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'''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 - PIHKAL | http://www.erowid.org/library/books_online/pihkal/pihkal033.shtml</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.
'''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, A. C., & Castagnoli Jr, N. (1984). Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2, 5-dihydroxyphenyl)-2-aminoethane analogs of 6-hydroxydopamine. Journal of medicinal chemistry, 27(4), 513-520. https://doi.org/10.1021/jm00370a014</ref> Its activity in humans was later investigated and documented by [[Alexander Shulgin]] in his book [[PiHKAL]] ("Phenethylamines I Have Known and Loved").
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 considered to be 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.
Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-C, and its history of human use is limited. Today, it is used for [[recreational drug use|recreational]] and therapeutic purposes. It is rarely sold on the streets and distributed online as a grey area [[research chemical]].
Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-C, and its history of human use is limited. Today, it is used for [[recreational drug use|recreational]] and therapeutic purposes. It is rarely sold on the streets and distributed online as a grey area [[research chemical]].
==Chemistry==
==Chemistry==
[[File:Phenethylamine.png|thumb|right|253px|thumb|right|253px||Generic structure of a phenethylamine molecule]]
[[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="isomer">2,5-Dimethoxy-4-chlorophenethylamine (Isomer Design / PiHKAL) | http://isomerdesign.com/PiHKAL/read.php?id=22</ref>
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 lacks the distinctive energetic feeling associated with most [[phenethylamines]]. This is described in [[PiHKAL]] as "''an intense form of relaxation.''"<ref name="isomer">2,5-Dimethoxy-4-chlorophenethylamine (Isomer Design / PiHKAL) | http://isomerdesign.com/PiHKAL/read.php?id=22</ref>
*'''[[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::Tactile enhancement]]'''
*'''[[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.
*'''[[Effect::Increased heart rate]]''' - This compound seems to not increase heart rate as much as related substances.
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Muscle cramps]]''' - Very high dosages of 2C-C are known to cause random muscle tightening, which can become uncomfortable.
*'''[[Effect::Nausea]]''' - Although nausea remains present, in comparison to other [[phenethylamines]] such as [[2C-E]], [[2C-I]] or [[2C-B]], this remains relatively mild and tends to dissipate quickly. It is considered by some to be one of the most physically understated [[psychedelics]] known.
*'''[[Effect::Nausea]]''' - Although nausea remains present, in comparison to other [[phenethylamines]] such as [[2C-E]], [[2C-I]] or [[2C-B]], this remains relatively mild and tends to dissipate quickly. It is considered by some to be one of the most physically understated [[psychedelics]] known.
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]].
*'''[[Effect::Teeth grinding]]''' - This component can be considered to be less intense when compared with that of [[MDMA]].
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Flowing|flowing]], [[Drifting#Breathing|breathing]] and [[Drifting#morphing|morphing]])'' - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance and realistic in style.
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Flowing|flowing]], [[Drifting#Breathing|breathing]] and [[Drifting#morphing|morphing]])'' - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance and cartoon-like in style.
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Tracers]]'''
*'''[[Effect::Tracers]]'''
====[[Effect::Geometry]]====
The visual geometry of 2C-C is more similar in appearance to that of [[2C-B]] than that of [[Psilocin]], [[2C-E]], or [[ayahuasca]]. They can be comprehensively described as unstructured in their organization, algorithmic in geometric style, intricate in complexity, large, fast and smooth in motion, colorful in scheme, glossy in color, sharp in their edges and angular in their corners.
====Hallucinatory states====
====Hallucinatory states====
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*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::Internal hallucination]]''' (''[[Effect::autonomous entities]]''; ''[[Effect::settings, sceneries, and landscapes]]''; ''[[Effect::perspective hallucinations]]'' and ''[[Effect::scenarios and plots]]'') - 2C-C is capable of producing high levels of hallucinogenic imagery, although typically only at very heavy doses. When this effect does occur, it commonly contains hallucinations with scenarios, settings, concepts and autonomous entity contact. They are more common within dark environments and can be described as internal in their manifestation, lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in theme.
*'''[[Effect::Internal hallucination]]''' (''[[Effect::autonomous entities]]''; ''[[Effect::settings, sceneries, and landscapes]]''; ''[[Effect::perspective hallucinations]]'' and ''[[Effect::scenarios and plots]]'') - 2C-C is capable of producing high levels of hallucinogenic imagery, although typically only at very heavy doses. When this effect does occur, it commonly contains hallucinations with scenarios, settings, concepts and autonomous entity contact. They are more common within dark environments and can be described as internal in their manifestation, lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in theme.
