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2C-C: Difference between revisions
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{{SubstanceBox/2C-C}} | {{SubstanceBox/2C-C}} | ||
'''4-Chloro-2,5-dimethoxyphenethylamine''' (commonly known as '''2C-C''') is a lesser-known [[Psychoactive class::psychedelic]] substance of the [[Chemical class::phenethylamine]] class that produces [[psychedelic]] effects when [[routes of administration|administered]].<ref>Alexander Shulgin - | '''4-Chloro-2,5-dimethoxyphenethylamine''' (commonly known as '''2C-C''') is a lesser-known [[Psychoactive class::psychedelic]] substance of the [[Chemical class::phenethylamine]] class that produces [[psychedelic]] effects when [[routes of administration|administered]].<ref name="PiHKAL">{{cite book|title=PiHKAL: A Chemical Love Story|title-link=PiHKAL|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|chapter-url=https://erowid.org/library/books_online/pihkal/pihkal022.shtml|chapter=#22. 2C-C}}</ref> It is a member of the [[2C-x family]] of psychedelic phenethylamines, all of which were derived from the systematic modification of the [[mescaline]] molecule. | ||
2C-C was first synthesized by Alice C. Cheng and Neal Castagnoli Jr. in 1983 as an intermediate in a study evaluating the neurotoxicity of 6-hydroxydopamine analogs.<ref>Cheng | 2C-C was first synthesized by Alice C. Cheng and Neal Castagnoli Jr. in 1983 as an intermediate in a study evaluating the neurotoxicity of 6-hydroxydopamine analogs.<ref>{{cite journal|last1=Cheng|first1=A. C.|last2=Castagnoli Jr|first2=N.|year=1984|title=Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2, 5-dihydroxyphenyl)-2-aminoethane analogs of 6-hydroxydopamine|journal=Journal of Medicinal Chemistry|volume=27|issue=4|pages=513-520|doi=10.1021/jm00370a014|pmid=6423824|issn=0022-2623|eissn=1520-4804|oclc=39480771}}</ref> Its activity in humans was later investigated and documented by [[Alexander Shulgin]] in his book [[PiHKAL]] ("Phenethylamines I Have Known and Loved"). | ||
Many users report that the effects of 2C-C are gentler, more relaxed, and [[Sedation|sedating]] than other closely related [[psychedelic]] [[phenethylamines]] such as [[2C-B]], [[2C-I]], and [[2C-E]]. It is one of the least potent members of the 2C-x family, with muted visual effects and a relatively unaltered headspace. | Many users report that the effects of 2C-C are gentler, more relaxed, and [[Sedation|sedating]] than other closely related [[psychedelic]] [[phenethylamines]] such as [[2C-B]], [[2C-I]], and [[2C-E]]. It is one of the least potent members of the 2C-x family, with muted visual effects and a relatively unaltered headspace. | ||
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==Chemistry== | ==Chemistry== | ||
[[File:Phenethylamine.png|thumb|right|253px|thumb|right | [[File:Phenethylamine.png|thumb|right|253px|thumb|right||Generic structure of a phenethylamine molecule]] | ||
2C-C or 2,5-dimethoxy-4-chlorophenethylamine is a substituted [[phenethylamines|phenethylamine]] featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain. 2C-C contains methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as a chlorine atom attached to carbon R<sub>4</sub> of the phenyl ring. 2C-C belongs to the 2C family of phenethylamines which contain methoxy groups on the 2 and 5 positions of the benzene ring.<ref name=" | 2C-C or 2,5-dimethoxy-4-chlorophenethylamine is a substituted [[phenethylamines|phenethylamine]] featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain. 2C-C contains methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as a chlorine atom attached to carbon R<sub>4</sub> of the phenyl ring. 2C-C belongs to the 2C family of phenethylamines which contain methoxy groups on the 2 and 5 positions of the benzene ring.<ref name="PiHKAL" /> | ||
==Pharmacology== | ==Pharmacology== | ||
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|{{effects/physical| | |{{effects/physical| | ||
