2C-x: Difference between revisions

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[[File:2C-x.svg|250px|thumbnail|The general structure for a 2C-x compound]]

'''2C-''x''''' is the general name for the family of ~~synthetic~~ [[phenethylamines]] originally studied by [[Alexander Shulgin]]. Shulgin first synthesized most of the 2C-''x'' chemicals in the 1970s and later published his findings in his book [[PiHKAL]]. The 2C-''x'' chemicals vary in effect from being totally inactive to fully psychedelic.

'''Substituted dimethoxyphenethylamines''' (also known as '''2C-''x''''') is the general name for the family of psychedelic [[phenethylamines]] originally studied by [[Alexander Shulgin]]. Shulgin first synthesized most of the 2C-''x'' chemicals in the 1970s and later published his findings in his book [[PiHKAL]]. He also coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group. The 2C-''x'' chemicals vary in effect from being totally inactive to fully [[psychedelic]]. Some of the most popular members of this group include [[2C-B]], [[2C-E]], and [[2C-I]].

==List of 2C-x compounds ==

==Chemistry==

All derivatives of [[2,5-dimethoxyphenethylamine]] have a [[phenethylamine]] backbone with two methoxy groups in positions 2 and 5 of the aromatic ring and they further contain different lipophilic substituents in position 4.

The phenethylamine backbone consists of a phenyl ring joined to an amine group through an ethyl chain. All compounds in the 2C-x series consist of this as their core structure.

==List of 2C-x compounds==

Note: This list does not include [[2C-T-x]], [[25x-NBOH]], [[25x-NBOMe]], [[DOx]].

===Classic 2C-x compounds===

{| class="wikitable"

|-

! scope="col" | '''Compound'''

! scope="col" |'''Compound'''

! scope="col" style="width: 50px;" | '''R4~~'''~~

! scope="col" style="width: 50px;" |'''R4'''

~~! scope="col" style="width: 50px;" | '''Rβ~~'''

! scope="col" |'''Structure'''

! scope="col" | '''Structure'''

|-

| [[2C-B]] ~~|| Br~~ || H || [[File:2C-B.svg|200px]]

|[[2C-H]]||H||[[File:2C-H.svg|200px]]

|-

| [[~~βk-~~2C-B]] || Br ~~|| =O~~ || [[File:~~Βk-~~2C-B.svg|200px]]

|[[2C-B]]||Br||[[File:2C-B.svg|200px]]

|-

| [[2C-C]] || Cl ~~|| H~~ || [[File:2C-C.svg|200px]]

|[[2C-C]]||Cl||[[File:2C-C.svg|200px]]

|-

| [[2C-D]] || CH3 ~~|| H~~ || [[File:2C-D.svg|200px]]

|[[2C-D]]||CH3||[[File:2C-D.svg|200px]]

|-

| [[2C-E]] || CH2CH3 ~~|| H~~ || [[File:2C-E.svg|200px]]

|[[2C-E]]||CH2CH3||[[File:2C-E.svg|200px]]

|-

| [[2C-H]] || ~~H || H~~ || [[File:2C-H.svg|200px]]

|[[2C-EF]]||CH2CFH2||[[File:2C-EF.svg|200px]]

|-

| [[2C-I]] || I ~~|| H~~ || [[File:2C-I.svg|200px]]

|[[2C-I]]||I||[[File:2C-I.svg|200px]]

|-

| 2C-iP || CH(CH3)2 ~~|| H~~ || [[File:2C-iP.svg|200px]]

|2C-iP||CH(CH3)2||[[File:2C-iP.svg|200px]]

|-

| [[2C-P]] || CH2CH2CH3 ~~|| H~~ || [[File:2C-P.svg|200px]]

|[[2C-P]]||CH2CH2CH3||[[File:2C-P.svg|200px]]

|-

| 2C-TFM || CF3 ~~|| H~~ || [[File:2C-TFM.svg|201px]]

|2C-TFM||CF3||[[File:2C-TFM.svg|201px]]

|-

| 2C-~~T || SCH3 || H || [[File:2C-T.svg~~|~~200px]]~~

|}

===Other compounds, derivated from 2,5-dimethoxyphenethylamine===

{| class="wikitable"

|-

| ~~[[2C-T-2]]~~ || ~~SCH~~2CH3 || ~~H || [[File:2C-T-2.svg|200px]]~~

! scope="col" |'''Compound'''

