAR ligands}}
{{Phenethylamines}}

{{DEFAULTSORT:2c (Psychedelics)}}
[[Category:Phenethylamines]]

{{Sourceattribution|2C (psychedelics)}}