*'''[[Effect::Stimulation]]''' & '''[[Effect::Sedation]]''' - In terms of its effects on the physical energy levels of the user, the 2C-C experience typically begins with mild stimulation, but usually becomes somewhat sedating as the experience progresses and surprisingly lacks the distinctive energetic feeling associated with most [[phenethylamines]]. This is described in [[PiHKAL]] as "''an intense form of relaxation.''"<ref name=" | *'''[[Effect::Stimulation]]''' & '''[[Effect::Sedation]]''' - In terms of its effects on the physical energy levels of the user, the 2C-C experience typically begins with mild stimulation, but usually becomes somewhat sedating as the experience progresses and surprisingly lacks the distinctive energetic feeling associated with most [[phenethylamines]]. This is described in [[PiHKAL]] as "''an intense form of relaxation.''"<ref name="PiHKAL"/> | ||
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of 2C-C can be described as a pleasurable, warm, soft, all-encompassing and mild tingling sensation. This maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached. | *'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of 2C-C can be described as a pleasurable, warm, soft, all-encompassing and mild tingling sensation. This maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached. | ||
*'''[[Effect::Bodily control enhancement]]''' - Whilst at lower doses one may find that their bodily control is enhanced, at higher dosages this becomes suppressed. | *'''[[Effect::Bodily control enhancement]]''' - Whilst at lower doses one may find that their bodily control is enhanced, at higher dosages this becomes suppressed. | ||
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}} | }} | ||
===Combinational effects=== | ===Combinational effects=== | ||
*'''[[Cannabis]]''' - Cannabis majorly intensifies and extends both the sensory and cognitive effects of 2C-C. Extreme caution should be exercised with this combination as it can also elevate the [[anxiety]], [[confusion]] and [[psychosis]] risk of cannabis. | *'''[[Cannabis]]''' - Cannabis majorly intensifies and extends both the sensory and cognitive effects of 2C-C. Extreme caution should be exercised with this combination as it can also elevate the [[anxiety]], [[confusion]] and [[psychosis]] risk of cannabis. | ||
*'''[[Dissociatives]]''' - When combined with dissociatives, the geometry, euphoria, dissociation and hallucinatory effects are often greatly enhanced. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] while under the influence of 2C-C have significantly more vivid visuals than dissociatives alone. It also results in more intense [[internal hallucinations]] and corresponding [[confusion]] which can develop into [[delusions]] and [[psychosis]]. | *'''[[Dissociatives]]''' - When combined with dissociatives, the geometry, euphoria, dissociation and hallucinatory effects are often greatly enhanced. Dissociative-induced [[Visual_disconnection#Holes.2C_spaces_and_voids|holes, spaces, and voids]] while under the influence of 2C-C have significantly more vivid visuals than dissociatives alone. It also results in more intense [[internal hallucinations]] and corresponding [[confusion]] which can develop into [[delusions]] and [[psychosis]]. | ||
*'''[[Nitrous]]''' - Nitrous oxide is commonly used in combination with psychedelics. The two are known to possess powerful cross-synergistic effects, including the capacity to send the user directly into an [[ego death|"ego death"]] state. The speed and intensity with which this occurs is very rapid and the euphoria that can result often leads to the urge to [[compulsive redosing|compulsively redose]]. | *'''[[Nitrous]]''' - Nitrous oxide is commonly used in combination with psychedelics. The two are known to possess powerful cross-synergistic effects, including the capacity to send the user directly into an [[ego death|"ego death"]] state. The speed and intensity with which this occurs is very rapid and the euphoria that can result often leads to the urge to [[compulsive redosing|compulsively redose]]. | ||
