: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
| pronounce =
| tradename =
| Drugs.com =
| MedlinePlus =
| licence_CA =
| licence_EU =
| DailyMedID =
| licence_US =
| pregnancy_AU =
| pregnancy_category =
| dependency_liability =
| addiction_liability =
| routes_of_administration = Oral
| class = Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
| ATC_prefix =
| ATC_suffix =
| legal_AU =
| legal_BR = F2
| legal_CA = Schedule III
| legal_DE = Anlage I
| legal_US = Schedule I
| legal_status =
| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action =
| excretion =
| 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
| 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
| melting_point = 220
| melting_high = 221
| melting_notes = (hydrochloride)
}}
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.{{CitePiHKAL}} 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.{{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}}
Not much information is known about the toxicity of 2C-C.
Effects
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
2C drugs like 2C-C are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.{{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 = }}{{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 = }} Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-C.{{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}} This may result in overdose and serious toxicity.
Pharmacology
2C-C acts as an agonist of the serotonin 5-HT2 receptors.{{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 }} It also binds to the serotonin 5-HT1A receptor with 15-fold lower affinity than for the serotonin 5-HT2A receptor. The drug shows little or no affinity for the monoamine transporters (MATs) and shows very weak or negligible monoamine reuptake inhibition. It shows high affinity for the rat trace amine-associated receptor 1 (TAAR1), but only weak affinity for the mouse TAAR1.
In contrast to many other psychedelics, 2C-C, as well as 2C-P and certain 2C NBOMe analogues, has shown reinforcing effects in rodents.{{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 = }} It produces dose-dependent conditioned place preference (CPP) in mice and self-administration in rats. These findings suggest that 2C-C may have misuse potential. The mechanism by which these effects are produced is unknown. 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. 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.
2C-C has also been found to produce neurotoxicity at high doses in rodents, which appears to be mediated via neuroinflammation.
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.{{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 }}
==Canada==
As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.{{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}}
==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.{{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 }}
==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.{{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}}
See also
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}}