Chemistry:2C-C

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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.[1] 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.[2]

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.[1]

Interactions

2C drugs like 2C-C are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.[3][4] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-C.[3][4][5] This may result in overdose and serious toxicity.[5][3]

Pharmacology

2C-C activities
Target Affinity (Ki, nM)
5-HT1A 190–740 (Ki)
>10,000 (EC50)
<25% (Emax)
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 5.47–13 (Ki)
9.27–200 (EC50)
49–102% (Emax)
5-HT2B ND (Ki)
280 (EC50)
81% (Emax)
5-HT2C 5.4–90 (Ki)
24.2 (EC50)
94% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 ND
α1A 13,000
α1B, α1D ND
α2A 530
α2B, α2C ND
β1–β3 ND
D1 13,000
D2 2,100
D3 17,000
D4 ND
D5 ND
H1 14,000
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
TAAR1 4,100 (Ki) (mouse)
110 (Ki) (rat)
2,300 (EC50) (mouse)
340 (EC50) (rat)
>10,000 (EC50) (human)
57% (Emax) (mouse)
51% (Emax) (rat)
SERT 24,000 (Ki)
72,000–74,000 (IC50)
>100,000 (EC50) (rat)
NET >30,000 (Ki)
63,000–93,000 (IC50)
100,000 (EC50) (rat)
DAT >30,000 (Ki)
305,000 (IC50)
>100,000 (EC50) (rat)
MAO-A ND (IC50)
MAO-B ND (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [6][7][8][9][10][11][12][13]

2C-C acts as an agonist of the serotonin 5-HT2 receptors.[14][8] It also binds to the serotonin 5-HT1A receptor with 15-fold lower affinity than for the serotonin 5-HT2A receptor.[14][8] The drug shows little or no affinity for the monoamine transporters (MATs) and shows very weak or negligible monoamine reuptake inhibition.[8][15] It shows high affinity for the rat trace amine-associated receptor 1 (TAAR1), but only weak affinity for the mouse TAAR1.[14][8]

In contrast to many other psychedelics, 2C-C, as well as 2C-P and certain 2C NBOMe analogues, has shown reinforcing effects in rodents.[14][15] It produces dose-dependent conditioned place preference (CPP) in mice and self-administration in rats.[14][15] These findings suggest that 2C-C may have misuse potential.[14][15] The mechanism by which these effects are produced is unknown.[15] 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.[14][15] 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.[14][15]

2C-C has also been found to produce neurotoxicity at high doses in rodents, which appears to be mediated via neuroinflammation.[15]

Chemistry

Analogues and derivatives

Analogues and derivatives of 2C-C:

25C-NB*:

Society and culture

China

As of October 2015 2C-C is a controlled substance in China.[16]

Canada

As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.[17]

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".[18]

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.[19]

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.[20]

See also

References

  1. ↑ 1.0 1.1 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. 
  2. ↑ "S. 3187: Food and Drug Administration Safety and Innovation Act, Subtitle D-Synthetic Drugs". FDA. June 27, 2012. http://www.govtrack.us/congress/bills/112/s3187/text. 
  3. ↑ 3.0 3.1 3.2 "2C or not 2C: phenethylamine designer drug review". J Med Toxicol 9 (2): 172–178. June 2013. doi:10.1007/s13181-013-0295-x. PMID 23494844. 
  4. ↑ 4.0 4.1 "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochem Pharmacol 73 (2): 287–297. January 2007. doi:10.1016/j.bcp.2006.09.022. PMID 17067556. 
  5. ↑ 5.0 5.1 "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol 38 (1): 3–18. January 2024. doi:10.1177/02698811231211219. PMID 37982394. 
  6. ↑ "Kᵢ Database". 16 March 2025. 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=. 
  7. ↑ Liu, Tiqing. "BindingDB BDBM50240789 2-(4-Chloro-2,5-dimethoxy-phenyl)-ethylamine::2-(4-chloro-2,5-dimethoxyphenyl)ethylamine::CHEMBL124733". https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50240789. 
  8. ↑ 8.0 8.1 8.2 8.3 8.4 "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology 99: 546–553. December 2015. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. 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. 
  9. ↑ "Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function". Psychopharmacology (Berl) 231 (5): 875–888. March 2014. doi:10.1007/s00213-013-3303-6. PMID 24142203. PMC 3945162. https://www.researchgate.net/publication/258061356. 
  10. ↑ "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol 559 (2–3): 132–137. March 2007. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=00665d67c36dcf1777989b70cc901c654420a0c7. 
  11. ↑ "Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues". The FASEB Journal 36 (S1). 2022. doi:10.1096/fasebj.2022.36.S1.R2121. ISSN 0892-6638. https://www.researchgate.net/publication/360423277. 
  12. ↑ "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". Arch Toxicol 94 (10): 3449–3460. October 2020. doi:10.1007/s00204-020-02836-w. PMID 32627074. Bibcode: 2020ArTox..94.3449P. 
  13. ↑ "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther 357 (1): 134–144. April 2016. doi:10.1124/jpet.115.229765. PMID 26791601. 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. 
  14. ↑ 14.0 14.1 14.2 14.3 14.4 14.5 14.6 14.7 "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep 14. June 2025. doi:10.1016/j.toxrep.2025.101890. PMID 39867514. Bibcode: 2025ToxR...1401890G. 
  15. ↑ 15.0 15.1 15.2 15.3 15.4 15.5 15.6 15.7 "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol 95 (4): 1413–1429. April 2021. doi:10.1007/s00204-021-02980-x. PMID 33515270. Bibcode: 2021ArTox..95.1413K. 
  16. ↑ "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 zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  17. ↑ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016. http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php. 
  18. ↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista". https://www.finlex.fi/fi/lainsaadanto/2014/1130. 
  19. ↑ "20050026". http://www.notisum.se/rnp/sls/sfs/20050026.pdf. 
  20. ↑ "Erowid 2C-C Vault : Legal Status". http://www.erowid.org/chemicals/2cc/2cc_law.shtml. 

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