*'''[[MDMA]]''' - When combined with MDMA, the physical and cognitive effects of 2C-C become strongly amplified. The visual, physical and cognitive effects of 2C-C are also intensified with strong sensations of euphoric pleasure manifested through distinct body highs and headspaces, and uniquely colorful visuals. The synergy between these substances is unpredictable, and it is best to start with markedly lower dosages than one would take for both substances individually. This combination may increase the neurotoxic effects of MDMA based on its similarity to LSD, which has been found to increase MDMA neurotoxicity.<ref>Armstrong | *'''[[MDMA]]''' - When combined with MDMA, the physical and cognitive effects of 2C-C become strongly amplified. The visual, physical and cognitive effects of 2C-C are also intensified with strong sensations of euphoric pleasure manifested through distinct body highs and headspaces, and uniquely colorful visuals. The synergy between these substances is unpredictable, and it is best to start with markedly lower dosages than one would take for both substances individually. This combination may increase the neurotoxic effects of MDMA based on its similarity to LSD, which has been found to increase MDMA neurotoxicity.<ref>{{cite journal|last1=Armstrong|first1=B. D.|last2=Paik|first2=E.|last3=Chhith|first3=S.|last4=Lelievre|first4=V.|last5=Waschek|first5=J. A.|last6=Howard|first6=S. G.|date=October 26, 2004|title=Potentiation of (DL)‐3, 4‐methylenedioxymethamphetamine (MDMA)‐induced toxicity by the serotonin 2A receptior partial agonist d‐lysergic acid diethylamide (LSD), and the protection of same by the serotonin 2A/2C receptor antagonist MDL 11,939|journal=Neuroscience Research Communications|volume=35|issue=2|pages=83-95|doi=10.1002/nrc.20023|eissn=1520-6769}}</ref> | ||
*'''[[Alcohol]]''' - Alcohol can increase the disinhibiting and euphoric effects of 2C-C which lends to its use in recreational settings. It can be used in light doses to "take the edge off" a trip as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines. However, this is not typically recommended due to alcohol’s ability to cause [[dehydration]] and [[nausea]] and [[physical fatigue]] which can negatively affect a trip if taken in moderate to high dosages. Heavy drinking is strongly discouraged as it can easily lead to black outs and unpredictable behavior. | *'''[[Alcohol]]''' - Alcohol can increase the disinhibiting and euphoric effects of 2C-C which lends to its use in recreational settings. It can be used in light doses to "take the edge off" a trip as well as dull its psychedelic effects in a fashion somewhat similar to benzodiazepines. However, this is not typically recommended due to alcohol’s ability to cause [[dehydration]] and [[nausea]] and [[physical fatigue]] which can negatively affect a trip if taken in moderate to high dosages. Heavy drinking is strongly discouraged as it can easily lead to black outs and unpredictable behavior. | ||
*'''[[Benzodiazepines]]''' - Benzodiazepines can, depending on the dosage, slightly to completely reduce the intensity of the cognitive, physical and visual effects of a 2C-C trip. They are very efficient at stopping [[bad trip|"bad trips"]] at the cost of amnesia and reduced trip intensity. Caution is advised when acquiring them for this purpose due to their very high abuse and addiction potential. | *'''[[Benzodiazepines]]''' - Benzodiazepines can, depending on the dosage, slightly to completely reduce the intensity of the cognitive, physical and visual effects of a 2C-C trip. They are very efficient at stopping [[bad trip|"bad trips"]] at the cost of amnesia and reduced trip intensity. Caution is advised when acquiring them for this purpose due to their very high abuse and addiction potential. | ||
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{{#ask: [[Category:2C-C]][[Category:Experience]]|format=ul|Columns=1}} | {{#ask: [[Category:2C-C]][[Category:Experience]]|format=ul|Columns=1}} | ||
