2C-C

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| _other_data=2-(4-chloro-2,5-dimethoxyphenyl)ethan-1-amine

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2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally, but may also be insufflated.<ref name="CitePiHKAL">Template:CitePiHKAL</ref> 2C-C 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>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Not much information is known about the toxicity of 2C-C.

Effects

Over the approximate dose range 20–40 mg, visual effects last approximately 4 to 8 hours.<ref name="CitePiHKAL"/>

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

Template:Nowrap

Target	Affinity (Ki, nM)
5-HT1A	190–740 (Ki) >10,000 (Template:Abbrlink) <25% (Template:Abbrlink)
5-HT1B	Template:Abbr
5-HT1D	Template:Abbr
5-HT1E	Template:Abbr
5-HT1F	Template:Abbr
5-HT2A	5.47–13 (Ki) 9.27–200 (Template:Abbr) 49–102% (Template:Abbr)
5-HT2B	Template:Abbr (Ki) 280 (Template:Abbr) 81% (Template:Abbr)
5-HT2C	5.4–90 (Ki) 24.2 (Template:Abbr) 94% (Template:Abbr)
5-HT3	Template:Abbr
5-HT4	Template:Abbr
5-HT5A	Template:Abbr
5-HT6	Template:Abbr
5-HT7	Template:Abbr
α1A	13,000
α1B, α1D	Template:Abbr
α2A	530
α2B, α2C	Template:Abbr
β1–β3	Template:Abbr
D1	13,000
D2	2,100
D3	17,000
D4	Template:Abbr
D5	Template:Abbr
H1	14,000
H2–H4	Template:Abbr
M1–M5	Template:Abbr
I1	Template:Abbr
σ1, σ2	Template:Abbr
Template:Abbrlink	4,100 (Ki) (mouse) 110 (Ki) (rat) 2,300 (Template:Abbr) (mouse) 340 (Template:Abbr) (rat) >10,000 (Template:Abbr) (human) 57% (Template:Abbr) (mouse) 51% (Template:Abbr) (rat)
Template:Abbrlink	24,000 (Ki) 72,000–74,000 (Template:Abbrlink) >100,000 (Template:Abbr) (rat)
Template:Abbrlink	>30,000 (Ki) 63,000–93,000 (Template:Abbr) 100,000 (Template:Abbr) (rat)
Template:Abbrlink	>30,000 (Ki) 305,000 (Template:Abbr) >100,000 (Template:Abbr) (rat)
Template:Abbrlink	Template:Abbr (Template:Abbr)
Template:Abbrlink	Template:Abbr (Template:Abbr)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="PDSPKiDatabase">{{#invoke:citation/CS1|citation		CitationClass=web }}</ref><ref name="BindingDB">{{#invoke:citation/CS1|citation	CitationClass=web }}</ref><ref name="RickliLuethiReinisch2015">Template:Cite journal</ref><ref name="EshlemanForsterWolfrum2014">Template:Cite journal</ref><ref name="NagaiNonakaSatohHisashiKamimura2007">Template:Cite journal</ref><ref name="RudinLuethiHoener2022">Template:Cite journal</ref><ref name="PottieCannaertStove2020">Template:Cite journal</ref><ref name="SimmlerBuchyChaboz2016">Template:Cite journal</ref>

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-HT_1A receptor with 15-fold lower affinity than for the serotonin 5-HT_2A 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" />

Society and culture

Legal status

China

As of October 2015 2C-C is a controlled substance in China.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Canada

As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.<ref>{{#invoke:citation/CS1|citation |CitationClass=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>{{#invoke:citation/CS1|citation |CitationClass=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">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

See also

• Phenethylamines
• DOC

External links

• 2C-C - Isomer Design
• 2C-C - PsychonautWiki
• Erowid 2C-C Vault
• 2C-C - PiHKAL - Erowid
• 2C-C - PiHKAL - Isomer Design
• 2C-C: “Euphoric, Lucid, & Highly Visual” - Tripsitter

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