Editing 2C-C

{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 477216097
| drug_name = 
| image = 2C-C.svg
| width = 200px
| caption = 
| image2 = 2C-C-3d-sticks.png
| width2 = 175px

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| routes_of_administration = [[Oral administration|Oral]]
| class = [[Serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| ATC_prefix = 
| ATC_suffix = 

<!-- Legal status -->
| legal_AU = 
| legal_BR = F2
| legal_CA = Schedule III
| legal_DE = Anlage I
| legal_US = Schedule I
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = 
| elimination_half-life = 
| duration_of_action = 
| excretion = 

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 88441-14-9
| CAS_supplemental = 
| PubChem = 29979100
| PubChemSubstance = 
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106221
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0RO7MZY2LS
| KEGG = 
| ChEBI = 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 124733
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 2,5-Dimethoxy-4-chlorophenethylamine; 4-Chloro-2,5-dimethoxyphenethylamine

<!-- Chemical data -->
| IUPAC_name = 2-(4-chloro-2,5-dimethoxyphenyl)ethan-1-amine
| C=10 | H=14 | Cl=1 | N=1 | O=2 
| SMILES = COc1cc(CCN)c(cc1Cl)OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H14ClNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CGKQFIWIPSIVAS-UHFFFAOYSA-N

<!-- Physical data -->
| melting_point = 220
| melting_high = 221
| melting_notes = ([[hydrochloride]])
}}

'''2C-C''' is a [[Psychedelics, dissociatives and deliriants|psychedelic drug]] of the [[2C (psychedelics)|2C family]]. It was first synthesized by [[Alexander Shulgin]], sometimes used as an [[entheogen]]. In his book ''[[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]]'', Shulgin lists the dosage range as 20–40&nbsp;mg. 2C-C is usually taken orally, but may also be insufflated.<ref name="CitePiHKAL">{{CitePiHKAL}}</ref> 2C-C is [[Controlled Substances Act#Schedule I controlled substances|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>{{cite web|url=http://www.govtrack.us/congress/bills/112/s3187/text|title=S. 3187: Food and Drug Administration Safety and Innovation Act, Subtitle D-Synthetic Drugs|publisher=FDA|date=June 27, 2012|access-date=July 12, 2012|url-status=live|archive-url=https://web.archive.org/web/20120704120359/http://www.govtrack.us/congress/bills/112/s3187/text|archive-date=July 4, 2012}}</ref>

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

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

==Interactions==
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

2C drugs like 2C-C are known to be [[drug metabolism|metabolized]] by the [[monoamine oxidase]] (MAO) [[enzyme]]s [[MAO-A]] and [[MAO-B]].<ref name="DeanStellpflugBurnett2013">{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}</ref><ref name="TheobaldMaurer2007">{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }}</ref> [[Monoamine oxidase inhibitor]]s (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">{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}}</ref> This may result in [[overdose]] and serious [[toxicity]].<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />

==Pharmacology==
{| class="wikitable floatleft" style="font-size:small;"
|+ {{Nowrap|2C-C activities}}
|-
! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM)
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 190–740 (K<sub>i</sub>)<br />>10,000 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br /><25% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT1F receptor|5-HT<sub>1F</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 5.47–13 (K<sub>i</sub>)<br />9.27–200 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />49–102% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || {{Abbr|ND|No data}} (K<sub>i</sub>)<br />280 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />81% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 5.4–90 (K<sub>i</sub>)<br />24.2 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />94% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT3 receptor|5-HT<sub>3</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]] || {{Abbr|ND|No data}}
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || 13,000
|-
| [[Alpha-1B adrenergic receptor|α<sub>1B</sub>]], [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || {{Abbr|ND|No data}}
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 530
|-
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]], [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || {{Abbr|ND|No data}}
|-
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]]–[[Beta-3 adrenergic receptor|β<sub>3</sub>]] || {{Abbr|ND|No data}}
|-
| [[D1 receptor|D<sub>1</sub>]] || 13,000
|-
| [[D2 receptor|D<sub>2</sub>]] || 2,100
|-
| [[D3 receptor|D<sub>3</sub>]] || 17,000
|-
| [[D4 receptor|D<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[D5 receptor|D<sub>5</sub>]] || {{Abbr|ND|No data}}
|-
| [[H1 receptor|H<sub>1</sub>]] || 14,000
|-
| [[H2 receptor|H<sub>2</sub>]]–[[H4 receptor|H<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]]–[[Muscarinic acetylcholine M5 receptor|M<sub>5</sub>]] || {{Abbr|ND|No data}}
|-
| [[I1 receptor|I<sub>1</sub>]] || {{Abbr|ND|No data}}
|-
| [[Sigma-1 receptor|σ<sub>1</sub>]], [[Sigma-2 receptor|σ<sub>2</sub>]] || {{Abbr|ND|No data}}
|-
| {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || 4,100 (K<sub>i</sub>) (mouse)<br />110 (K<sub>i</sub>) (rat)<br />2,300 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (mouse)<br />340 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)<br />>10,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (human)<br />57% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (mouse)<br />51% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (rat)
|-
| {{Abbrlink|SERT|Serotonin transporter}} || 24,000 (K<sub>i</sub>)<br />72,000–74,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)
|-
| {{Abbrlink|NET|Norepinephrine transporter}} || >30,000 (K<sub>i</sub>)<br />63,000–93,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)
|-
| {{Abbrlink|DAT|Dopamine transporter}} || >30,000 (K<sub>i</sub>)<br />305,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br />>100,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)
|-
| {{Abbrlink|MAO-A|Monoamine oxidase A}} || {{Abbr|ND|No data}} ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|-
| {{Abbrlink|MAO-B|Monoamine oxidase B}} || {{Abbr|ND|No data}} ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|- class="sortbottom"
| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''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">{{cite web | title=Kᵢ Database | website=PDSP | date=16 March 2025 | url=https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14697&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14669&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=16 March 2025}}</ref><ref name="BindingDB">{{cite web | last=Liu | first=Tiqing | title=BindingDB BDBM50240789 2-(4-Chloro-2,5-dimethoxy-phenyl)-ethylamine::2-(4-chloro-2,5-dimethoxyphenyl)ethylamine::CHEMBL124733 | website=BindingDB | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50240789 | access-date=16 March 2025}}</ref><ref name="RickliLuethiReinisch2015">{{cite journal | vauthors = Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | volume = 99 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf}}</ref><ref name="EshlemanForsterWolfrum2014">{{cite journal | vauthors = Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB | title = Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function | journal = Psychopharmacology (Berl) | volume = 231 | issue = 5 | pages = 875–888 | date = March 2014 | pmid = 24142203 | pmc = 3945162 | doi = 10.1007/s00213-013-3303-6 | url = https://www.researchgate.net/profile/Michael-Forster-2/publication/258061356_Behavioral_and_neurochemical_pharmacology_of_six_psychoactive_substituted_phenethylamines_Mouse_locomotion_rat_drug_discrimination_and_in_vitro_receptor_and_transporter_binding_and_function/links/53d119a00cf2f7e53cfbcd68/Behavioral-and-neurochemical-pharmacology-of-six-psychoactive-substituted-phenethylamines-Mouse-locomotion-rat-drug-discrimination-and-in-vitro-receptor-and-transporter-binding-and-function.pdf}}</ref><ref name="NagaiNonakaSatohHisashiKamimura2007">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = Eur J Pharmacol | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=00665d67c36dcf1777989b70cc901c654420a0c7| url-access = subscription }}</ref><ref name="RudinLuethiHoener2022">{{cite journal | vauthors = Rudin D, Luethi D, Hoener MC, Liechti ME | title=Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues | journal=The FASEB Journal | volume=36 | issue=S1 | date=2022 | issn=0892-6638 | doi=10.1096/fasebj.2022.36.S1.R2121 | doi-access=free | url=https://www.researchgate.net/publication/360423277_Structure-activity_relation_of_halogenated_25-dimethoxyamphetamines_compared_to_their_a-desmethyl_2C_analogues}}</ref><ref name="PottieCannaertStove2020">{{cite journal | vauthors = Pottie E, Cannaert A, Stove CP | title = In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor | journal = Arch Toxicol | volume = 94 | issue = 10 | pages = 3449–3460 | date = October 2020 | pmid = 32627074 | doi = 10.1007/s00204-020-02836-w | bibcode = 2020ArTox..94.3449P | url = | hdl = 1854/LU-8687071 | hdl-access = free }}</ref><ref name="SimmlerBuchyChaboz2016">{{cite journal | vauthors = Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME | title = In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 | journal = J Pharmacol Exp Ther | volume = 357 | issue = 1 | pages = 134–144 | date = April 2016 | pmid = 26791601 | doi = 10.1124/jpet.115.229765 | url = https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | archive-url = https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA | url-status = dead | archive-date = 2025-05-09 }}</ref>
|}