! scope="col" style="width: 50px;" |'''R3'''

! scope="col" style="width: 50px;" |'''R4'''

! scope="col" style="width: 50px;" |'''R6'''

! scope="col" style="width: 50px;" |'''Rβ'''

! scope="col" |'''Structure'''

|-

| ~~2C-T-4~~ || ~~SCH(~~CH3)2 ~~|| H~~ || [[File:~~2C-T-4~~.svg|200px]]

|[[BOD]]||H||CH3||H||OCH3||[[File:BOD.svg|200px]]

|-

| [[2C-~~T-7~~]] || ~~SCH2CH2CH3~~ || H || [[File:2C-~~T-7~~.svg|200px]]

|[[βk-2C-B]]||H||Br||H||=O||[[File:Βk-2C-B.svg|200px]]

|-

| [[2C-T-21]] || ~~SCH~~2CH2 || H || [[File:2C-T-21.svg|200px]]

|[[2C-B-FLY]]||CH2-||Br||CH2-||H||[[File:2C-B-FLY.svg|200px]]

|-

|}

==~~Health effects,~~ potential ~~addiction and tolerance~~==

==Toxicity and harm potential==

The 2C-x chemicals, as with many other serotonergic psychedelics, should not be taken in combination with SSRIs (selective [[serotonin]] [[reuptake ~~Inhibitor~~]]) or [[tricyclic antidepressants]] in general to avoid [[~~Serotonin Syndrome~~]], a potentially life-threatening condition in which an abundance of serotonin is built up the body, causing many physical and cognitive health problems.

The 2C-x chemicals, as with many other serotonergic psychedelics, should not be taken in combination with SSRIs (selective [[serotonin]] [[reuptake inhibitor]]) or [[tricyclic antidepressants]] in general to avoid [[serotonin syndrome]], a potentially life-threatening condition in which an abundance of serotonin is built up the body, causing many physical and cognitive health problems.

===Dangerous interactions===

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==Legal status==

*'''Austria:''' The 2C-x family is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich) or the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}

*'''USA:''' In the US, most of the 2C-x chemicals are Schedule I under the American Food and Drug Administration Safety and Innovation Act of 2012 and the Federal Analogue Act.<ref>http://www.justice.gov/ola/views-letters/112/093011-ltr-re-hr1254-synthetic-drug-control-act-2011.pdf</ref>

*'''Australia:''' Australia has a blanket ban over all substituted phenethylamines including the entire 2C-X family.<ref>New Psychoactive Substances (National Drug and Alcohol Research Centre 2014) | https://comorbidity.edu.au/sites/default/files/cre/page/New%20Psychoactive%20Substances.pdf</ref>

*'''Switzerland:''' Most 2C-x drugs are illegal to possess, produce and sell.<ref>http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html</ref>

*'''Switzerland:''' Most 2C-x drugs are illegal to possess, produce and sell.<ref>{{Citation | year=2017 | title=SR 812.121.11 Verordnung des EDI vom 30. Mai 2011 über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Betäubungsmittelverzeichnisverordnung, BetmVV-EDI) | url=http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html}}</ref>

*'''Canada:''' All 2C-x phenethylamines are schedule III in Canada. <ref>~~http~~://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-14.html~~#docCont~~</ref>

*'''Canada:''' All 2C-x phenethylamines are schedule III in Canada. <ref>{{Citation | title=Consolidated federal laws of Canada, Controlled Drugs and Substances Act | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-14.html}}</ref>

*'''United Kingdom:''' Most of the 2C-x chemical class are Class A drugs in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>~~United Kingdom. (1977).~~ Misuse of Drugs Act 1971 (~~S.I.~~ 1977~~/1243). London: The Stationery Office Limited. Retrieved July 5, 2017, from http~~://www.legislation.gov.uk/uksi/1977/1243/made</ref>

*'''United Kingdom:''' Most of the 2C-x chemical class are Class A drugs in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>{{Citation | title=The Misuse of Drugs Act 1971 (Modification) Order 1977 | url=https://www.legislation.gov.uk/uksi/1977/1243/made}}</ref>