Additional experience reports can be found here: | Additional experience reports can be found here: | ||
* [https://www.erowid.org/experiences/subs/exp_2CC.shtml Erowid Experience Vaults: 2C-C] | |||
*[https://www.erowid.org/experiences/subs/exp_2CC.shtml Erowid Experience Vaults: 2C-C] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
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Although no formal studies have been conducted, it is not unreasonable to assume that like psychedelics in general, 2C-C is [[Addiction potential::not habit-forming]] and that the desire to use it can actually decrease with use. | Although no formal studies have been conducted, it is not unreasonable to assume that like psychedelics in general, 2C-C is [[Addiction potential::not habit-forming]] and that the desire to use it can actually decrease with use. | ||
Tolerance to the effects of 2C-C | Tolerance to the effects of 2C-C is not built almost immediately after ingestion. Similar to [[2C-B]] there seems to be no apparent tolerance buildup if used repeatedly for a few days. 2C-C does however produce cross-tolerance with other serotonergic psychedelics, meaning that after the use of 2C-C all psychedelics will have a reduced effect. | ||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
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==Legal status== | ==Legal status== | ||
*'''Australia | |||
*'''Austria | *'''Australia''': Australia has a blanket ban over all substituted phenethylamines including the entire 2C-X family.<ref>{{cite web|title=Psychoactive Substances|publisher=National Drug and Alcohol Research Centre|year=2014|url=https://comorbidity.edu.au/sites/default/files/cre/page/New%20Psychoactive%20Substances.pdf}}{{dead link|date=October 2020}}</ref> | ||
*'''Brazil | *'''Austria''': 2C-C is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich). In its Schedule II, the further specifying NPSV (Neue-Psychoaktive-Substanzen-Verordnung Österreich) explicitly bans all substituted phenetylamines.<ref>{{cite web|url=https://www.ris.bka.gv.at/GeltendeFassung.wxe?Abfrage=Bundesnormen&Gesetzesnummer=20007642|title=Bundesrecht konsolidiert: Gesamte Rechtsvorschrift für Neue-Psychoaktive-Substanzen-Verordnung|date=June 26, 2019|language=de|access-date=January 10, 2021}}</ref> | ||
*'''Canada | *'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>{{cite web|url=http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7|title=RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016|publication-date=December 5, 2016|publisher=Agência Nacional de Vigilância Sanitária (ANVISA) [Brazilian Health Regulatory Agency (ANVISA)]|language=pt}}</ref> | ||
*'''China | *'''Canada''': 2C-C would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>{{cite web|url=http://isomerdesign.com/Cdsa/schedule.php?schedule=3§ion=ALL&structure=C|title=Schedule III|work=Controlled Drugs and Substances Act (CDSA)|publisher=Isomer Design|access-date=October 10, 2020}}</ref> | ||
*'''Germany''': | *'''China''': As of October 2015, 2C-C is a controlled substance in China.<ref>{{cite web|url=http://www.sfda.gov.cn/WS01/CL0056/130753.html|title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知|publisher=国家食品药品监督管理总局 [China Food and Drug Administration (CFDA)]|date=September 27, 2015|language=zh|archive-url=https://web.archive.org/web/20170906191704/http://www.sfda.gov.cn/WS01/CL0056/130753.html|archive-date=September 6, 2017}}</ref> | ||
*'''Japan | *'''Germany''': 2C-C is controlled under Anlage I BtMG (''Narcotics Act, Schedule I'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> as of December 13, 2014.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl114s1999.pdf|title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 2014 Teil I Nr. 57|page=1999-2002|publication-date=December 12, 2014|language=de|oclc=231871244|issn=0341-1095|date=December 5, 2014}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: § 29|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> | ||