2C-C acts as an [[agonist]] of the [[serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]]s.<ref name="Gil-MartinsBarbosaBorges2025">{{cite journal | vauthors = Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R | title = Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential? | journal = Toxicol Rep | volume = 14 | issue = | pages = 101890 | date = June 2025 | pmid = 39867514 | doi = 10.1016/j.toxrep.2025.101890 | url = | pmc = 11762925 }}</ref><ref name="RickliLuethiReinisch2015" /> It also binds to the serotonin [[5-HT1A receptor|5-HT<sub>1A</sub> receptor]] with 15-fold lower [[affinity (pharmacology)|affinity]] than for the serotonin [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]].<ref name="Gil-MartinsBarbosaBorges2025" /><ref name="RickliLuethiReinisch2015" /> The drug shows little or no affinity for the [[monoamine transporter]]s (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]] [[structural analog|analogue]]s, has shown [[positive reinforcement|reinforcing]] effects in rodents.<ref name="Gil-MartinsBarbosaBorges2025" /><ref name="KimMaHur2021">{{cite journal | vauthors = Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG | title = New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents | journal = Arch Toxicol | volume = 95 | issue = 4 | pages = 1413–1429 | date = April 2021 | pmid = 33515270 | doi = 10.1007/s00204-021-02980-x | url = }}</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 of action|mechanism]] by which these effects are produced is unknown.<ref name="KimMaHur2021" /> However, 2C-C was found to decrease [[dopamine transporter]] (DAT) [[gene expression|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 pump|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==
==Analogues and derivatives==
{{2C-C analogues and derivatives}}

==Society and culture==
===Legal status===
====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=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

====Canada====
As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.<ref>{{Cite web|url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|title=Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|date=4 May 2016}}</ref>

====Germany====
2C-C is an [[Drugs controlled by the German Betäubungsmittelgesetz|Anlage I]] controlled drug.

====Sweden====
[[Riksdag|''Sveriges riksdags'']] health ministry [[:sv:Statens folkhälsoinstitut|''Statens folkhälsoinstitut'']] classified 2C-C as "health hazard" under the act [[:sv:Lagen om förbud mot vissa hälsofarliga varor|''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>{{cite web |url=http://www.notisum.se/rnp/sls/sfs/20050026.pdf |title=20050026 |access-date=2017-03-24 |url-status=live |archive-url=https://web.archive.org/web/20130929063138/http://www.notisum.se/rnp/sls/sfs/20050026.pdf |archive-date=2013-09-29 }}</ref>

====United States====
As of July 9, 2012, in the [[United States]] 2C-C is a [[Controlled Substances Act#Schedule I controlled substances|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">{{cite web|url=http://www.erowid.org/chemicals/2cc/2cc_law.shtml|title=Erowid 2C-C Vault : Legal Status|website=www.erowid.org|url-status=live|archive-url=https://web.archive.org/web/20140602055811/http://www.erowid.org/chemicals/2cc/2cc_law.shtml|archive-date=2014-06-02}}</ref>

==See also==
* [[Phenethylamine]]s
* [[2,5-Dimethoxy-4-chloroamphetamine|DOC]]

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/22 2C-C - Isomer Design]
* [https://psychonautwiki.org/wiki/2C-C 2C-C - PsychonautWiki]
* [http://www.erowid.org/chemicals/2cc/2cc.shtml Erowid 2C-C Vault]
* [https://erowid.org/library/books_online/pihkal/pihkal022.shtml 2C-C - PiHKAL - Erowid]
* [https://isomerdesign.com/pihkal/read/pk/22 2C-C - PiHKAL - Isomer Design]
* [https://tripsitter.com/2cc/ 2C-C: “Euphoric, Lucid, & Highly Visual” - Tripsitter]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}

{{DEFAULTSORT:2c-C}}

[[Category:2C (psychedelics)]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:5-HT2C agonists]]
[[Category:Chlorobenzene derivatives]]
[[Category:Designer drugs]]
[[Category:TAAR1 modulators]]