*'''Germany:''' Most 2C-x compounds are controlled under BtMG Anlage I, making them illegal to manufacture, import, possess, sell, or transfer them without a license.<ref>https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html</ref> Other 2C-x compounds are controlled by the NpSG, as they are derivatives of 2-Phenethylamine. Production, and sale is illegal. Possession and import, although illegal, is not penalized if intended for self-consumption.<ref>https://www.gesetze-im-internet.de/npsg/anlage.html</ref>

*'''Germany:''' Most 2C-x compounds are controlled under BtMG Anlage I, making them illegal to manufacture, import, possess, sell, or transfer them without a license.<ref>{{Citation | title=Anlage I BtMG - Einzelnorm | url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html}}</ref> Other 2C-x compounds are controlled by the NpSG, as they are derivatives of 2-Phenethylamine. Production, and sale is illegal. Possession and import, although illegal, is not penalized if intended for self-consumption.<ref>{{Citation | title=Anlage NpSG - Einzelnorm | url=https://www.gesetze-im-internet.de/npsg/anlage.html}}</ref>

==See also==

*[[Responsible use]]

*[[DOx]]

*[[2C-T-x]]

*[[25x-NBOMe]]

*[[Psychedelics]]

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==External links==

*[https://en.wikipedia.org/wiki/2C_(psychedelics) 2C (Wikipedia)]

==Literature==

* Dean, B. V., Stellpflug, S. J., Burnett, A. M., & Engebretsen, K. M. (2013). 2C or not 2C: Phenethylamine Designer Drug Review. Journal of Medical Toxicology, 9(2), 172-178. https://doi.org/10.1007/s13181-013-0295-x

*Dean, B. V., Stellpflug, S. J., Burnett, A. M., & Engebretsen, K. M. (2013). 2C or not 2C: Phenethylamine Designer Drug Review. Journal of Medical Toxicology, 9(2), 172-178. https://doi.org/10.1007/s13181-013-0295-x

==References==

[[Category:Chemical class]]

[[Category:2C-x| ]]