*'''[[Effect::External hallucinations]]''' (''[[Effect::autonomous entities]]''; ''[[Effect::settings, sceneries, and landscapes]]''; ''[[Effect::perspective hallucinations]]'' and ''[[Effect::scenarios and plots]]'') - 2C-C is capable of external hallucinations embedded within visual geometry. This particular effect commonly contains hallucinations with scenarios, settings, concepts and autonomous entity contact. They can be described as external in their manifestation, lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
*'''[[Effect::External hallucination]]''' (''[[Effect::autonomous entities]]''; ''[[Effect::settings, sceneries, and landscapes]]''; ''[[Effect::perspective hallucinations]]'' and ''[[Effect::scenarios and plots]]'') - 2C-C is capable of external hallucinations embedded within visual geometry. This particular effect commonly contains hallucinations with scenarios, settings, concepts and autonomous entity contact. They can be described as external in their manifestation, lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
}}
}}
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The head space of 2C-C is described by many as one which is both insightful and relatively normal in its thought processes even at moderate to high dosages.
The head space of 2C-C is described by many as one which is both insightful and relatively normal in its thought processes even at moderate to high dosages.
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - This component is consistently manifested only in the context of social settings in which one is within the company of others. These feelings of sociability, love and empathy are not as pronounced than those found on substances such as [[MDMA]] or [[2C-B]]. They primarily manifest during the stimulating onset of the experience and dissipate during the peak and offset.
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - This component is consistently manifested only in the context of social settings in which one is within the company of others. These feelings of sociability, love and empathy are not as pronounced than those found on substances such as [[MDMA]] or [[2C-B]].
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Analysis enhancement]]''' - This [[introspection]] dominant effect is only manifested consistently in the context of a non-social setting in which the user is alone.
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Emotion enhancement]]'''
*'''[[Effect::Emotion enhancement]]'''
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*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Memory suppression]]''' - Relative to other psychedelics, 2C-C does not produce this effect except at high doses.
*'''[[Effect::Increased sense of humor]]'''
**'''[[Effect::Ego death]]''' - Relative to other psychedelics, 2C-C does not produce this effect except at high doses.
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Mindfulness]]
*'''[[Effect::Memory suppression]]''' - Relative to other psychedelics, 2C-C does not produce this effect except at very high doses.
**'''[[Effect::Ego death]]''' - Relative to other psychedelics, 2C-C does not produce this effect except at very high doses.
*'''[[Effect::Mindfulness]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Personal bias suppression]]'''
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*'''[[Effect::Thought connectivity]]'''
*'''[[Effect::Thought connectivity]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]''' - Due to it's relaxing nature, some users report being able to sleep after the peak effects subsided.
}}
}}
{{effects/auditory|
{{effects/auditory|
*'''[[Effect::Auditory enhancement]]'''
*'''[[Effect::Auditory enhancement]]'''
*'''[[Effect::Auditory distortion]]''' - This effect does not typically occur except at very high doses.
*'''[[Effect::Auditory distortion]]''' - This effect does not typically occur except at higher doses.
*'''[[Effect::Auditory hallucinations]]''' - This effect does not typically occur except at very high doses.
*'''[[Effect::Auditory hallucination]]''' - This effect does not typically occur except at higher doses.
}}
}}
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}}
}}
}}
}}
===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.
*'''[[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]].
*'''[[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.
*'''[[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.
*'''[[Psychedelics]]''' - When used in combination with other psychedelics, each substance's physical, cognitive and visual effects intensify and synergize strongly. The synergy between those substances is unpredictable, and for this reason generally not advised. If choosing to combine psychedelics, it is recommended to start with significantly lower dosages than one would take for either substance individually.
===Experience reports===
===Experience reports===
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
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 are built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). 2C-C presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 2C-C all psychedelics will have a reduced effect.