*'''Latvia | *'''Japan''': 2C-C is controlled by the Pharmaceutical Affairs Law in Japan, making it illegal to possess or sell.<ref>{{cite journal|title=Analytical Data of Designated Substances (Shitei-Yakubutsu) Controlled by the Pharmaceutical Affairs Law in Japan, Part I: GC-MS and LC-MS|url=https://www.erowid.org/references/texts/show/7395docid7635|language=ja|volume=128|issue=6|pages=971-979|journal=Yakugaku Zasshi|eissn=0031-6903|issn=1347-5231|oclc=909890652|year=2008|pmid=18520145|doi=10.1248/yakushi.128.981|first1=N.|last1=Uchiyama|first2=M.|last2=Kawamura|first3=H.|last3=Kamakura|first4=R.|last4=Kikura-Hanajiri|first5=Y.|last5=Goda}}</ref> | ||
*'''Sweden | *'''Latvia''': 2C-C is a Schedule I controlled substance in Latvia.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref> | ||
*'''Switzerland | *'''Sweden''': 2C-C is a controlled substance.<ref>{{cite web|title=Svensk författningssamling Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor|url=http://www.notisum.se/rnp/sls/sfs/20050026.pdf|id=SFS 2005:26|language=sv|date=February 3, 2005|publication-date=February 15, 2005|publisher=Läkemedelsverket [Swedish Medical Products Agency]|issn=1101-5225|work=Läkemedelsverkets författningssamling (LVFS)}}</ref> | ||
*'''United Kingdom | *'''Switzerland''': 2C-C is a controlled substance specifically named under Verzeichnis E.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | ||
*'''United States | *'''Turkey:''' 2C-C is classed as a drug and is illegal to possess, produce, supply, or import.<ref>Bakanlar Kurulu Kararı Karar Sayısı : 2013/4827 | https://free-ankara.org/wp-content/uploads/2017/09/BKK_2013_4827_28688.pdf</ref> | ||
*'''United Kingdom''': 2C-C is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.<ref>{{cite web|title=Schedule 2: Part I: Class A Drugs|url=http://www.legislation.gov.uk/ukpga/1971/38/schedule/2/part/I|work="Misuse of Drugs Act 1971"|access-date=August 20, 2020|publisher=UK Government}}</ref> | |||
*'''United States''': As of July 9, 2012, 2C-C is a Schedule I substance in the United States under the Food and Drug Administration Safety and Innovation Act of 2012, making possession, distribution and manufacture illegal without a DEA license.<ref>{{cite web|url=http://www.govtrack.us/congress/bills/112/s3187/text|title=S. 3187 (112<sup>th</sup>): Food and Drug Administration Safety and Innovation Act|date=June 27, 2012|access-date=October 10, 2020|publisher=GovTrack}}</ref> | |||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Psychedelic]] | *[[Psychedelic]] | ||
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==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/2C-C 2C-C (Wikipedia)] | *[https://en.wikipedia.org/wiki/2C-C 2C-C (Wikipedia)] | ||
*[https://erowid.org/chemicals/2cc/2cc.shtml 2C-C (Erowid Vault)] | *[https://erowid.org/chemicals/2cc/2cc.shtml 2C-C (Erowid Vault)] | ||
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=22 2C-C (PiHKAL / Isomer Design)] | *[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=22 2C-C (PiHKAL / Isomer Design)] | ||
===Discussion=== | ===Discussion=== | ||
*[http://www.bluelight.org/vb/threads/286447-The-Big-amp-Dandy-2C-C-Thread The Big & Dandy 2C-C Thread (Bluelight)] | *[http://www.bluelight.org/vb/threads/286447-The-Big-amp-Dandy-2C-C-Thread The Big & Dandy 2C-C Thread (Bluelight)] | ||
*[http://disregardeverythingisay.com/post/109207440089/2c-c-broken-down-and-described 2C-C, broken down and described (Disregard Everything I Say)] | *[http://disregardeverythingisay.com/post/109207440089/2c-c-broken-down-and-described 2C-C, broken down and described (Disregard Everything I Say)] | ||
==References== | ==References== | ||
<references/> | <references /> | ||
{{#set:Featured=true}} | {{#set:Featured=true}} | ||
[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Psychedelic]] | [[Category:Psychedelic]] | ||
[[Category: | [[Category:2C-x]] | ||
[[Category:Research chemical]] | |||