@@ Line 1: / Line 1: @@
 [[File:2C-x.svg|250px|thumbnail|The general structure for a 2C-x compound]]
-'''2C-''x''''' is the general name for the family of synthetic [[phenethylamines]] originally studied by [[Alexander Shulgin]]. Shulgin first synthesized most of the 2C-''x'' chemicals in the 1970s and later published his findings in his book [[PiHKAL]]. The 2C-''x'' chemicals vary in effect from being totally inactive to fully psychedelic.
+'''Substituted dimethoxyphenethylamines''' (also known as '''2C-''x''''') is the general name for the family of psychedelic [[phenethylamines]] originally studied by [[Alexander Shulgin]]. Shulgin first synthesized most of the 2C-''x'' chemicals in the 1970s and later published his findings in his book [[PiHKAL]]. He also coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group. The 2C-''x'' chemicals vary in effect from being totally inactive to fully [[psychedelic]]. Some of the most popular members of this group include [[2C-B]], [[2C-E]], and [[2C-I]].
-==List of 2C-x compounds ==
+==Chemistry==
+{{chemistry}}
+All derivatives of [[2,5-dimethoxyphenethylamine]] have a [[phenethylamine]] backbone with two methoxy groups in positions 2 and 5 of the aromatic ring and they further contain different lipophilic substituents in position 4.
+The phenethylamine backbone consists of a phenyl ring joined to an amine group through an ethyl chain. All compounds in the 2C-x series consist of this as their core structure.
+==List of 2C-x compounds==
+Note: This list does not include [[2C-T-x]], [[25x-NBOH]], [[25x-NBOMe]], [[DOx]].
+===Classic 2C-x compounds===
 {| class="wikitable"
 |-
-! scope="col" | '''Compound'''
+! scope="col" |'''Compound'''
-! scope="col" style="width: 50px;" | '''R<sub>4</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>4</sub>'''
-! scope="col" style="width: 50px;" | '''R<sub>β</sub>'''
+! scope="col" |'''Structure'''
-! scope="col" | '''Structure'''
 |-
-| [[2C-B]] || Br || H || [[File:2C-B.svg|200px]]
+|[[2C-H]]||H||[[File:2C-H.svg|200px]]
 |-
-| [[βk-2C-B]] || Br || =O || [[File:Βk-2C-B.svg|200px]]
+|[[2C-B]]||Br||[[File:2C-B.svg|200px]]
 |-
-| [[2C-C]] || Cl || H || [[File:2C-C.svg|200px]]
+|[[2C-C]]||Cl||[[File:2C-C.svg|200px]]
 |-
-| [[2C-D]] || CH<sub>3</sub> || H || [[File:2C-D.svg|200px]]
+|[[2C-D]]||CH<sub>3</sub>||[[File:2C-D.svg|200px]]
 |-
-| [[2C-E]] || CH<sub>2</sub>CH<sub>3</sub> || H || [[File:2C-E.svg|200px]]
+|[[2C-E]]||CH<sub>2</sub>CH<sub>3</sub>||[[File:2C-E.svg|200px]]
 |-
-| [[2C-H]] || H || H || [[File:2C-H.svg|200px]]
+|[[2C-EF]]||CH<sub>2</sub>CFH<sub>2</sub>||[[File:2C-EF.svg|200px]]
 |-
-| [[2C-I]] || I || H || [[File:2C-I.svg|200px]]
+|[[2C-I]]||I||[[File:2C-I.svg|200px]]
 |-
-| 2C-iP || CH<sub></sub>(CH<sub>3</sub>)<sub>2</sub> || H || [[File:2C-iP.svg|200px]]
+|2C-iP||CH<sub></sub>(CH<sub>3</sub>)<sub>2</sub>||[[File:2C-iP.svg|200px]]
 |-
-| [[2C-P]] || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || H || [[File:2C-P.svg|200px]]
+|[[2C-P]]||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||[[File:2C-P.svg|200px]]
 |-
-| 2C-TFM || CF<sub>3</sub> || H || [[File:2C-TFM.svg|201px]]
+|2C-TFM||CF<sub>3</sub>||[[File:2C-TFM.svg|201px]]
 |-
-| 2C-T<!-- general structure for a 2C-T-x compound --> || SCH<sub>3</sub> || H || [[File:2C-T.svg|200px]]
+|}
+===Other compounds, derivated from 2,5-dimethoxyphenethylamine===
+{| class="wikitable"
 |-
-| [[2C-T-2]] || SCH<sub>2</sub>CH<sub>3</sub> || H || [[File:2C-T-2.svg|200px]]
+! scope="col" |'''Compound'''
+! scope="col" style="width: 50px;" |'''R<sub>3</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>4</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>6</sub>'''
+! scope="col" style="width: 50px;" |'''R<sub>β</sub>'''
+! scope="col" |'''Structure'''
 |-
-| 2C-T-4 || SCH(CH<sub>3</sub>)<sub>2</sub> || H || [[File:2C-T-4.svg|200px]]
+|[[BOD]]||H||CH<sub>3</sub>||H||OCH<sub>3</sub>||[[File:BOD.svg|200px]]
 |-
-| [[2C-T-7]] || SCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || H || [[File:2C-T-7.svg|200px]]
+|[[βk-2C-B]]||H||Br||H||=O||[[File:Βk-2C-B.svg|200px]]
 |-
-| [[2C-T-21]] || SCH<sub>2</sub>CH<sub>2</sub> || H || [[File:2C-T-21.svg|200px]]
+|[[2C-B-FLY]]||CH<sub>2</sub>-||Br||CH<sub>2</sub>-||H||[[File:2C-B-FLY.svg|200px]]
 |-
 |}
-==Health effects, potential addiction and tolerance==
+==Toxicity and harm potential==
-The 2C-x chemicals, as with many other serotonergic psychedelics, should not be taken in combination with SSRIs (selective [[serotonin]] [[reuptake Inhibitor]]) or [[tricyclic antidepressants]] in general to avoid [[Serotonin Syndrome]], a potentially life-threatening condition in which an abundance of serotonin is built up the body, causing many physical and cognitive health problems.
