2C-C
2C-C, also known as 4-chloro-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.<ref name="PiHKAL">Template:CitePiHKAL https://erowid.org/library/books_online/pihkal/pihkal022.shtml</ref> It is taken orally.<ref name="PiHKAL" />
2C-C was first described in the scientific literature by Alice Cheng and Neal Castagnoli in 1984.<ref name="ChengCastagnoli1984">Template:Cite journal</ref> It was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).<ref name="PiHKAL" /> The drug is Schedule I of section 202(c) of the Controlled Substances Act in the United States, signed into law as of July 2012 under the Food and Drug Administration Safety and Innovation Act.<ref>Template:Cite web</ref>
Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-C's dose range as 20 to 40Template:Nbspmg orally and its duration as 4 to 8Template:Nbsphours.<ref name="PiHKAL" /> Its onset is described as delayed compared to 2C-B and as being 1.5 to 2Template:Nbsphours.<ref name="PiHKAL" /> In addition to oral administration, a single report of 20Template:Nbspmg by intravenous injection was described as overwhelming, with effects peaking after 5Template:Nbspminutes and lasting perhaps 15Template:Nbspminutes.<ref name="PiHKAL" /> The effects of 2C-C have been reported to include psychedelic visuals, sensual enhancement, stimulation, sedation, and relaxation, among others.<ref name="PiHKAL" /> Its stimulating effects are said to be less than those of 2C-B and it is said to be sedating in some ways.<ref name="PiHKAL" />
Interactions
2C drugs like 2C-C are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="DeanStellpflugBurnett2013">Template:Cite journal</ref><ref name="TheobaldMaurer2007">Template:Cite journal</ref> Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-C.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">Template:Cite journal</ref> This may result in overdose and serious toxicity.<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />
Pharmacology
Pharmacodynamics
2C-C acts as an agonist of the serotonin 5-HT2 receptors.<ref name="Gil-MartinsBarbosaBorges2025">Template:Cite journal</ref><ref name="RickliLuethiReinisch2015" /> It also binds to the serotonin 5-HT1A receptor with 15-fold lower affinity than for the serotonin 5-HT2A receptor.<ref name="Gil-MartinsBarbosaBorges2025" /><ref name="RickliLuethiReinisch2015" /> The drug shows little or no affinity for the monoamine transporters (MATs) and shows very weak or negligible monoamine reuptake inhibition.<ref name="RickliLuethiReinisch2015" /><ref name="KimMaHur2021" /> It shows high affinity for the rat trace amine-associated receptor 1 (TAAR1), but only weak affinity for the mouse TAAR1.<ref name="Gil-MartinsBarbosaBorges2025" /><ref name="RickliLuethiReinisch2015" />
In contrast to many other psychedelics, 2C-C, as well as 2C-P and certain 2C NBOMe analogues, has shown reinforcing effects in rodents.<ref name="Gil-MartinsBarbosaBorges2025" /><ref name="KimMaHur2021">Template:Cite journal</ref> It produces dose-dependent conditioned place preference (CPP) in mice and self-administration in rats.<ref name="Gil-MartinsBarbosaBorges2025" /><ref name="KimMaHur2021" /> These findings suggest that 2C-C may have misuse potential.<ref name="Gil-MartinsBarbosaBorges2025" /><ref name="KimMaHur2021" /> The mechanism by which these effects are produced is unknown.<ref name="KimMaHur2021" /> However, 2C-C was found to decrease dopamine transporter (DAT) expression and to increase DAT phosphorylation in the nucleus accumbens and medial prefrontal cortex (mPFC) similarly to methamphetamine in rodents.<ref name="Gil-MartinsBarbosaBorges2025" /><ref name="KimMaHur2021" /> Decreased DAT expression may result in reduced dopamine reuptake, while DAT phosphorylation is associated with dopamine reverse transport and efflux, in turn increasing extracellular dopamine levels.<ref name="Gil-MartinsBarbosaBorges2025" /><ref name="KimMaHur2021" />
2C-C has also been found to produce neurotoxicity at high doses in rodents, which appears to be mediated via neuroinflammation.<ref name="KimMaHur2021" />
Chemistry
Synthesis
The chemical synthesis of 2C-C has been described.<ref name="PiHKAL" />
Analogues
Analogues of 2C-C include 2C-B, 2C-I, DOC, and 25C-NBOMe, among others.<ref name="PiHKAL" /><ref name="TrachselLehmannEnzensperger2013">Template:Cite book</ref>
History
2C-C was first described in the scientific literature by Alice Cheng and Neal Castagnoli in 1984.<ref name="ChengCastagnoli1984">Template:Cite journal</ref> It was described in greater detail, including its properties and effects in humans, by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).<ref name="PiHKAL" />
Society and culture
Legal status
China
As of October 2015 2C-C is a controlled substance in China.<ref>Template:Cite web</ref>
Canada
As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.<ref>Template:Cite web</ref>
Finland
Scheduled in the "government decree on psychoactive substances banned from the consumer market".<ref>Template:Cite web</ref>
Germany
2C-C is an Anlage I controlled drug.
Sweden
Sveriges riksdags health ministry Statens folkhälsoinstitut classified 2C-C as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as 2,5-dimetoxi-4-klorfenetylamin (2C-C), making it illegal to sell or possess.<ref>Template:Cite web</ref>
United States
As of July 9, 2012, in the United States 2C-C is a Schedule I substance under the Food and Drug Administration Safety and Innovation Act of 2012, making possession, distribution and manufacture illegal.<ref name="erowid-law">Template:Cite web</ref>
See also
References
External links
- 2C-C - Isomer Design
- 2C-C - PsychonautWiki
- 2C-C - Erowid
- 2C-C - PiHKAL - Erowid
- 2C-C - PiHKAL - Isomer Design
- 2C-C: “Euphoric, Lucid, & Highly Visual” - Tripsitter
Template:Psychedelics Template:Serotonin receptor modulators Template:TAAR modulators Template:Phenethylamines