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===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Psychedelics}}
*'''[[Tramadol]]''' - Tramadol lowers the seizure threshold<ref>Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089</ref> and [[psychedelics]] may act as triggers for seizures, particularly in those who are predisposed to them.{{citation needed}}
==Legal status==
*'''[[Stimulants]]''' - Combining stimulants with psychedelics may induce states of uncontrollable [[anxiety]], over-stimulation, [[thought loops]], and increase the risk of psychosis.<ref>Tripsit Factsheets - LSD | http://drugs.tripsit.me/lsd</ref>
*'''[https://en.wikipedia.org/wiki/Lithium_(medication) Lithium]''' - Lithium is often used as treatment for bipolar disorder. It may possibly cause elevated risk of seizures and psychosis due to its [[Glutamate|glutaminergic]] and [[GABA|GABAergic]] effects.{{citation needed}}
==Legal status==
*'''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>
*'''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>
*'''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>
*'''Brazil:''' Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref>
*'''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>
*'''Canada:''' 2C-C would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>Controlled Drugs and Substances Act (S.C. 1996, c. 19) |http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-12.html#h-28</ref>
*'''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>
*'''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=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}}</ref>
*'''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>
*'''Germany''': On December 13, 2014 2C-C was added to the controlled substance act ("BtMG"), making it illegal to produce, sell or possess.<ref>Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften (28. BtMÄndV)| http://www.buzer.de/gesetz/11392/a189949.htm</ref>
*'''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>
*'''Japan:''' 2C-C is controlled by the Pharmaceutical Affairs Law in Japan, making it illegal to possess or sell.<ref>Analytical Data of Designated Substances (Shitei-Yakubutsu) Controlled by the Pharmaceutical AŠairs Law in Japan, Part I: GC-MS and LC-MS | https://www.erowid.org/references/texts/show/7395docid7635</ref>
*'''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>
*'''Latvia:''' 2C-C is a Schedule I controlled substance.<ref>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086</ref>
*'''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>
*'''Sweden:''' 2C-C is classified as a health hazard as of March 1, 2005 in the regulation SFS 2005:26, making it illegal to sell or possess.<ref>Svensk författningssamling | http://www.notisum.se/rnp/sls/sfs/20050026.pdf</ref>
*'''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>
*'''Switzerland:''' Possession, production and sale is illegal.<ref>http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html</ref>
*'''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 Kingdom:''' 2C-C is a Class A drug 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>
*'''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 States:''' 2C-C is listed in Schedule I of section 202(c) of the Controlled Substances Act in the United States. This was signed into law as of July 2012 under the Food and Drug Administration Safety and Innovation Act.<ref>S. 3187: Food and Drug Administration Safety and Innovation Act, Subtitle D-Synthetic Drugs | http://www.govtrack.us/congress/bills/112/s3187/text</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>
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
4-Chloro-2,5-dimethoxyphenethylamine (commonly known as 2C-C) is a lesser-known psychedelic substance of the phenethylamine class that produces psychedelic effects when administered.[1] 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.[2] 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 sedating than other closely related psychedelicphenethylamines 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.
Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-C, and its history of human use is limited. Today, it is used for recreational and therapeutic purposes. It is rarely sold on the streets and distributed online as a grey area research chemical.
2C-C or 2,5-dimethoxy-4-chlorophenethylamine is a substituted phenethylamine featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain. 2C-C contains methoxy functional groups CH3O- attached to carbons R2 and R5 as well as a chlorine atom attached to carbon R4 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.[1]
2C-C's psychedelic effects are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience is the subject of ongoing scientific investigation.
Subjective effects
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWikicontributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
Physical effects
Stimulation & 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."[1]
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.
Bodily control enhancement - Whilst at lower doses one may find that their bodily control is enhanced, at higher dosages this becomes suppressed.
Muscle cramps - Very high dosages of 2C-C are known to cause random muscle tightening, which can become uncomfortable.
Nausea - Although nausea remains present, in comparison to other phenethylamines such as 2C-E, 2C-I or 2C-B, this remains relatively mild and tends to dissipate quickly. It is considered by some to be one of the most physically understated psychedelics known.
Drifting(melting, flowing, breathing and morphing) - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance and cartoon-like in style.
The visual geometry of 2C-C is more similar in appearance to that of 2C-B than that of Psilocin, 2C-E, or ayahuasca. They can be comprehensively described as unstructured in their organization, algorithmic in geometric style, intricate in complexity, large, fast and smooth in motion, colorful in scheme, glossy in color, sharp in their edges and angular in their corners.
Hallucinatory states
2C-C can produce a full range of hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used psychedelics. However, the dose required to reach this state is significantly higher than many related 2C-x phenethylamines. These effects include:
Internal hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations and scenarios and plots) - 2C-C is capable of producing high levels of hallucinogenic imagery, although typically only at very heavy doses. When this effect does occur, it commonly contains hallucinations with scenarios, settings, concepts and autonomous entity contact. They are more common within dark environments and can be described as internal in their manifestation, lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in theme.
External hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations and scenarios and plots) - 2C-C is capable of external hallucinations embedded within visual geometry. This particular effect commonly contains hallucinations with scenarios, settings, concepts and autonomous entity contact. They can be described as external in their manifestation, lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
Cognitive effects
The head space of 2C-C is described by many as one which is both insightful and relatively normal in its thought processes even at moderate to high dosages.
Empathy, affection, and sociability enhancement - This component is consistently manifested only in the context of social settings in which one is within the company of others. These feelings of sociability, love and empathy are not as pronounced than those found on substances such as MDMA or 2C-B.
Analysis enhancement - This introspection dominant effect is only manifested consistently in the context of a non-social setting in which the user is alone.
Unity and interconnectedness - In contrast to some other psychedelics, this effect does not typically occur except at very high doses.
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.
Dissociatives - When combined with dissociatives, the geometry, euphoria, dissociation and hallucinatory effects are often greatly enhanced. Dissociative-induced 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" state. The speed and intensity with which this occurs is very rapid and the euphoria that can result often leads to the urge to 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.[3]
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 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.
Psychedelics - When used in combination with other psychedelics, each substance's physical, cognitive and visual effects intensify and synergize strongly. The synergy between those substances is unpredictable, and for this reason generally not advised. If choosing to combine psychedelics, it is recommended to start with significantly lower dosages than one would take for either substance individually.
Experience reports
Anecdotal reports which describe the effects of this compound within our experience index include:
The toxicity and long-term health effects of recreational 2C-C use do not appear to have been studied in any scientific context and the exact toxic dose is unknown. This is because 2C-C is a research chemical with a limited history of human use.
Anecdotal reports from those who have tried this compound suggest that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (although nothing can be completely guaranteed). Independent research should always be conducted to ensure that a combination of two or more substances is safe before consumption.
Although no formal studies have been conducted, it is not unreasonable to assume that like psychedelics in general, 2C-C is not habit-forming and that the desire to use it can actually decrease with use.
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
Warning:Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
[[Wikipedia:Lithium_(medication)|DangerousInteraction::Lithium]] - Lithium is commonly prescribed for the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
"[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of 2C-C. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid unintentional overdose.
"[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is well-documented to lower the seizure threshold[4] and psychedelics may act to trigger seizures in susceptible individuals.[citation needed]
Legal status
Australia: Australia has a blanket ban over all substituted phenethylamines including the entire 2C-X family.[5]
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.[6]
Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[7]
Canada: 2C-C would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.[8]
China: As of October 2015, 2C-C is a controlled substance in China.[9]
Germany: 2C-C is controlled under Anlage I BtMG (Narcotics Act, Schedule I)[10] as of December 13, 2014.[11] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[12]
Japan: 2C-C is controlled by the Pharmaceutical Affairs Law in Japan, making it illegal to possess or sell.[13]
Latvia: 2C-C is a Schedule I controlled substance in Latvia.[14]
Switzerland: 2C-C is a controlled substance specifically named under Verzeichnis E.[16]
Turkey: 2C-C is classed as a drug and is illegal to possess, produce, supply, or import.[17]
United Kingdom: 2C-C is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.[18]
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.[19]
↑Cheng, A. C.; Castagnoli Jr, N. (1984). "Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2, 5-dihydroxyphenyl)-2-aminoethane analogs of 6-hydroxydopamine". Journal of Medicinal Chemistry. 27 (4): 513–520. doi:10.1021/jm00370a014. eISSN1520-4804. ISSN0022-2623. OCLC39480771. PMID6423824.
↑Armstrong, B. D.; Paik, E.; Chhith, S.; Lelievre, V.; Waschek, J. A.; Howard, S. G. (October 26, 2004). "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". Neuroscience Research Communications. 35 (2): 83–95. doi:10.1002/nrc.20023. eISSN1520-6769.
↑Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. ISSN1556-9039.
↑"Schedule III". Controlled Drugs and Substances Act (CDSA). Isomer Design. Retrieved October 10, 2020.
↑"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in 中文). 国家食品药品监督管理总局 [China Food and Drug Administration (CFDA)]. September 27, 2015. Archived from the original on September 6, 2017.