+{{toxicity}}
+The 2C-x chemicals, as with many other serotonergic psychedelics, should not be taken in combination with SSRIs (selective [[serotonin]] [[reuptake inhibitor]]) or [[tricyclic antidepressants]] in general to avoid [[serotonin syndrome]], a potentially life-threatening condition in which an abundance of serotonin is built up the body, causing many physical and cognitive health problems.
 ===Dangerous interactions===
@@ Line 50: / Line 65: @@
 ==Legal status==
 *'''Austria:''' The 2C-x family is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich) or the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}
 *'''USA:''' In the US, most of the 2C-x chemicals are Schedule I under the American Food and Drug Administration Safety and Innovation Act of 2012 and the Federal Analogue Act.<ref>http://www.justice.gov/ola/views-letters/112/093011-ltr-re-hr1254-synthetic-drug-control-act-2011.pdf</ref>
 *'''Australia:''' Australia has a blanket ban over all substituted phenethylamines including the entire 2C-X family.<ref>New Psychoactive Substances (National Drug and Alcohol Research Centre 2014) | https://comorbidity.edu.au/sites/default/files/cre/page/New%20Psychoactive%20Substances.pdf</ref>
-*'''Switzerland:''' Most 2C-x drugs are illegal to possess, produce and sell.<ref>http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html</ref>
+*'''Switzerland:''' Most 2C-x drugs are illegal to possess, produce and sell.<ref>{{Citation | year=2017 | title=SR 812.121.11 Verordnung des EDI vom 30. Mai 2011 über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Betäubungsmittelverzeichnisverordnung, BetmVV-EDI) | url=http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html}}</ref>
-*'''Canada:''' All 2C-x phenethylamines are schedule III in Canada. <ref>http://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-14.html#docCont</ref>
+*'''Canada:''' All 2C-x phenethylamines are schedule III in Canada. <ref>{{Citation | title=Consolidated federal laws of Canada, Controlled Drugs and Substances Act | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/page-14.html}}</ref>
-*'''United Kingdom:''' Most of the 2C-x chemical class are Class A drugs in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>United Kingdom. (1977). Misuse of Drugs Act 1971 (S.I. 1977/1243). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/1977/1243/made</ref>
+*'''United Kingdom:''' Most of the 2C-x chemical class are Class A drugs in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>{{Citation | title=The Misuse of Drugs Act 1971 (Modification) Order 1977 | url=https://www.legislation.gov.uk/uksi/1977/1243/made}}</ref>
-*'''Germany:''' Most 2C-x compounds are controlled under BtMG Anlage I, making them illegal to manufacture, import, possess, sell, or transfer them without a license.<ref>https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html</ref> Other 2C-x compounds are controlled by the NpSG, as they are derivatives of 2-Phenethylamine. Production, and sale is illegal. Possession and import, although illegal, is not penalized if intended for self-consumption.<ref>https://www.gesetze-im-internet.de/npsg/anlage.html</ref>
+*'''Germany:''' Most 2C-x compounds are controlled under BtMG Anlage I, making them illegal to manufacture, import, possess, sell, or transfer them without a license.<ref>{{Citation | title=Anlage I BtMG - Einzelnorm | url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html}}</ref> Other 2C-x compounds are controlled by the NpSG, as they are derivatives of 2-Phenethylamine. Production, and sale is illegal. Possession and import, although illegal, is not penalized if intended for self-consumption.<ref>{{Citation | title=Anlage NpSG - Einzelnorm | url=https://www.gesetze-im-internet.de/npsg/anlage.html}}</ref>
 ==See also==
 *[[Responsible use]]
 *[[DOx]]
+*[[2C-T-x]]
 *[[25x-NBOMe]]
 *[[Psychedelics]]
@@ Line 66: / Line 84: @@
 ==External links==
 *[https://en.wikipedia.org/wiki/2C_(psychedelics) 2C (Wikipedia)]
 ==Literature==
-* Dean, B. V., Stellpflug, S. J., Burnett, A. M., & Engebretsen, K. M. (2013). 2C or not 2C: Phenethylamine Designer Drug Review. Journal of Medical Toxicology, 9(2), 172-178. https://doi.org/10.1007/s13181-013-0295-x
+*Dean, B. V., Stellpflug, S. J., Burnett, A. M., & Engebretsen, K. M. (2013). 2C or not 2C: Phenethylamine Designer Drug Review. Journal of Medical Toxicology, 9(2), 172-178. https://doi.org/10.1007/s13181-013-0295-x
 ==References==
 <references />
+[[Category:Chemical class]]
+[[Category:2C-x| ]]